How to Answer Questions About Your Past Relationships on a First Date

“So … why’d the two of you break up?” she asked on their first date. “Was she cheating? Working too much? Not good enough in bed? C’mon, just tell me.”

“I, uh, well … it was, um, we had both started drifting apart,” he said before taking a large gulp of his wine.

Uncomfortable? If you said yes, think about how much more uncomfortable you’d feel if you were the one on the receiving end of prying questions like these. And from someone you just met, no less.

Well, this happens more than you may think on first dates, which can be the reason why those first dates also become last dates. That’s because personal questions about past relationships aren’t generally appropriate for this stage of dating.

So, how do you respond to personal questions about your past relationships when that not-so-special someone asks them? I have a few ideas.

Gently try and change the subject.

How open you are is a matter of personal preference. But as a matter of course, it’s usually better not to divulge too many details, especially about matters of the heart, to people who don’t know you well. That’s because they have no frame of reference by which to evaluate your comments, and you risk them getting the wrong idea about you.

Therefore, if your date starts to press you about information you may not feel comfortable discussing, your best bet is to try and gently change the subject. More specifically, direct the conversation to subjects you may be more comfortable talking about: your travels, where you grew up, your livelihood (in broader terms), and perhaps some of your aspirations.

What each of these conversation topics has in common is that you can approach them from a place of positivity. Past relationships, no matter how well they ended, can bring about negative emotions, such as sadness or anger — in you and the person you’re speaking to.

Come out and say that you’re not comfortable discussing your past relationships.

If the person you’re on a date with isn’t taking the hint, consider taking a more direct approach: “I’m not really comfortable talking about this. But I would love to hear more about how you …” And then ask them something about themselves. Or, again, try to divert the conversation elsewhere, perhaps to something you recently did or have planned. The important thing to remember is you don’t owe anyone an intimate view of your life, especially someone you recently met.

Now, I will warn you, there are those people who still won’t listen and will continue to press you. If the person you’re out on a date with still doesn’t want to honor your request to change the subject or just isn’t getting it, they’re giving you information about themselves that you need to carefully evaluate.

Make a decision about whether you want to consider dating this person.

At the extreme, if someone is making you uncomfortable on a date, whether because of the personal questions they’re asking you or any other reason, you always have the right to excuse yourself then and there.

However, if you don’t feel as though you’re in imminent danger but find their persistence anywhere from annoying to off-putting, you have a decision to make: Do you want to see this person again should they ask?

Having someone pry into your personal life, even after you’ve requested clearly and directly that they stop, could be a red flag and a sign of undesirable behavior to come. For example, this person could be controlling or emotionally abusive. Think about it. If they’re pushy about your past relationships at this stage of the game, what else will they be aggressive about, and when? You don’t need to wait around to find out.

Final thoughts …

First dates are the time to begin getting to know each other. The time when you can learn as much about a person from their answers to the questions you ask as you can from the way they ask questions, the type of questions they ask, and their reactions when they don’t get their desired response. I know it’s a lot to discern. However, it’s critical that you take a moment to assess what it is you’re learning from and about your date.

Your time is valuable as is your physical and emotional wellbeing. So watch and listen. Then, if you don’t like what you’re seeing and hearing, feel free to move on. There’s no shortage of eligible singles — if you have the right advice to guide you. Singles who will show you the courtesy and respect you want. And are waiting for you to show that to them, too.

Cassie Zampa-Keim is dedicated to helping singles find their perfect match.

1. How did I get into the business?

After college, I wasn’t sure what I wanted to do. But I was (and am) a people person. I like to get to know what makes others who they are and how I can help them improve their lives. I had an opportunity to apprentice with a local matchmaker, so I gave it a shot. It didn’t take long to find my true passion, which is finding love for singles. You could say that when it came to my chosen career, it was love at first sight!

2. What makes a client successful?

Commitment. Commitment to the process. Commitment to their goal of finding love. Commitment to themselves to be the best they can be. For clients to be successful at finding love, they have to be all in. We must work as a team, and they must respond to me. Clients have to have faith in the process and remain optimistic. Attitude counts for a lot. Potential matches can sense when someone’s negative and will shy away from someone who is. Positivity is an aphrodisiac.

3. What does a typical client look like?

This is the great part about what I do. None of my clients are typical. They range in age from their thirties to their eighties. They come from various backgrounds. However, there are commonalities, and they are that all of my clients are smart, successful, dedicated, and kind people who lead full lives but know their life can be fuller with the right partner. My clients are with me because they are invested in finding love and invested in themselves.

4. Why did I start doing the hot tips of the day on Instagram?

People were asking if I had one piece of advice for them what it would be. I’ve been in this business for more than three decades and, therefore, I have a lot to say. It’s also why I wrote my book, “Finding Love After 50.” This led to my hot tips on Instagram (@innovativematch). I realized people wanted practical yet inspirational information they could get while on the go. My hot tips took off because it was a way I could connect with singles and them with me while helping them change their lives.

5. Why does Cassie call her work a journey and not a program?

Finding love requires introspection and making incremental changes to your attitude, environment, and, how much faith you have in yourself. Transformation is a process and doesn’t happen overnight. Calling what I do a program implies there’s a start and finish and minimizes the magic that comes when you commit to yourself, which you must do to commit to someone else. A growth mindset is something you develop and can take with you wherever you go and benefit from whoever you’re with, especially a new love. Are you ready?

Want to Redesign Your Love Life? Here’s How

Did you know that you are very much in control of your love life? You may not feel like it, especially if you’ve had negative experiences online. When using online dating sites, it can feel as though you’re never in the driver’s seat. That you’re always at the mercy of others, waiting around for a response to your emails, texts, and calls. And that’s if you’ve even gotten that far. 

These issues may be accurate and, to some degree, probably are because, for starters, you can’t control anyone else’s behavior. However, because you can control your own, there are ways for you to put yourself in the driver’s seat and increase your chances of finding love.  

 The first has to do with defining your relationship goals, and the second deals with laying out a strategic plan for meeting as many people as possible. After all, you can’t meet potential matches if you’re sitting at home on your couch watching Netflix.  

So if you’ve been looking for love in all the wrong places or finding only the wrong people even in the right places, a redesign of your love life may be what you need. Here are a few ways to get started.  

Three questions to ask yourself to discover what kind of partner you want in your life. 

1. Would I date myself? 

It sounds like a silly question. In fact, the idea of dating yourself might seem strange — and perhaps a bit narcissistic. But asking yourself this question and exploring the concept could give you insight into why your dating life isn’t going quite as you’d like. If, for instance, you find yourself attracting the wrong kind of person.

Before entering a relationship, you should want to date yourself. If you want someone who has plans for the future, you better first have some of your own. Do you want someone sensitive, responsible, and compassionate? These are wonderful qualities, but are you this person, too?  

It’s hard to ask something of someone you wouldn’t (or couldn’t) ask of yourself. If you wouldn’t want to date you — the real you, then the people who do might be, let’s just say, less than optimal partners. Therefore, it may be worth asking: What about me would I like to change to make myself more attractive to the people I want to date? 

That said, I am by no means advising you to take on the qualities of someone you meet. No, not at all. What I am suggesting that you do is take affirmative steps to become your best self. There’s a difference. 

2. What kind of relationship am I looking for right now? 

Nothing is worse than finding a great partner only to realize you are looking for different things. To avoid the heartbreak and frustration of a “right person, wrong time” situation, it is important to recognize your own needs and objectives in a relationship.  

Are you looking for something more low-commitment? Then you should make that clear to the people you go out with so they know what to expect. Are you ready to settle down? Then you may want to avoid people with “nothing serious” in their online dating profiles.  

Getting clear with yourself first about your relationship goals will enable you to better communicate them to a potential partner. It will also ensure that you find someone with the same objectives.  

3. What has worked for me in my past relationships, and what hasn’t? 

This question goes hand in hand with my first two points. Are there issues you struggled with in your past relationships? Did you, for example. have trouble communicating or trusting past partners? Alternatively, were there characteristics of past relationships or partners that you liked and would want to see in a new relationship?  

Get clear about what your past relationships lacked and why they were wonderful while they lasted. Next, look to the possible reasons behind why for both. Finally, look for ways to make improvements in a new relationship.    

How can I expand my network and increase my chances of finding love? 

1. Get active! Join activities/classes to meet new people. 

Whether it’s joining a gym or taking a class at the local community center, getting involved in an activity is an effective way to meet people with similar interests. You can also see if your workplace, parks department, or house of worship has a recreational sports team you would be interested in joining. Not only are sports a great way to stay active, but you may also be surprised by the people you meet.  

Don’t think you’re the active type? Look to join a local book club, movie club, cooking club, or hiking club. Whatever hobby you enjoy, others probably enjoy it, too. And that makes for a natural starting point for a friendship, romance, or friendship that leads to romance. 

2. Call up friends to catch up. 

Friendships are like plants; they will wither away and die if you don’t water them regularly. So make sure you periodically reach out to your friends.  

