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?