Seven Ways for Singles to Own Valentine's Day

Valentine’s Day can be so much fun because, let’s face it, it’s exciting to celebrate love. But every year for some singles it’s a challenging holiday that shines a spotlight on their single status. With New Year’s just past and many singles’ newly minted resolutions to find someone this year, I look at Valentine’s Day as the time to get started on those resolutions.

 I have been in the matchmaking industry for almost thirty years, providing dating and relationship strategies for single women and men. February is an exciting month for my clients as I work with them to conquer their doubts about finding love and help them launch back into the world of dating. Most of my clients have been divorced or widowed, so it truly is a trip back to something they did years ago, when their lives were very different.

 It’s normal to feel insecure about trying something again after a couple of decades. You don’t look like you did back then (by the way, neither does anyone else you’ll be meeting). Having gone through the loss of divorce or widowhood can make you hesitant to invest in love again, and online dating might feel like a big unknown ocean that you’d rather not dip your toe into. Dating can look both daunting and like no fun at all.

 The truth is—and I’ve seen it over and over again with hundreds of clients—that getting back into the dating world can not only be enjoyable and life-affirming, it can also expand your circle of friends and introduce you to that one person you want to spend much more time with.

 Finding a relationship is also good for your health. There are numerous studies that show that people in serious relationships have fewer health problems and live longer. In my own work, I’ve found that those positive results start even before my clients have found a partner. Just by beginning the process of looking for a relationship and expressing their desire to make a connection with a partner, many of my clients start to get over their depression, fear, and sadness. While they start out feeling vulnerable, taking care of themselves and opening themselves to the possibility of finding love makes them healthier and happier.  Dr. George Vaillant, who led a longitudinal study that followed 268 Harvard graduates over seventy-five years, says that there are two pillars of happiness. “One is love. The other is finding a way of coping with life that does not push love away.”[i] I emphasize with my clients how important it is to stay open to love, both while they are looking for it and once they’ve found it.

 The following seven tips will help you own your Valentine's Day.

 1.  Embrace a positive perspective

Creating the right mindset is so important to entering the dating world. Fear and doubt will affect your results, as will going into it with an open mind, confidence in who you are, a strong sense of what you are looking for, and patience. A positive mindset will help you attract people you want to be with.

When you think and talk about dating, use words that build you up rather than defeat you before you’ve even started. For instance, instead of saying, “I’m old and men/women want to date people younger than me,” say “I’m a beautiful person, and would make a great partner.” Those words might not immediately change what happens externally, but they shift your perception of the experience and create a more positive atmosphere around you—which is always attractive.

 2.  Identify who you are and what you want in a partner

Begin by answering a series of questions that clarify where you are in your life so that you can look for and attract the right person for who you are today. We don’t always recognize the ways in which we’ve changed over the years until we slow down and take an honest look at the answers to some basic questions. Questions like: Would I date myself? Why, or why not? What are my best qualities? What would I like to change about myself? What kind of relationship am I looking for right now? What has worked for me in past relationships and what has not? Why? What can I learn from what past partners have said to me about our relationships?

Write down the answers to those questions and keep them somewhere where you can find them. When you are feeling uncertain about how things are going in your dating process, and why they are going the way they are, this list can be a helpful resource. And your answers will change over time! As you become more confident in the dating world, you will add positive traits to the list. The type of relationship you are looking for might change based on the people you meet. But use the list to remember who you are and what you want.

 3.  Enjoy the process, don’t just focus on the outcome

It’s easy to get fixated on the outcome of any process, and dating is no exception. You want the joy of meeting that special someone, not necessarily the effort it takes to get there. But as with anything worth having in life, the process is critical and you might as well enjoy it, because much of it is actually a lot of fun.

 What does enjoying the dating process look like? Opening yourself to the self-growth that dating can offer. Getting excited about the people you might meet, and would not meet if you weren’t doing this. Broadening your social circle (who doesn’t need that?). Learning about yourself and growing in unexpected ways. Exposing yourself to new worlds through the people you’ll meet. Letting go of the pressure to find “The One” or the feeling that you have no idea what you are doing. Convincing yourself that this will be fun.