Call or text them just to see how they are doing. Ask about your friends’ lives. Show an interest — and genuinely be interested — in what’s important to them. A good friend doesn’t make a friendship all about their needs but also takes an active interest in the other person. 

 Building genuine friendships naturally expands your network and can open up opportunities for you to meet a potential love interest. Your friends may know and be able to set you up with someone they know you would get along with, and because you are such a good friend, they will be only too happy to do so. 

3. Say yes to new adventures and events when invited.  

Reasons abound for why you may not want to go out on any given night. Maybe you’re tired after a long week or have a lot going on at work. That said, if someone invites you somewhere, you should make an effort to go. Even, or especially, if the event in question is something you have never gone to before or an activity you haven’t tried.  

Obviously, if the activity in question is something you don’t feel comfortable doing or you can’t afford, you should probably decline the invitation on those terms. But do try to make alternative plans with that person. But, again, the point is to stay active and engaged with your network. And most of all, open to what your interactions, energy, and what having a positive attitude can bring you. 

For the Founder of This Matchmaking Company, Her Life's Work Is Also Her Passion

1. Why did you hire Cassie?

 EMILY (Cassie’s client): I had tried online dating many times and never got results. I was on Match and Tinder but kept seeing the same guys. I also kept picking the wrong guys. The whole thing seemed futile. I knew it had to be something I was doing because people were still finding love. I never once thought of using a matchmaker, but I kept seeing Cassie’s ads, was curious, and figured I’d reach out. 

2 . What did you gain in value from working with Cassie?

EMILY: Cassie responded immediately. I was nervous, but I knew that I would be hiring a true professional matchmaker and seasoned dating coach as I was talking to her. I wanted someone with a fresh set of eyes who could weed out the guys, had a knack for picking not only the right guys but the right guy for me, and who could offer step-by-step dating advice. Cassie found Sean for me, and I’m so happy now.

3. Why were you successful with Emily?

 CASSIE: From the moment I started working with Emily, she was 100% in it, dedicating herself to the process by being open and positive. She listened to my advice and experienced a lot of personal growth as a result. She learned about herself and how important having similar core values is in finding a partner. We developed a great friendship riding the ups and the downs together. The result was I found her Sean.

4. What can a client expect when working with you?

CASSIE: Innovative Match clients are a wonderful community of like-minded, kind, dedicated, educated, successful professionals who are open to new thoughts, ideas, and, most of all, the possibility of finding love. My work is my passion, and all of my clients get 100% of my effort and enthusiasm because I genuinely care and demonstrate how much I care by always making myself available to listen and guide them. I can do that for you.

Do you get frustrated if you don’t get a response when using online dating sites?

One of the most frequent complaints from users of online dating sites like Match and OkCupid is that responses are sporadic. In other words, you send out emails, and it feels as if they are going into a black hole, never to be seen or read. 

Well, there may be some truth to that. If you’re using online dating sites, there’s a real likelihood that you may be sending messages to someone who’s no longer there. Someone who is no longer active. Someone who met someone but never deactivated their profile, got busy, gave up, or never cared to begin with. Or the profile was fake. But that’s another story altogether, and if it was fake, better you never had to find out the hard way.  

Whatever the reason, the profile you’ve attempted to engage with is there, but the person behind it is MIA. The problem is no one told you, not even the dating site. So what should you do if you send out an email and don’t receive a response? 

1. Don’t take it personally. As I just said, online dating sites do very little to let you know if the owner of the profile you’re engaging with is an active subscriber or not. Numerous online dating platforms have faced lawsuits about this very issue. These suits specifically concern how many accounts are fake or inactive or accounts that were accidentally reactivated by the site when the user had deactivated theirs.  

2. Look for signs of life. On an online dating platform, that sign of life usually comes in the form of a green or yellow light that indicates the account holder is active or recently was. How active, though, you still may not be able to glean, given how many people window shop online.  

3. Check out when exactly the person was last online. In addition to the green or yellow light, many profiles include a timestamp of sorts underneath the name and location of the account holder to indicate when exactly the account holder was last online. Depending on the platform, it might say something to the effect of “Online now” or “Online 9 hours ago,” for example. Whatever the phrasing, look for this clue. If this information is missing, it may very well mean so is this person from the online dating world. 

4. Don’t get frustrated. I know; you’re already frustrated. It’s the reason you clicked on this article in the first place. But really, getting frustrated serves no good here. Employing online dating sites in your search for love is a means to an end. It’s a tool to help you, not the focus of your search, which means it shouldn’t consume you.  

None of these online dating platforms are perfect, and why you should use more than one (but no more than three) in your search. But if you do, you may want to try engaging with a more niche site, where you may not see the same people over and over. For example, if you’re using a site such as Match or OkCupid, which are more mainstream, you may want to consider an online dating site with a more focused community such as Jdate or Christian Mingle.  

5. Keep going. Online dating is a numbers game, which means you need to keep playing to increase your odds of winning. And by winning, I mean finding a first date and eventually a partner or a spouse. Your person. A real person. One who will answer your email on an online dating site, want to text and talk on the phone, and then want to meet you in person. It’s not magic, but when you find love and love finds you, it will sure feel like it is.     

7 Surefire Tricks for Writing a Standout Online Dating Profile

There are a lot of factors that go into writing a successful online dating profile. And not all of them have to do with the words on the page, though they, too, are important. One misstep, and it could be the reason why a potential match passes you by.

Instead, what you want your profile to do is cast a wide net while still including enough information that the reader can quickly determine if you meet their basic threshold for matchability. What you don’t want to do is disqualify yourself for something in your profile that isn’t actually an accurate depiction of who you are.

So, who are you? Well, you tell me. Or rather, tell your new love. So, here are a few tips on how to do it.

1. Write your profile when you’re in a good mood.

If you write your online dating profile when you’re feeling optimistic, your positive state of mind will jump off the page, literally. However, the same will happen if you’re negative; the person reading won’t be able to get away from you fast enough. I mean, would you want to date someone who makes some of the following statements, which, even worse, often show up in the first line of an online dating profile?

●       “I don’t know why I’m here.”

●       “Is anybody really going to read this?”

●       “My best friend told me I should try online dating.”

●       “I can’t believe I’m back on this site again.”

●       “I’m not sure why I’m doing this, but here goes.”

●       “I’m here to see what happens, but I don’t hold out much hope.”

I can say pretty matter-of-factly that I wouldn’t want to date you simply because you sound like you wouldn’t want to date yourself. That’s a swipe left, Bob. 

2. Say less, not more.

Don’t do what this writer did, which is to say way too much. The adage less is more applies to online dating profiles, too. Consider the following two statements:

My last relationship ended after I found out my husband was having an affair with my best friend from college. I’m still angry about it and trying hard to move on, so I thought I would get on this site.”

“ lost my job last October, and now I’m thinking about starting a new career since I haven’t gotten any leads yet, probably because of the current administration. Lol.”

Neither of these narratives is suitable for a first date, let alone an online dating profile. Both reveal far too much information about the writer’s life, don’t reflect positively on the writer, make the writer sound negative, and, especially in the case of the second statement, can be polarizing.

And that’s despite the “Lol,” which does the opposite of what the writer probably intended it to, and that is to draw attention to the statement while making themselves otherwise sound wishy-washy (read: passive-aggressive) about their political leanings.

3. Be truthful.

If you’re separated, say so. Separated isn’t divorced. If you have a Jewish divorce, a get, Mazel Tov, but, remember, you’re still married under U.S. law. The same is true if you’re separated, but your spouse doesn’t know about it; “technically” married is still married. The last I checked, you can’t be a little pregnant either.

If you’re 67 and look much younger, again, congratulations. But your chronological age is still 67, so don’t put 54 in your profile because people say you look like you’re 54. Lies by any other name (“I changed my age for search purposes) are still lies. Same for height.

When you lie, and people find out about it, they tend to feel duped. They also tend to wonder what else you may be lying about. They also tend to send you packing.  

4. Focus on what’s on the inside, not the outside.

Do you know what’s sexy? Self-confidence. Being an interesting person. Independence. Knowing what you want. Do you know what’s not sexy? Focusing on someone’s looks, beginning with your own.

The reason? Who you are is so much more powerful than what you look like. Have you ever noticed that a person, regardless of their appearance, becomes better looking as you get to know them and find out you enjoy their company, think they’re smart, respect their values, and can see what a kind person they truly are?

The reverse is also true.

5. Tell a story.

Writing your profile as a story, with a beginning, middle, and end, while weaving in elements of what qualities you’re looking for in a potential match can be pretty effective. First, it keeps the reader engaged. Second, the technique gets readers to want to know more. And third, it’s specific enough so that the reader has enough information about whether they want to pass on your profile or engage.

The idea is that your online dating profile stands out from the others. Telling a story — your story — is an easy and fun way to do that.

