What I Wish I'd Known Before I Got Back Into The Dating Scene

Fifteen years ago, I met a boy in a nightclub. He bought me a drink. I wrote down my number on a business card, and the rest is—as they say—history. We dated; we fell in love. We got married, bought a house, and had kids. We were happy. And then he got sick, and we fought for his life, and we failed. He died.

Instead of happily ever after, I was left to pick up the pieces of our shattered dreams and parent our grieving children alone. I did so—first by just going through the motions, and then because I found that I could. I found that it was possible to rebuild dreams and solo parent while also navigating the maelstrom of grief that ebbs and flows with no rhyme or reason. It was around then—when I saw how life and loss coexisted in every moment—that I considered online dating.

The last time I was in the dating world, online dating was barely in its infancy. This time around, online dating is (or seems to be) the foundation of modern dating. And I wish I could say I approached dating post loss, or dating the second time around, thoughtfully. I wish I could report back and promise that I thought through…well, any part of it, really. But I didn’t. Aside from implementing the safety advice I’d gleaned from widows’ groups, the moment a friend suggested I give dating a try, I dove in—blindly and foolishly—spurred by loneliness and something else I can’t quite name. That very night, I downloaded Bumble, created a profile, panicked, deleted it, and then downloaded it again. I started swiping, and realized I didn’t just not understand online dating, but I didn’t understand dating at all.

For the two years prior to joining Bumble, I’d been immersed exclusively in the cancer caregiver world. For the five years before that, I was preoccupied in the parent of young children world. I was so far removed from pop culture and trends that I spent half the time Googling words and acronyms on profiles and the other half trying to remember if swiping left was a yes or a no.

It’s been a while since those earliest, very confusing days, and I am by no means (not any at all) an expert on dating the second time around. In fact, I’m fairly sure your best bet is to do the opposite of my advice. But I’ve been exposed to the second-time-around dating scene long enough now to know what I wish I’d known those first naïve days.

I wish I’d known not to take ghosting personally.

Well, actually, first I wish I’d known what ghosting was, but once I got that concept down, I wish I’d known that being ghosted, especially by a match after a few back-and-forth messages, is less a rejection and more a testament to the other person’s own issues.

I wish I’d known how easy it is to let your self-esteem hinge on a stranger’s swipe, and how detrimental it could be.

I wish I had been more careful about equating my worth as a person and a potential partner to the number of matches I had.

I wish I’d known not to be afraid of anyone’s judgment.

I wish I hadn’t hidden the fact that I was entering the dating world and panicked whenever I saw a familiar face on the app. There’s no shame in seeking companionship. There’s no shame in hoping there’s something worth putting yourself out there for on the other side of a shattered happily ever after.

I wish I’d known I wouldn’t find the man I had married in the profiles on any app.

Logically, I knew I wouldn’t. He’d died and the chance that Matt 2.0—a near exact match of his humor and heart—was just waiting to be swiped on was hovering around zero. And yet, in those earliest days, I swiped no (that’s left, I think?) on a potential match and even ghosted a few conversations (like I said: ghosting is a testament to the other person’s issues) simply because he wasn’t Matt. If I take a step back, I think that all amounts to wishing I’d taken the time to figure out exactly what I wanted in my life 2.0, before I dove into trying to create it.

I wish I’d known to be a little more cautious with my heart once I did match.

With each match, my heart soared too high. Each time I found myself exchanging messages and smiling at my screen, I began to dream. I wish I’d known to be realistic. But then, also, I’m glad I didn’t know. I’m glad that I found, when left to its own devices, my brain was certain it was capable of loving both a man I’d lost and a man who would one day come into my life. I’m glad I found that in my core I still believed—maybe not in happily ever after—but in something approaching that.

I wish I’d known it could be fun.

Stressful and discouraging and bewildering most of the time, for sure, but also fun. Fun to chat and to meet people who you might never meet in normal life. Fun to hear stories and learn the way someone else sees the world.

Mostly, I wish early on I’d known to be gentle with myself.

I wish I’d known—and should have guessed—that I would make a thousand mistakes a thousand times over and that sometimes life happens in the moments when you were waiting to know better—and also remembered which way to swipe for yes and no.