The SW Experts | Startup Dating
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Startup Dating

Startup Dating


As a journalist, one of my beats is covering female tech entrepreneurs with startups. I regularly sit down with these women to hear their stories. Many have exciting and fulfilling careers looking for and developing the next great thing – and they know when it’s time to move on.

I got to thinking that my dating history is pretty closely aligned to the startup world (when I actually make it to the launch.)

These days, when we typically meet online while at home in our pajamas or swiping through an app while waiting in line for the morning coffee, there’s this limitless supply of potential suitors. (Well, maybe not limitless, as some apps let you know when you’ve temporarily exhausted all possibilities in your geographic area who fit your desired demographic!)

It’s pretty easy to get into the pattern of dismissing those who might not fit all our qualifiers on paper – or to wonder if there’s someone out there who might be a better fit.

Even in the days predating Match, Tinder, et al., I’m not sure I ever was the settle-down type. What I’ve always liked best about dating is the opportunity to meet new people. I’ve never been the type to stick with one group to the exclusion of everyone else.

When I was in elementary school, I was the girl who became BFFs with The New Kid and one of the things I love about my work is that I get to speak with all kinds of fascinating people who are passionate about their fields.

I love first dates and the “what if’s,” that moment when you contemplate the potential. Sometimes that leads a second date, perhaps a few months of dates, or even a friendship. But, on the flip side, dating today often means one party or the other will eventually move on. Startup dating can be pretty compelling.

We’ve all read enough advice from dating gurus and listened to enough webinars and podcasts that advise women when a ring doesn’t appear in the remote future to cut our losses and find someone with matrimonial goals. But what if we aren’t sure we want to step down that aisle?

Still, lots of us who have spent time single have those moments when we wonder if there’s something wrong with us. We read dozens of articles and self-help books that tell us if we would only lose ten pounds, change our hairstyle, stop wearing mom jeans,  get a job at a  Tesla dealership, hang out at a shooting range or move to Alaska, we’d meet The One and live happily ever after.

[Tweet “I’ve come to realize that life isn’t a one size fits all proposition”]
Last year, I fell down that rabbit hole of obsessing over what I could change to turn around my seeming inability to attract men who wanted a long term relationship and decided to speak with a therapist. During one of our first sessions, the therapist asked, “What will happen if you don’t meet The One?” At first, I was taken aback. Was she saying I wasn’t good enough?

I paused a moment and answered, “Nothing. Nothing will happen. My life will still be interesting. I’ll continue to meet fascinating people and have a wonderful relationship with my kids.”

The therapist replied, “If you wanted to be in a long term relationship, you would be. There’s nothing wrong with independence if you embrace it.”

That was a major turning point for me. I stopped blaming myself or thinking maybe I wasn’t good enough and realized I like my life just as it is. That doesn’t mean I’m closed to the idea of pairing with someone great but I am aware my plate is pretty full. My kids and my lifework come first.

Sure, there are times when, like many single or unmarried people, I wonder what my life would have looked like if I had remained married to the father of my children, if we had been good complements to each other. I’ve come to realize that life isn’t a one size fits all proposition. Some people are happily married; others are not. Some people will move on to a new mate. Others will be happy with a life surrounded by friends and occasional dates.

There’s no single path that makes every one of us happy. As long as we accept what we truly want and not what others prescribe, we can be fulfilled.

So, I’m continuing my journey as a startup dater! (At least for the time being!)