6. Run your profile by someone else before posting it.

Before posting your online dating profile, ask a few people to read it. They should be people you trust, who will give you their honest opinion. Look for readers from your target audience, too. They may be able to tell you something different than your best friend or your mother.

If you’re not comfortable asking anyone, then try this: read your profile aloud. Do it anyway even if you’ve already asked five people to be your guinea pig. Often when you read a piece of writing aloud, you can hear your speech differently than if you read it to yourself. The idea is to come off conversational and relatable, and sometimes you need to hear what you wrote to do that.

7. Proofread, edit, and spellcheck.

The idea is to engage your readers by having them focus on the positives about your online dating profile and, obviously, you. Not engage them because your profile is so bad they can’t bear to look away from it.

Poor grammar, bad editing, and spelling errors are huge deterrents to readers. They may read to the end simply because it’s that horrible or decide to keep scrolling by the second sentence. Either way, the outcome isn’t one you desire.

In this day and age, any mistakes in your profile are on you. Which means you hold the key to a great profile. And your heart.

Don’t Talk Yourself Out of a First Date. Here’s Why.

Have you ever scheduled a date with someone new and had second thoughts? Said to yourself or someone else, “Why am I even bothering to go?” 

If you answered yes, your response is normal. Summoning the strength to go on a date is no easy feat. It can feel like a lot to have to get dressed, drive to a location you may not have been, then be “on” for an hour or so with someone you’ve never met in person before. I’m tired just writing about it. 

But, and this is a big but, if you talk yourself out of going on that date you scheduled (unless, of course, there’s a really good reason, like you found out the person is married or has lied about their identity in some other substantial way), you may miss out on meeting your new love.  

Sound corny? You bet, but it’s true. I cannot tell you how many times I’ve gotten a phone call from a client right before a date, asking me how they could cancel in a polite way. I’ve received these calls sometimes within as few as 20 minutes before the date was to start. The biggest reasons? General disinterest and first-date jitters. 

Fortunately, I have advice for overcoming both. So, if this has ever happened to you, I suggest you continue reading.  

How can you overcome disinterest before a first date? 

It’s extremely important before a first date to make sure you’re in the right headspace. Otherwise, your date will feel like dominos falling, and nothing about the date or the person will fall into place. Your date, in other words, will probably leave you wanting more. Which means you won’t want anymore — from them, at least. Your relationship will have been over before it started. 

A way to become interested before a first date comes down to a few simple things, beginning with only scheduling dates with people you’re interested in seeing. That means, after a few text exchanges and a call or two, if you don’t want to meet that individual in person, then don’t. It’s not time wasted; it’s actually time saved. Your time is precious, and, therefore, you shouldn’t give it to just anyone. 

Once you’ve put that date on the calendar, prepare for it. If you’re the person planning the date, do your homework. That means considering your past conversations to pick a venue both of you will enjoy, one that isn’t too far away for the other person or remote.  

After that, generate excitement about the date — for the other person and yourself. Brush up on the details you’ve already learned about the person. And interact via text or a quick call before the date. Always confirm.  

If you’re not the one planning the date, still review what you know about the person you’re about to meet. Excite yourself. Imagine the potentially nice morning, afternoon, or evening in store for you. Think positively, instead of saying, “I know nothing’s going to come of this.” 

These few small actions will make you feel more invested. Not too much that you will feel disappointed if there’s no chemistry on the date. But enough that you’re setting yourself up, and the other person, to feel any chemistry that may exist.  

How can you overcome pre-first-date jitters? 

Doing most of the above will get the ball rolling for getting rid of or at least lessening those pre-first-date jitters you may feel. Beyond that, I have a few suggestions for taking the edge off. 

If you’re feeling nervous, make sure your internal narrative is positive. Remind yourself of all that you can offer to another person. Make a list if you have to of all the traits that make you appealing.  

Still a little jittery? Talk to a friend or a dating strategist like myself. Someone who can listen and let you bounce your fears or ideas off of. Sometimes it’s helpful to know you’re not alone in this. 

Finally, tell yourself it’s just a date. Take the pressure off of yourself. The only reason for a first date is to see if you like the person enough to move forward with them for a second date and to have fun. That’s it.  

Don’t go in thinking, “Is this person going to be my husband or wife?” That’s a lot of weight to put on a first date.  

My advice? Keep dating in perspective. It’s just that simple. And easy. Which is how dating should be.  

Should You Date Someone Who Has Never Been Married?

He’s afraid of commitment.”

“She’s crazy.”

“He’s set in his ways.”

“She’ll put spin class before you.”

And these are only a handful of the reasons I’ve heard why you shouldn’t date someone who has never been married. I’ve heard more, and none of them are necessarily true.

That’s because, when it comes to dating, the only rule you should stick by is that a rule which causes you to close yourself off from options is a bad rule. Here’s why.

When you see someone on a dating app, you have no idea why they’ve never been married.

Though I consider online dating a valuable tool for exposing yourself to a large pool of singles, some platforms, especially dating apps, are fundamentally flawed because they don’t provide a lot of space to explain your single status. Especially the “never been married” status, because that sometimes requires a bit more explanation.

For example, say a person was in a committed, long-term relationship, but that he and his partner decided, for financial reasons, not to marry. Does it mean he was afraid to commit? No, not according to these facts. Their agreement was mutual.

Consider also the lawyer who worked around the clock until she made partner during her tenth year of practice, then put in another five years because she wanted to solidify her position. And now that she has, she’s ready and has the time to devote herself more fully to a relationship. Is she crazy because she hasn’t been married yet? Crazy busy, yes. Nuts? I would need more evidence of that.

Or the guy who had several short-term relationships that didn’t work out, whether because of a lack of chemistry, a job transfer, or a sick parent who ate up a lot of his time and attention. Is he set in his ways, or did life get in the way of him finding a partner? Chances are it’s the latter.

And about that woman who loves spin, who missed going to the gym during the pandemic, and whose Peloton changed her life. Yeah, she loves spinning for sure. But would her love for it supersede her finding the love of her life? I’m doubtful.

The point is I could come up with hundreds of scenarios, each of which could explain away the limiting statements above. Statements that could cause you to miss out on meeting an entire category of people based on one thing they haven’t done, which is to marry, versus all the things they have done in their lives to make them the person they are and why they may be right for you including the fact that they’ve never been married.

Here are a few benefits to dating someone who has never been married:

●        Less time and fewer financial obligations they must devote to an ex-spouse and kids, for example

●        Less emotional baggage, such as lingering anger or resentment from a nasty divorce

●        More flexibility since fewer obligations and less emotional baggage may lead to having more time to spend with a new partner, added freedom to move closer to them, etc. 

Final thoughts…

I have a friend who always says, “She/he fell through the cracks.” What my friend really means is that the person they know is great but just hasn’t met their person yet.

If that’s you, the one who has fallen through the cracks, say, as Michael Bublé did, it’s because “I Haven’t Met You Yet.”

And if, by chance, you have been married but find yourself on a dating app because your last relationship or marriage didn’t work out? Remind yourself that it also means you haven’t met your person yet, either.

5 Ways to Up Your Message Game and Improve Your Online Dating Success

Feeling tired of messaging on dating apps and getting nowhere? I have a simple answer: stop. No, don’t stop messaging. Rather, start making the most of your messages. 

Messaging, no matter how much we loathe it and how it can make the early stages of dating feel tedious, boring, and frustrating, is necessary. That’s because online dating is ubiquitous. So, too, are the messaging platforms they have built into them.  

Even if you hire a matchmaker/dating coach to strategize with you, online dating is still the most effective way to access singles. The idea is to narrow your search from there. How you interact when messaging is one way to judge and be judged by your single peers. 

So, if your messaging skills need some improvement, listen up. I’ve got five easy steps that can take you from digits to date.  

1. Don’t give out your phone number in the first message. 

If someone wrote to you, “Hey, here’s my phone number. Feel free to text or call me,” what would you think? Probably that (1) this person is way too aggressive, (2) they’re desperate, and (3) they’re likely sending this message to a lot of people, not just you. Feeling special yet? 

Probably not. Well, that’s more reason not to send this kind of message to others. The idea is to engage someone you’re interested in with a message, not chase them away with one. 

2. Personalize your messages.  

So how do you engage? For starters, personalize your messages. If you’ve seen someone’s profile on a dating app, reference a detail you read about them from it. The message doesn’t have to be long. In fact, it’s better if it’s short. Ask a question to get the conversation going. 

Think about your first exchange as building blocks. If you were building a foundation for a building, you wouldn’t throw a bunch of cement blocks in a pile, would you? The same goes for messaging. Think slow and steady. After all, you want to build rapport between you.  

3. Pay attention to the rhythm of your exchange. 

During each exchange (there could be a few messaging “sessions” before you take your interactions to the next level with a phone call), pay attention to the rhythm of your messaging. What does this mean? If you send one message, wait for a response. When the person you’re messaging sends back one, two, maybe even three short messages, then respond.  