 4.  Get online

While technology is completely integrated into our daily lives, online dating can still seem strange and intimidating. As someone who began her career in traditional matchmaking and now works online with the majority of her clients, I can tell you that it is totally manageable, safe and very exciting. With online dating, the pool of prospects that would be out there in traditional matchmaking or your daily life grows to an ocean, and many of the people on those sites are absolutely the type you want to meet. Over the years I have found many ways to optimize my clients’ experiences with online dating. 

Still not sure how you feel about going online? I hear a lot of myths about online dating from my clients, and I want to dispel the most common ones.

 The first myth is, “The type of person I want to meet is not on online dating sites.” Truth: I began researching online dating in 2008 as a way to help the clients I was working with then, and I can assure you that consistently over the years there have been thousands of quality men and women over fifty on online dating sites. They go there for the same reasons you will: they are successful, motivated, and intelligent, and they realize that this is a fantastic way to meet people.

 The second myth that I hear is “I’ll look desperate.” Truth: being motivated and proactive is hardly desperate. I always ask my clients, when they are out with a friend and see someone attractive, do they hide? No. There’s no shame in desiring companionship.

 The third myth from clients is that their professional reputation will be ruined if they are on online dating sites. If this feels like a legitimate concern for your particular profession or company, take advantage of the ways to limit your visibility by using privacy options which most online dating sites have.  You can also verify the legitimacy of people who express interest in you through the almost unlimited information available online. Remember, desiring companionship is natural, and online dating has become very accepted as a way to find relationships.

 5.  Be methodical about the dating process

This probably sounds a little rigid—isn’t dating about the freedom of meeting people and having fun? Well, yes. And no. Back in our earlier years, our relatively unfettered lives allowed us all sorts of opportunities to meet people: through friends, work, and shared activities. The possibilities seemed endless. But once we settled down, bought a house, had children, and established a career, our circles often got smaller. If you look at the people you know today or are likely to meet in your everyday life, chances are that many fewer of them are single than you’d like if you’re laying odds for finding someone.

 Establish a plan with defined steps along the way, and change course when something isn’t working. Being methodical doesn’t mean getting stuck—it just means providing yourself with a roadmap that keeps you from getting lost along the way.                

 6.  Maintain a marathon mindset: optimism and resilience

Optimism is so important when you are dating, because things don’t happen in a linear way. You will meet people you are not interested in or who are not interested in you. Sometimes it takes a while to find someone you want to see more than once. You will meet someone interesting and date for a while, but then it won’t work out. All normal! And those times will alternate with times where you meet many interesting people, go out on fun date after fun date, get a lot of positive feedback, and eventually meet someone for the long-term.

The bottom line is that it won’t always be easy or predictable, but you can’t give up at mile 11, and you can’t let adversity keep you from trying again.

 7.  Know what to do if burnout sets in

Finding the right person can take time, and sometimes burnout will set in. If this happens, don’t give up! Try adjusting your expectations. For instance, if you are expecting to meet “The One” fairly quickly, why not give yourself a chance to go out on a few dates with people who sound interesting even if they do not seem to be your ideal? You might be amazed to find out you like them more than you thought. And you’ll have more fun along the way.

 Burnout is essentially disappointment, and we all experience that from time to time, so don’t be hard on yourself if you get there. Remind yourself of where you are in your life and keep focused on the type of person for you. However, don’t narrow your focus so severely that you miss out on other possibilities around you, from meeting other people to trying new activities. Remember to enjoy the process! You can believe in a positive outcome without knowing specifically what that will mean for you.

 You can also always take a break for a while. Dating is not a speed contest, and taking the time to take care of yourself and having the patience to find the person who is right for you is the most important thing you can do.

I really appreciate that re-entering the dating world is not easy. You are taking an emotional risk, and putting yourself out there in a way that feels very vulnerable and exposed. But give yourself kudos for even considering it, and now that another Valentine’s Day is upon us, use this moment to begin an exciting new adventure (quite possibly your best yet)—the process of finding a Valentine.