In our swipe-right culture, dating has become gamified. And this is GREAT when you aren’t sure what you’re looking for (except for fun, that is), and are still preoccupied with your career.
But at a certain point you may find you’re ready to find a longterm partner. Unfortunately, if you’ve been in a demanding professional environment for a few years you might not feel 100% comfortable moving into more serious dating.
Here are a few of my recommendations to help you feel more at ease as you start looking for that lifelong connection.
1. Commit to Growth
A surprising secret is that dating is a skill, just like anything else.
Think about it. You’re successful in your career because you’ve put an extensive amount of time, resources, and energy into developing yourself professionally. You’ve nurtured your skills, taken risks, and invested countless hours of effort.
Have you done that with your dating life? I suspect not. 😉
You also didn’t anticipate being at 100% in your career from day one, when you started your path to success in work. Instead, you allowed yourself a few missteps along the way. You embraced the fact that there’s a learning curve in every profession.
Serious dating is very much the same. It can feel awkward at first. Really awkward.
Especially if you’re used to being in charge and tend to feel best about yourself while working, innovating, or dealmaking. (I see this often, especially with the highly-successful men I work with as a luxury matchmaker. They get into that leadership zone at the top of their game and feel great in that particular role, so naturally they want to spend a lot of time there. That’s not so great for dating.)
The same level of mastery and ease you have as a professional can happen with dating—IF—you make an investment, and push through the occasionally less-than-ideal moments.
In other words: Don’t let a little discomfort drive you back behind your desk or the safety of a screen. If you do that, you’ll never grow into the romantic leading role that delivers the worthwhile connection you ultimately want.
Instead, smile at yourself and accept that risk and awkwardness are part of the process. See the humanity in the situation, embrace it, and even have fun with it. Your date is feeling awkward too!
Remember, dating is a skill. The more you do it, the better you get at it. And the better you get at it, the more enjoyable and rewarding it is!
2. Leverage Your Networks
While every dating app has it’s place, don’t overlook the power of exponential connection to bring you into the orbit of your future other-half. The same way you might call on your professional network to source and recruit an outstanding new CTO or stellar in-house counsel, you can low-key put the word out that you’re single…
Now, I’m not saying you should publish a post about it on LinkedIn. But I am saying it’s worth it to drop a hint here and there when you’re in casual conversation with other professionals—especially those in a position to introduce you other like-minded individuals.
After all, the singles in your extended circles are most likely to share your interests and social status.
Your professional network isn’t the only one to tap. Family, friends, social clubs, country clubs, sporting leagues, and philanthropic networks are also worthy opportunities. There is a reason that introductions have been a traditional way of pairing off through the ages.
All of us have been single at one time or another, including your colleagues, clients, and peers. So mention it.
It’s quite possible you are just one or two degrees removed from a person you’ll want to spend the rest of your life with.
3. Start with Coffee
First dates should be short! (And fun!)
Knowing that the date is going to last just three-quarters of an hour allows a lot of the pressure to evaporate. Ask a few questions, answer a few questions. Everyone gets a chance to learn and a chance to share.
But juuuusst enough for everyone to know whether there should be a second date.
4. Be Warm and Engaging
Do not prepare a list of interview questions you will ask your date. Do not plan to drop names of tech celebrities you know or titles of roles you’ve held.
Although you are a success, dates are not about anyone’s resume.
Be prepared to talk about things you know you both share an interest in (traveling, philanthropy, music, Esalen, golf, basketball), and also prepare to be good company.
Ask questions that don’t require a yes or no answer, such as “How did you find yourself living in such an exciting city?”
Being authentic and open, with genuine interest, is the key here. (I know I don’t need to tell you where your phone should be during all this.)
5. Text a Thank You
The old adage about waiting three days after a date to make contact is no longer. The same way you would thank a VC for feedback on your pitch-deck or slack a quick gif to a colleague after a meeting, it’s fine to send a brief text acknowledging that you just spent time with someone and enjoyed it.
Leave the gamification to digital dating, so that your real life sensibilities can take over at this stage of your personal life. Something as simple as “Hey, that was fun. I’d be willing to do it again,” or “Thanks—really enjoyed it!” is fine.
I love talking about this and could go on forever with everything I want people to know about how easy it can be to find and connect with the right person.
When you are caught up in your professional life, genuine romance can be elusive. If you’re not quite ready for a professional matchmaker, embracing a few simple behaviors and engaging in a little bit of practice can ultimately have a very positive impact on your personal life.