Don’t write volumes. Balance the length of your messages with those from the person you’re messaging. And, heaven forbid, if the person you’re messaging drops off or doesn’t message you back right away (or ever again), don’t blow up their phone with “Hello?” or “Did your cat get run over?” or “I guess it’s over.” 

I shouldn’t have to explain how you sound. Okay, since you asked, I will: #psycho  

4. Offer to chat. 

Messaging can be fun and a total rush as you see the name of the person you’re interested in pop up on your home screen again and again. But it can also get old fast, especially if you’re messaging someone on the other end who’s on the dating site because they’re serious about meeting potential matches, not finding other messaging buddies.  

So, if after a few exchanges, you’re interested in talking on the phone, offer to chat. If the other person dodges you and continues to strike up conversations over the dating app, ask a second time politely. Don’t wait too long to make this second request. Your time is valuable.  

If they still don’t take you up on your offer to speak the next time you ask, take that as your cue to move on. Then do so without drama. 

On the other hand, if the other person says they’d like to talk, pat yourself on the back because it means you’re doing this messaging thing right. And you’re also ready for the next step, which is to . . .    

5. Exchange phone numbers and schedule a convenient time to talk. 

Convenient should be the operative word here—for both of you. You want to talk when you have each other’s attention.  

So pick a time when you’ll be at your best. When your boss isn’t within earshot, you’re in aisle ten at the grocery store, or you just had a fight with your ex or teenage son. 

Blow it, this call could become your first and last call with them. Better yet, it could be the call that leads up to your last first date. 

5 Reasons Why You Should Be Frickin’ Happy You’re Single on Valentine’s Day

It’s coming…The day dreaded by many singles, men and women alike. What to get the wife, husband, girlfriend, boyfriend, activity partner, or new squeeze can the source of a lot of stress. And suppose you get it “wrong”? Let’s not go there now. 

Then there’s all that well-meaning advice and the articles about what to do on Valentine’s Day if you’re single or how to celebrate Galentine’s Day. If you’re like a lot of singles, you just don’t want to hear it. For good reason: there’s nothing wrong with being single on Valentine’s Day. In fact, it can be quite right. Here’s why. 

1. You’ve ended a relationship because it wasn’t working. 

Whether you ended it or the person you were dating ended it for you, kudos to you. Why? There’s no better way to waste time than staying in a relationship that’s going nowhere. Or a relationship that isn’t making you happy, where you feel unseen and unheard. Or worse, a relationship in which you’re the victim of abuse.  

These are all great reasons to be single, and you should celebrate them this Valentine’s Day. And every day after.  

2. You’ve decided to take time to work on yourself. 

“It’s not you, it’s me” is your mantra. You’re keenly aware the time isn’t right for you to be in a relationship right now. Whether you’re changing jobs, want to focus on your career, are resolving issues from your childhood, or are knee-deep into a kitchen renovation, which is stressing you out, it’s all good.  

Everyone, including you, is entitled to take time off from dating to focus on yourself, to improve your life in any way you imagine. That can include going to therapy, visiting a spa, or anything in between. Your life is your life, so live it on your terms. Better to date when you’re ready.   

3. You’re enjoying your single status now.  

Being single can be freeing. It can feel liberating, especially after the end of a long relationship or marriage. Everyone needs space to heal and to regroup. The same is true if you’re suffering from dating burnout. A break can be just what you need.  

Being single, you can take to time to figure out who you are, what you like, what you don’t, and what you’re looking for in a new partner. That way, when you meet someone you’re attracted to, you can make an informed decision about whether you want to explore a relationship with them. The best part is you can have fun while doing all this.  

4. You’re keeping your options open.  

As someone who’s single, you have nothing but options. Opening yourself to all of the possibilities out there (there are so many singles to meet these days) means you have not only the freedom of choice, but you hold all of the power.  

They (whoever they are) aren’t choosing you; you’re choosing them. This state of mind in itself is empowering. Strong, confident singles attract like-minded people, which is definitely a plus. 

5. You recognize that finding the right person for you is a process. 

You might have heard that dating is like having a second job. I don’t really love when people say that because having a second job can sound tiring or imply that dating is a burden. Dating is anything but that. That is if you’re doing it right. 

I tell my clients to think of dating as an activity — a fun one. You wouldn’t sign up for spin, pilates, or photography if you didn’t like it, right? With that in mind, a date should be enjoyable and something you look forward to. If it’s not, then the situation isn’t right: the person you’re meeting isn’t someone you’re interested in, what you’re doing together isn’t something you like, or you don’t have your head in the game.  

All of these reasons are worth hitting the pause button to ask yourself: Am I spending the time I’ve allocated to dating constructively? If your answer is no, change the dating venue, the date, or the person you’re going on the date with. But, most importantly, change the narrative in your head. Once you do, your heart will follow. And whenever you’re ready, so will the person who’s right for you. 

5 Things to Do if the Person You’re Dating Says During a Breakup ‘It’s Not You, It’s Me’

You’ve heard countless times of people who’ve gone on several dates and think it’s going well, only to be blindsided by the other person who says they’re no longer interested in moving forward. Or perhaps sensing that the interest of the person they’re dating is waning, they send a text asking if their suspicions are correct, only to get the confirmation they seek. Or they send an innocent text asking to hang only to be met with the same result, that it’s over. Maybe these things have happened to you.  

How easy it would be if the dumper left it at that. “We’re done.” “It’s over.” Unfortunately, there is one phrase dumpers use that tends to cause confusion for the dumpee and, as a result, unnecessary pain and the wasting of precious time. And that is: “It’s not you, it’s me.”  

Having been helping clients navigate relationships for more than three decades, I’m here to tell you that these five seemingly “nice” words are, in reality, the death knell of not only your relationship but – and here’s the clincher – of any hope that the relationship will pick up again.  

Repeat what I’m saying to yourself again if you have to. Because what I’m desperately trying to prevent you from doing is what so many people do when they hear these words, and that’s to hang onto the phrase as a shred of hope this person will eventually come around. Reader, if this behavior describes you, you’re grossly mistaken.  

Arguably the most cliché of the breakup-isms, “It’s not you, it’s me,” comes up again and again for me with clients. If they haven’t had it said to them, they’ve used it on others. Although everyone knows it’s cliché, it remains a dating go-to because, in theory, it appears harmless. Even nice because it places the blame for the relationship’s end on the dumper, so, hopefully, the dumpee doesn’t feel as bad.  

The problem is that it doesn’t work for two reasons. First, the person getting dumped still feels bad. And second, they think there’s hope. 

Despite intentions, the meaning of “It’s not you, it’s me” is actually this: “It’s you, not me. I don’t want to hurt your feelings, but I want you to go away as soon as possible, and even better is if you go away quietly.” Unfortunately, that message doesn’t usually come through loud and clear. Instead, what happens is the dumpee believes, in error, the dumper will come around when the timing is better for them.  

But what about your timing? See where I’m going with this? Take it from me, the words “It’s not you, it’s me” give you all the information you need to know — it’s over now. Not for now. But now. And now has to be enough of a reason for you to move on. Time is precious. Time also equals opportunity, something you never want to squander.  

I know what you’re going to say. Their mom is sick, they’re changing jobs, their kid is going through a rough time at school. You’re happy to wait it out. Stick by them. You’re a good person, and so are they. 

I hear you. But you need to hear the person who just dumped you, and they don’t want you doing that. Otherwise, they would’ve told you so. They would’ve asked for you to stay or simply not let you go.  

 I understand that it’s tough to hear. Which is why I have five tips that can help you move forward. 

1. Take the words at face value. 

This isn’t a rom-com. This is real life, where most people say what they mean, even though they might not say it firmly or loudly enough. But actions? Actions speak for themselves.  

So think about this: a person who wants to keep you would never want to put you in a position where they could lose you. On the contrary, they would do everything in their power to keep you close. The last thing they would ever want you to do is date other people. Remember this, if nothing else.    

2. Understand it’s also you.  

We’ve all heard about the person who received the “It’s not you, it’s me” breakup line, only to watch their ex meet someone else shortly after the breakup and give that person all the things they couldn’t or wouldn’t give to them. Again, this might have happened to you.  

The reason why this happened? When someone says, “It’s not you, it’s me,” it really is you because, for the right person, people move mountains. They make sacrifices. Again, they do everything not to lose the person they want.  

There are exceptions. But exceptions aren’t anything you can count on. Don’t live for exceptions.    

3. Tell them you understand. 

If you’re on the receiving end of an “It’s not you, it’s me” breakup speech, tell them you understand, even if you don’t. Even if you think they’re confused, that you can convince them otherwise, that what they’re saying is wrong.  

Because, even if, by chance, you can convince them to stay, it will probably be short-lived. Instead, do the following. 

4. Leave the conversation (and the relationship) with dignity. 

Don’t prolong the inevitable. Say your goodbyes politely, and then go somewhere else to lick your wounds, process the breakup, and give yourself the closure you crave.  

Stop yourself from begging. Don’t cry. But do leave with your head held high. You want someone who wants you. You deserve that. Then…    

5. Move the #@*% on.  

Take time to heal, but not too much time. You don’t want to wallow in sadness and stay stagnated. You want to move the #@*% on. It’s easy to say, but the operative part of this is actually doing it.  

 Go no contact. Oh, they’re already not communicating with you? Perfect. Now stop following them on social media, asking mutual friends and acquaintances about how they’re doing, and keeping tabs on them, even if you’re not connected, but their profiles are public. In this case, again, it’s you, meaning you have all the power.  

So I ask you: what are you going to do with all of this power to now better your life? And, with it, your chances of finding the love you deserve? If you aren’t sure, call me. I have a few more ideas… 

3 Ways to Handle a First Date When There's No Chemistry

It’s not uncommon. You walk into a first date excited. You’ve done your homework. You’ve exchanged messages on the dating site where you met, traded texts, spoken on the phone a few times. You like their pictures. You have a lot in common. Then, as you approach, say your hellos, and begin to chat, your heart sinks. You’re not attracted to them. Or, your attraction wanes as the date goes on the more time you spend together. Your takeaway? There’s no chemistry. This isn’t your person.

So what’s a girl or guy to do? A few things, actually. And then there are the things you shouldn’t do. Why? Because that flat date of yours is still not dead in the water. Not because a spark may still ignite. In general, that’s not how attraction works, though there are exceptions when attraction can grow over time. But that’s a discussion for another day. The reason why this particular date still has value is that it can help lead you to the person with whom you do have chemistry, perhaps your future love.

So what should you do not only if you find yourself on a first date where there’s no chemistry but when (because it’s only a matter of time)? I have a few thoughts on the subject.

Be generous with your time and attention.

 Think about a first date as you would a job interview. Your goal during a job interview is to come off as calm as possible, no matter how nervous you are. When speaking with the person interviewing you, you would make sure to focus on what they’re saying, so when you answer them, you come off looking professional, composed, intelligent, and pleasant. In other words, someone they and the rest of their sphere – here, the people in the company – would want to know.

The same should be true when you go out on a first (or any number) date because it’s what common decency is all about, even if someone isn’t treating you as they should. At that point, all you have to do is politely excuse yourself and leave. Never stoop to anyone else’s level. But if all is well except for the fact you aren’t feeling chemistry, show them – and yourself – the respect you both deserve by behaving in a way that will make you proud and have no regrets later.

That means behaving in a courteous fashion. Being courteous on a date means showing that you value someone else’s time by showing up when you’re supposed to in a calm manner. It means speaking to another person in a pleasant tone, asking and answering questions, and listening to them.  

If you show up frazzled or appear disappointed or distracted on a first date, think about how you will make the other person feel or how you would feel if someone did that to you. Probably not great. So take the time to prepare for your date and flip your mindset a bit if you don’t feel chemistry for the person. Not only are you demonstrating self-respect by showing them respect, which they deserve because they’re a person, too, but the impression you leave could also help or hurt you in the future based on what the person you’ve met chooses to do with that information, which brings me to my second point. 

Be aware of what kind of first impression you’re leaving.

The first impression you make is often the last impression someone will have of you, especially with a date you don’t plan to see again. The first impression you make can also last for a long, long time. It’s the memory that a person will have of you for days, months, years, even a lifetime, once you part ways. And because of that, it’s the most important piece of information you can give about yourself.

What someone else does with that information – that first impression – may inevitably change your life. If the person you’re on a first date with, for example, doesn’t feel you’re right for them or accepts however disappointed they are that you aren’t feeling a spark, they may still want to pass your name along to a person they know who they think you will connect with. That may happen immediately, soon, or when you least expect it.

Or they could vouch for what a great person you are based on your time together should someone ask them. The alternative is much, much worse – knowing someone is out there who’s more than happy to tell anyone and everyone what a jerk you are based on the limited information they gleaned when with you. So make your first date experience count.

Be open to new connections.

Being open to new connections, whether on a first date, roaming the aisles of your neighborhood grocery store, or walking down the street, means having a positive mindset. It means realizing that every person you meet can bring some value to your life (and you theirs).

To fully embrace a positive mindset, first, allow yourself to enjoy the time you spend with your date, even if it’s not going to lead to where you once hoped or expected. You may just have a nice night, and that’s worth something. Next, there’s value in what you can potentially learn or gain from your experience together. That could come in the form of a restaurant tip, business advice, a movie suggestion, maybe even a blind date they set you up on down the road. The sky’s the limit.

No, I’m not suggesting you become an opportunist about dating, believing every experience will bring you something positive. Negative dating experiences offer something significant, too – lessons. There are no guarantees about what you will walk away with, but it will be something, I promise. I can also assure you that you won’t benefit from dating if you don’t date. And that with every date, you will get better at dating and envisioning all that it can bring to your life.

9 Questions Asked and Answered About How to Plan a Successful First Date

I have been in this business for more than three decades and still absolutely love what I do. My first job out of college was assisting a woman who made matches between local singles. At the time, there was no dating industry per se, only people doing this in their own area. How the industry has grown!

I love matching people who’ve lived in the Bay Area for years, are transplants, or are open to moving — anywhere! It’s never-ending excitement because every person and relationship is different.

Why do I continue to do what I do? In a word, passion. Not only do I have the experience after making matches and providing guidance for more than 30 years, but I also have a genuine admiration for the human spirit and how resilient it is.

That’s because I personally beat the odds in my 20s, surviving an illness that could have claimed my life. It caused me to prioritize what I wanted for myself, and always at the top of my list, no matter how many lists I made, was love. It still is. I want to give that gift to others.

So if you’re looking for love, and want to know more about how to find it, here are some of the most frequent questions I receive about how to plan a successful first date.

1. What’s the key to planning a great first date?

The key to planning a great first date is the planning itself. You should have already spoken to each other before your date on the phone, so if you’re the one planning your first outing, you should have a general idea about what the other person likes.

The most important point is to make a date easy. That means no hikes or venues that are out of the way or hard to find.

2. What makes a restaurant, bar, coffee shop, etc. a great location for a first date?

Atmosphere goes a long way when it comes to dating spots. I’m generally not a fan of coffee dates because people often take this to mean it’s OK to meet at a Starbucks, Peet’s, or some other chain that lacks warmth and is often crowded and loud.

If you’re going to go for coffee, choose a coffeehouse that has some personality to it, like Red Whale Coffee. Remember, this is a date and not your coffee break during the workday.

As far as a restaurant or bar goes, don’t choose a chain. Choose an intimate and casual but sophisticated restaurant/bar where you won’t run into a bunch of your friends.

I know you have your favorite hotspots. But stay away from them for a first date!

3. How can you overcome pre-first date jitters?

It’s very important to make a physical and mental change before a date. For starters, dress appropriately for the venue. Not too fancy, not too casual. It also means switching from your day mode to date mode, even if your date is during the day.

Women, you can do this very quickly by switching your lipstick shade, changing your shoes, and taking your hair out of a ponytail. Guys, remove your tie. Get out of your suit and into something more casual. If you’re short on time, just change your shirt.

So you feel more at ease, read over your date’s profile and any texts and emails you might have exchanged to remember small details about them. This will help relax you and your date, so you don’t feel so much like strangers to each other. 

4. What’s the most common thing people stress about while preparing for a first date? Any tips for overcoming it?

My clients often worry about what they’re going to talk about, that they won’t have anything interesting to say. But, again, if you do your homework before the date by brushing up on your information about them, you will feel more at ease. You can pick and choose, for example, from their list of hobbies or places they’ve traveled to spark a conversation.

People are also often concerned their date won’t find them attractive or they won’t find their date attractive. My advice is not to worry about attraction just yet. As far as you’re concerned, your only purpose on the first date is to get to know someone by having a conversation with them. In other words, keep an open mind and your expectations in check.

Another worry is running into someone you know during the date. If you’re that concerned, then don’t go to a spot where you’re likely to run into your friends or, worse, your ex. But after that, don’t worry. You can’t control who’s going to be where, so why waste your energy?

And to be honest, if someone happens to see you on a date, likely they wouldn’t think about it for too long because people are busy and involved in their own lives more than anything else. They don’t have time to worry about what you’re doing.

5. What should you bring to a first date? Or, alternatively, leave behind?

I think it’s unrealistic to tell people to leave their phones behind. However, I would recommend you silence it and certainly refrain from checking it while with your date.

If you must check your phone, excuse yourself and go to the restroom to look. Do bring a positive attitude to your date while leaving your hectic and stress-filled life behind.

6. What topics should you broach on a first date? Stay away from?

Look for common ground when choosing what to talk about. Do you both like to work out? Travel? Go to art museums? Those topics are all fair game. You can talk about your kids but in moderation. You’re on a date, not them.

As for talking about your ex, past relationships, politics, and sex? Don’t. Light and breezy should be the standard. But remember to be conversational and to listen. This isn’t a Q&A session.

7. What are some first-date don’ts?

Don’t cancel a date unless you absolutely have to. It’s hard to take the word of someone you hardly know, and the person you’re canceling on may internalize the reason. Not to mention, they may be disappointed.

Never cancel over text; it’s just rude. If you must cancel, text to see if you can give them a quick call. The person can then hear your voice and feel your sincerity about why you’re canceling. And if you’re genuinely interested in rescheduling, do so then.

Also, don’t speak negatively while on a first date, ever. Don’t talk badly about your ex, your job, or the world. You will only come off as angry and unpleasant.

8. If your date isn’t going well, how can you politely (and safely) extricate yourself?

First off, don’t schedule a long date for the first outing. Forty-five minutes to one hour should be the max. Doing so will make it easier to extricate yourself if you have to. Dinner or lunch is too long.

To end a date politely, finish your drink but don’t order food. Tell your date it was nice to meet them but that you have to go. Thank them for meeting you. Then go your separate ways.

9. If your date is going really well, how can you make it clear you want to see this person again without coming on too strong?

If you’re a woman and you enjoyed your date, but the guy didn’t say anything at the end about seeing you again, but you would like to see him, send a quick text the following day telling your date you had a nice time. Guys, do the same.

You will be able to gauge by the response if your relationship will be moving forward. I give this advice because too many times there are missed signals at the end of a date. 

Final thoughts...

It’s important to note that not everyone is looking for a spouse. Some people are looking for a long-term relationship, a companion, an activity partner, a romance, or some combination thereof. My role is to put people in front of you who you wouldn’t ordinarily think of as a possibility. My success also turns on my clients being open to a connection and ready to make one. As far as how many meaningful relationships have I sparked? Too many to count!

What remains consistent is that everyone — and I mean everyone — has a story. You have to love people to do what I do. You have to be able to read people, which I can.

Everyone has something to offer. I learn from every person I meet and tell my clients to look at dating the same way. I love making connections and seeing people happier than they ever were before. I love seeing people go from a state of fear to having faith that the process will work.

Most of all, I love getting the thank you calls from clients that my consulting changed their lives. Why not let me help you change yours?

'And Just Like That,' Sex and the City’s Reboot Shows Us What Love in Our 50s Is All About

Warning: Spoilers ahead.

Whether you rooted for Carrie and Big to get together or finally move on, it's hard to imagine a world without him in it. But their relationship, fictitious as it was, was one Carrie and many of us who drank Cosmopolitans at home with her, Charlotte, Miranda, and Samantha in the '90s can relate to. And one we can, in our 50-something-year-old bodies, learn from, especially about what love in our fifties is all about. And that's this.

Forgiveness

I admit, when the montage began to roll at Big's funeral, I teared up. The fault I found with his treatment of Carrie before they finally tied the knot suddenly faded into distant memory. John Preston was larger than life, and his life was over regardless of how I felt about it. 

A mourner in the show brought me back to reality, commenting about whether Carrie remembered how badly he treated her. I'm sure she did. But based on their easy banter before Big's final Peloton ride, she had clearly forgiven him. The only explanation I have for understanding the power forgiveness has to bring peace to one's life is age and the wisdom that comes with it.

Growth

Was Carrie wrong to forgive Big so many times, given what he put her through? If I were her guiding her, I would have likely told her to move on, with one caveat: he must demonstrate he's capable of change. 

Big indeed showed growth over the years. Most women wouldn't have hung in there that long, and there's a strong case for arguing Carrie should have left him years earlier or not let him back into her life every time he returned. 

It appears Carrie made a good bet even with terrible odds. That's because people in their fifties are capable of growth and maturity with the right tools. Big grew bigger.

Maturity

It wasn't only Big who matured. Carrie did, too. They also matured as a couple. 

I loved how they continued their pandemic tradition of playing a different album every night while making dinner together. They set aside time to be with each other, to enjoy each other's company without distraction. 

In our fifties, we know what the alternative looks like.

Acceptance

What our fifties reveal is that we're all flawed people. Because of that, the quality of the relationships we find ourselves in turn on how we manage the parts of our personality that make us who we are. Not only do we realize we're flawed, we understand we have to find the right person who will accept those flaws and embrace them. 

When we love, we must also love wholly. That includes the parts of others we perceive as both good and bad. Our deal breakers are personal. With our fifties comes experience and the ability to know what and who works for us — and doesn't. 

Resilience

No one gets to their fifties without experiencing loss. It's not a question of if we've faced it but, instead, how well we've learned to face our lives after losing someone we care about.

The time leading up to our fifties has shown us that love lives forever, even if the people who we love and who love us aren't always with us. We're changed — and stronger — for having known them.

Though Big is gone, I'm changed for having known him and the relationship he shared with Carrie, good and bad. And with that, I will continue to watch to see how Carrie goes on without him. Because that's what having love in our lives can do — carry us through.

How to Pick the Perfect Dating Wingman or Wingwoman

If you’re single, you may have heard that it’s a good idea to have a wingman or wingwoman in your life, especially when you’re out at a bar, restaurant, or locale where there are other singles. Well, you heard correctly.  

However, not everyone is qualified to hold the title. Like any other job, the person applying for it or being recruited by you must be qualified first. Picking the wrong person could actually decrease your chances of making a connection.      

So who do you pick to be your wingman or wingwoman? Here are a few things to look for. 

1. They make a good first impression. 

First impressions are everything. Therefore, the person you are with should make a good one. Everything they say and do reflects directly on you. After all, you’re out with them, and the power of association is strong.  

For example, if the person you’re with acts crass or has a sloppy appearance, you risk anyone you meet who doesn’t know you personally seeing you in the same light. Even if they don’t, the very fact you’re friends with this person could be cause for concern, if not be the reason why they walk away. 

Think of your wingman or wingwoman as a potential barrier to entry. In a good way, they’re there to protect you from those who may not be good for you. However, if they’re not giving off the right vibe, they could keep you from meeting those who are good for you. 

2. They keep their wingman (wingwoman) role on the down-low. 

Being a good wingman or wingwoman means being discreet about their function. They’re not a bouncer, after all, or your P.R. agent.  

Their value rests in them making you feel more relaxed as well as making connections where you may feel too shy or too inhibited to do so yourself. This brings me to my next point.  

3. They’re social butterflies. 

You know you’ve found a suitable wingman or wingwoman when that person is comfortable striking up easy conversation with anyone and everyone. They know a little about a lot of things. They’re good conversationalists, which means they’re good listeners, too.  

They like to chat people up and bring multiple people into a conversation. They’re inclusive and don’t feel the need to monopolize an exchange, making them the center of it. Most of all, they’re happy to make introductions.  

4. They’re the perfect amount of persuasive. 

A good wingman or wingwoman has a high E.Q. They can read people and situations well. So if they’re trying to chat someone up, but that person appears uninterested, they know it’s time to move on. They know rejection is part of life and don’t sweat it.   

On the other hand, if they see a spark of interest, they run with it. But they do so without becoming too pushy or creepy. Instead, they ingratiate themselves in just the right amount. 

5. They’re involved romantically and happy with their situation.  

The best wingman or woman, and perhaps the most important characteristic they can have, is that they’re high on dating. They’re positive about romantic relationships, likely because they’ve seen the power of a healthy one firsthand. Even better if it’s in the present. 

Both points are critical. The first, because positive people send out positive energy. What could be more powerful than someone who believes in love? The second, because you don’t need competition by your side. That never makes for a fun, relaxing environment, which is the best kind to meet someone in. 

People involved in happy, healthy relationships themselves know that a strong relationship is the root of their happiness and want those they care about to experience the same. So it bodes well for them advocating harder on your behalf.  

Your wingman or wingwoman should also be a little selfish — but in a good way. They should know great couples friends are hard to find and want you and your future love for dinner plans and mixed doubles.   

Your Top 5 Holiday Questions Asked and Answered

It’s hard not to think of dating at holiday time without thinking of Bridget Jones in the iconic ’90s movie Bridget Jones’s Diary. Making the rounds at holiday parties single, the endless questions about her dating habits, and, of course, too many awkward moments to count. It all felt a bit much for her.

Remember the holiday dinner, everyone around the table a couple, where a prying dinner guest asked Bridget why there are so many unmarried women in their 30s these days? You could hear a pin drop as the entire table awaited a thoughtful answer, which never came. Because, after all, how do you answer a question like that without sounding (a) bitter, (b) insulting, or (c) just silly? Spoiler alert: There’s a way.

So continue accepting those invitations. As someone who’s single at holiday time, the last thing you should do is stay home. After all, you’re entitled to enjoy the holidays, too. Not to mention, the holidays can be a great time to meet people, either other singles or those who can introduce you to someone single.

Unfortunately, busybodies aren’t the only minefield to be wary of. There are exes lurking about, new relationships and hectic holiday schedules to be managed, and, not to be ignored, the age-old dilemma for the coupled about whose family to visit.

To help, I’ve answered the most common questions I get around the holidays about how to handle these sticky situations.       

1. What should I tell my friends and family about my dating life when they ask?

When family and friends give you the old, “So … how’s your love life going?” it’s really a personal decision about how much or little you want to say. But be prepared; there will be follow-up questions if you drop even the slightest hint of a new relationship brewing.

If you’re not looking to be in the hot seat around the holiday table, say something that will end the conversation politely, such as, “I promise to tell you as soon as I have something to tell.” If you prefer to be more open about your relationship status or lack of one, share away, realizing you may get questions later on about a special someone who’s no longer so special.    

2. My ex and I are both in town, but should we connect?

Ahhh, it’s so tempting. The lights, the mistletoe, the holiday cooking. But my answer is generally the same: leave exes where they belong — in the past. Even if you’re interested in seeing where things lead, tread carefully. Unless your ex has given you concrete evidence to think the reasons why your relationship ended no longer apply, you shouldn’t believe anything is different.

Connecting, in that case, will likely only lead you (and them) to pain that you both don’t need. It will also keep you from being in the positive mindset you need to meet someone new.

3. How do I introduce my new relationship during the holidays?

My advice is that unless you plan on being with this person for the foreseeable future, and they’ve indicated the same to you, I would refrain from bringing them home to meet your Mom, Dad, and dear Aunt Sally or meeting theirs. Creating familial connections too soon can create a false sense of intimacy.

It can also make it that much more difficult to go your separate ways, especially if you really like each other’s family and they’ve welcomed you both into their arms. In truth, family’s opinion or treatment of you has little to do with how the person you’re dating makes you feel and the depth of your relationship.  

4. How can I keep the person I just started dating interested while traveling solo over the holidays?

First off, don’t cancel your plans just because you’re seeing someone new. It’s very important to continue living your life and being independent. That said, now that you have a special someone, it’s also important to keep the connection going while you’re apart.

You can stay in touch easily by talking on the phone, texting, and FaceTiming regularly. Also, it’s nice to project and discuss any plans you may have or want to make when you see each other in person again. 

5. How can my partner and I decide whose family to visit for the holidays?

Deciding whose family to spend the holidays with can cause tension in a relationship, especially if you have to choose one or the other. If possible, and if distance and schedules allow, split the day. Dinner in one place, dessert in another. Or have two celebrations but on different days.

The point is to listen to your partner and be as fair with them as you expect them to be with you. After all, this is the person you’re supposed to care about, maybe even love, whose presence makes holidays — and your life — that much more joyful.

Holiday Gift-Giving When You’re Dating Someone New: How Not to Make it Weird

Is this even a possibility? Not making gift-giving at holiday time weird when you’re dating someone new or new-ish? No, not at all. If you choose your gifts right, that is. And get rid of some of the expectations you may have around gift-giving. 

It’s understandable how holiday gift-giving can become a nail-biting event. No one wants to be standing there with a gift that’s not in line price-wise with the one they’re receiving. The same goes for giving a gift that, although inexpensive, imputes depth to a relationship that may not be there just yet, at least for the person you’re giving it to.  

That’s why I’ve come up with a few tips to avoid feeling like you’re stuck in that wacky dream where you show up to work or class naked. After all, holiday gift-giving should be something you look forward to rather than fear. 

Get on the same page about gifts before the holidays arrive. 

A lot of the angst you may feel around holiday time surrounds whether or not you and the person you’re dating are on the same page. That’s is why I suggest having a conversation about exchanging gifts before the holidays, so you’re both on the same page about your expectations. 

Now, if it’s September and you’ve just started dating, it’s not time to project about what you’re giving each other. However, if your relationship appears to be going well and is on track to continue through the holiday season, feel free to bring up the subject casually around Thanksgiving.  

That could mean anything from suggesting to stick to a specific budget or price range to making a suggestion about the type of gifts you will be exchanging that you and, hopefully, they will be comfortable with. The point is you set up a plan.    

It may not sound romantic at first, but depending on how you position the conversation, you could make it so. First off, you can plan an activity to celebrate the holidays, such as attending a show or concert. Maybe one of you pays for the tickets, the other dinner.  

Or perhaps you propose the idea of setting aside a time to bake or cook your favorite holiday dishes together, watch a movie, and exchange something small? Or if you’re both on board, what about creating your holiday gifts? 

Buy two gifts at two different price points. 

So, you like surprises and aren’t comfortable having a discussion about holiday gift-giving in advance. But you absolutely have no idea what to spend. 

In this case, my suggestion is to buy two gifts, one at a lower price point and one at a little more significant price point but still commensurate with the length and depth of your relationship. For the former, I would suggest gifts such as scarves, slippers, pajamas, and books (this can include journals to write in). For the latter, I would recommend some type of electronic item, perfume or cologne, or a more luxurious clothing accessory. 

But here’s the catch: start out with the small gift. Then, based on what the person you’re dating gives you, decide whether or not you want to add the second part of your gift.  

The second gift should be nearby, in a drawer or a closet, for example. If you’re not home, leave it in the trunk of your car out of sight. You can always excuse yourself to get it. This way, you can keep your gifts around the same price point without making yourself or the person you’re dating uncomfortable. 

Decide beforehand there will be no weirdness about gifts. 

This is the option where you decide you’re going to let the situation unfold as it will. You tell yourself in advance that even if you give a much more expensive gift than the one you receive, you’re giving the gift you want because it expresses how you feel.  

The same goes for giving a less expensive gift because that’s what you can afford even though you wish you could give more, and the person you’re dating does give more. So be it. 

You’re confident in your own skin (and with the gift you choose to give) to not care about any imbalances in this particular instance. You see your relationship for what it is and know money doesn’t reflect the thought or time that can go into a gift. You also understand that a holiday gift is but one of the many ways people express how much they care about each other.  

Most importantly, you realize that making things weird over something as insignificant as a holiday gift early on in your relationship could mean the demise of your relationship. And that’s something you’re not willing to risk because having a quality partner in your life is in itself the best gift of all.    

7 Questions to Ask Yourself When Deciding Whether to Date Your Friend’s Ex

Maybe you never noticed them before. Or maybe you did, and now they’re available. The only problem is the reason they weren’t available before is that they were dating your friend.  

You care; you really do. But you can’t help but think that maybe, just maybe, this is meant to be. That the timing is right. That you shouldn’t have to pass them by just because it didn’t work out between your friend and them.  

Or should you?  

Deciding whether to date your friend’s ex is never an easy decision to make. But, pretty much regardless of what you choose to do, someone’s not going to get what they want, or worse still, someone’s going to get hurt. So what’s a single guy or girl to do? 

Ask yourself the following questions, of course. So you can make a decision — an informed one.   

1. What was the reason for the breakup?  

Do you know why your friend’s relationship ended? The reason could make a difference. For instance, if your friend was betrayed, if their ex cheated on them, you dating the ex could be seen by your friend as an extension of that same betrayal.  

Not to mention, if this person has a history of cheating on the people they date, even if it’s seemingly harmless activity such as micro-cheating, do you really want to be the one having to figure out if there’s anything to these minor indiscretions? Living on the edge in a relationship is no fun and will likely only lead you to the same fate as your friend, which brings me to my next point.  

2. Is there a chance your relationship could end the same way? 

If you think there’s a distinct possibility based on past behavior, current behavior, and whatever other red flags you can spot, tread lightly. The apple of your eye may, in fact, be rotten. Or, at a minimum, not ready to be picked. In which case, perhaps you should consider finding a different one.  

For example, if your friend’s relationship ended because of cheating, you may want to think twice. Though the adage once a cheater, always a cheater isn’t necessarily true, you should take a step back and look at the situation for what it is. And whether you want to take the risk history won’t repeat itself.  

The same holds for any other reasons why the relationship ended, including whether they treated your friend poorly, didn’t want to pay on dates, or displayed evidence of being a narcissist or someone with borderline personality disorder.  

3. How long ago was the breakup? 

You know how people say it’s all about timing in matters of the heart? Well, how long ago a person went through a breakup does matter. Not just because the person you have your heart set on might not be over the person they were dating. But because if you know the person they were dating, are friends with them, they could see you not only you dating their ex as a betrayal to them as I stated earlier, but, depending on how recent the breakup was, as a catalyst in their relationship’s demise. Neither of these situations bode well for you.  

With the first, you could be a rebound for them, which may mean your relationship will never go the distance and become a source of heartache for you because the other person’s heart and head will be somewhere else. As for the latter reason, do you want your friend to think you had anything to do with their breakup? Which brings me to my next question: Did you?  

Better to own your truth now than try and defend your actions later, after the damage has been done. To your friend and in the court of public opinion.    

4. Is your friend over their ex? 

Now, if you know for sure your friend is over the ex, then most of the previous situations don’t apply to you or matter. But how do you know your friend is over their ex? Don’t rely on time alone here. As we know, it can take a long time to get over a past relationship. The best way to find out is to ask your friend if they’re over their ex and if they would care if you dated them. 

While you don’t want to ask your friend for their permission, you should be prepared that your friend might take offense that you’re even asking and, even more so, at the thought of you dating someone they were once involved with. You need to be prepared for that possibility and what you will say to your friend. Much of that will come down to how you answer this next question.   

5. What is your motivation for dating your friend’s ex? 

This is the part where you have to get real with yourself. Why are you thinking about dating this person? Are you genuinely interested in them? Or is there another reason you want to date this person now, like are you trying to, for whatever reason, incite your friend?  

Depending on your feelings, you need to clarify with yourself whether you would be willing to give them up for the sake of preserving your friendship because, depending on what your friend says, you may have to. If what your friend says matters to you, that is. 

6. Is it important to you to have your friend’s blessing? 

Don’t just ask yourself how good a friend your friend is to you, but also how good a friend you are and want to be to them. Compare this question to the times when you ask someone in need, “Can I help?”  

Many times when people ask this question to others, they aren’t expecting the person to take them up on their offer. If it’s important to have your friend’s blessing, prepare yourself that they may actually ask you to step away from dating their ex. In other words, if you’re asking for your friend’s blessing, understand there’s a chance they may not give it to you.  

7. Is it worth losing a friend over if you don’t? 

If you don’t get the blessing you’re looking for, this is the time you must decide what you stand to gain and what you stand to lose, and which is worth more to you. There’s no guarantee either way. The only thing you can count on is that the decision won’t be easy. 

Is it True Once a Cheater, Always a Cheater?

“He’s perfect.”  

“She’s amazing.”  

You know, the person you just started dating. You’re asking the questions, and you like the answers you’re getting. Until you ask them that fateful question: “Did you cheat on your spouse?” 

You value honesty, so you appreciate that they’re truthful. But your heart sinks because you don’t like the answer: “Yes.” 

But is yes an automatic dealbreaker, especially if you’ve been cheated on before? You always thought it would be, but now that you’re faced with more than a hypothetical, you’re wondering if the adage is actually true, that once a cheater, always a cheater. Like most else when it comes to dating, my answer is that it doesn’t have to be. 

Dating dealbreakers are sometimes rules that can be broken, including a history of cheating. 

I’ve been in the business a long time. More than 30 years, in fact. And what I’ve learned is that to avail yourself of all opportunities, of all dating prospects, you sometimes need to live in the gray. In other words, you’re going to have to evaluate every situation for what it is. Which means not only will you want to listen to their story about why they cheated, but you’re going to have to read between the lines when you do. Then decide if your dealbreaker is a rule you’re willing to break.  

But before I get started about what you need to listen for, I want to be clear that I’m not advocating you settle. If after a discussion about why the person you’re dating cheated on their spouse, you don’t like what you hear, by all means, move on — as fast as you can. My advice is simple: give the person a chance to explain their past behavior, and why you should give them a chance. 

What you should listen for when deciding whether to date someone who has cheated on a former spouse. 

As we all know well, life is complicated. With that in mind, if a dating prospect explains they were cheating due to a specific circumstance you find is not only believable but also understandable, it’s OK to give them a chance. An explanation that resonates with one person might be completely offensive to another. Everyone has their own barometer about what’s acceptable to them and what isn’t. Figure out what yours is.  

The best explanation for cheating has little to do with the reason and a lot about regret.  

Some cheaters will have no explanation whatsoever other than to say they made a mistake. That they regret what they did and feel remorse for their behavior. These are often the best kind of people to date, despite their past cheating.  

That’s because they’ve processed the situation. They understand what they lost as a result of their actions, how they hurt people they love and loved, and how they hurt themselves. These are the people that would never want to cheat again. For them, they know there would be too much at stake. This is someone who, if you’re up to it, could be worthy of a chance.   

Final Thoughts... 

Cheating is one of the worst ways to hurt a partner. It’s a betrayal, and it can be life-changing for all of those involved — the cheater, the spouse, their children, extended family, and friends.. If you’re in a relationship, I don’t recommend engaging in this behavior, whatever the circumstance. Instead, I always suggest exiting the relationship in a transparent way.  

That said, no one can change the past. And I do believe people are capable of growth and chnage. That people are capable of remorse. And that human beings are capable of having compassion for someone they never thought they would once they know the full story. Therefore, the question you have to ask yourself when confronted with someone who once cheated is: “Am I at least willing to listen?”     

Why ‘Don’t Get Your Hopes Up’ Was the Best Dating Advice I’m Glad I Didn’t Take

“Why are you bothering?” Sue said.  

“You have us,” Tracy chimed in. “You have a beautiful house. Financial security. Why do you need another man in your life who’ll only end up disappointing you?” 

I sipped my chardonnay, then took another bite of my salad. Sue and Tracy had been around the block and back, dating after their divorces. Now in their late fifties, they were enjoying their singleness and couldn’t understand why I was still struggling. They thought I should be done with the whole lot of them, men that is, and live my life. 

My relationship with Steve ended before the summer started. It had already run its course long before it expired, but I hung on anyway until I no longer could. Until I realized I couldn’t change someone who wanted to stay the same, a man who didn’t want to acknowledge his addiction and how it was holding him back. 

My friends were right. I had all the things they said I did. I had a great life. But the thing about having a great life is that I wanted to share it with someone. The right someone. At 58, and after two marriages and a long-term relationship, I still hadn’t found him. 

Unlike my friends, in the back of my mind, I still believed he was out there. The problem was my energy for looking for him was low. Disappointing as it was to me, I felt I was starting to lose hope.  

I’ve never been a hopeless person. My faith in God always gave me the confidence I needed to believe, even in the worst of times, that my life would always get better. That opportunity — whether a new job, a new guy, or a new attitude — would be just around the corner. I had the trust I needed in God to provide for me. My hope, although somewhat deflated, floated me forward, lifting me above fear and uncertainty and into the realm of possibility.   

So, despite what my friends advised me, which was from their hearts and well-intended, I started to date again, this time with the guidance of a dating consultant and strategist. My friends’ choice, though right for them, was not for me. “Don’t get your hopes up,” Sue cautioned me.  

My first date was with a really nice guy. He was kind, smart, and interesting. He showed an interest in me, flying down from his home in northern California to meet me. We went out two times, but after the second, I realized I wasn’t attracted to him.  

I was disappointed and surprised when a slight episode of grief set in. Not so much because it wasn’t going to work out between us but because the experience took me one step further away from the long-term relationship I was hoping would work out but didn’t. It was really over. 

When I was done crying, something miraculous happened — I felt better. Energized, in fact. Despite the relationship not moving forward, I was going to. My next dating experience was with a guy I was really attracted to, a guy I found interesting, and one I wanted to get to know better. Our first date was fun, our second even better. My energy level rose yet again. 

But it wasn’t because anything in my life had changed. I was still single. I still went to bed at night alone. I still got invited to events solo, which is what happened when I arrived in Grand Teton National Park in Wyoming for my summer vacation, a place I travel to periodically, and where I went shortly after meeting that cute, new dating prospect of mine. 

Friends had invited me to attend a musical festival in the area. Feeling confident given my recent dating experiences, one which ended cordially, the other in its early stages, I invited a man I knew from the community who had lost his wife a year back. I thought he would enjoy the party, so I gave him a call and asked if he would be interested in joining me. He said yes. 

I went without any expectations but found I really enjoyed his company. I think he liked being with me just as much because we spent three days at the music festival together. We’ve been talking and texting ever since, even though I’m now back home. My energy level reached a new height, and I felt joyful. 

 Again, nothing in my life had changed. I remained single, I slept in the middle of my bed by myself, and I went out socially, uncoupled. Yet I felt better than I had in a long time. I had two men in my life who I liked and respected and was open to seeing where I was headed with either one. I was confident that whatever happened, even if nothing, that I was better for having met them. 

So when I went out on a date with a third guy following my trip, another super nice guy, I wasn’t afraid to tell him I didn’t think a relationship was in the cards for us. Although I liked him, I didn’t believe we had enough in common to grow into a couple, and wasn’t afraid to tell him how I felt. I hoped he would understand, which he did.  

And that’s when I realized why I had started to feel better, to have more energy, despite nothing in my life having had changed. It was the existence of hope. Hope that I would feel better following my breakup. Hope that I could find the courage to always speak my mind. Hope that I would one day meet a true partner. And most importantly, hope that no matter how much resistance I faced in my romantic life, or in any part of my life for that matter, that I could find the strength in myself, powered by God, to move forward.       

The 1998 movie starring Sandra Bullock as a divorcée suggests “Hope Floats.” Indeed, hope is an emotion that has a physical manifestation. It floats us up into the ranges of limitless possibility, energizing and lifting our spirit into the realms of serenity and joy. It’s a great place to be.  

This article originally appeared on Yahlight Blog on September 28, 2021.