The Dating Advice I *Wish* Someone Had Given Me in My 20s

The worst breakup of my life turned into the most important lesson I ever could have learned.

When I was 24, I met the guy I thought I was going to marry.

After two great dates, we booked a romantic vacation to Mexico over New Years—not to toot my own horn, but this was 2015, right before "going to Tulum" became such a cliche that it lost all its magic—and the rest was sort of history. He was with me when my dad died, when I started my career as a writer, and when I decided to ditch my life in New York to travel around the world.

At the time, I thought I was head over heels in love with him. I said all kinds of cliche things to my friends like, "This is it!" and "When you know you know!" ” Excuse me while I cringe.

After a year and a half, the relationship ended while I was on a comedown from a Bulgarian rave, which is a story for another time (though what I will say for now is: 10/10 would not recommend). It's not worth getting into the details of what turned out to be one of the most painful breakups of my life (and not just because the teary conversations were regularly interrupted by me running to the bathroom to throw up Bulgarian vodka), but it basically boiled down to the fact that I had been through an immense amount of trauma when my dad died—I mean, I literally fled the country—and wasn't mature enough to realize that he wasn't the right person to give me the support I needed.

I flew home and spent two weeks nursing my heartbreak at my mom's house, then returned to the rest of my year abroad to find the version of myself I'd been looking for when I ran away from home in the first place.

I spent the next six months going on dates with gorgeous South American men who smoked hand-rolled cigarettes, riding around on the back of a guy's motorcycle, and staying out until sunrise sipping pisco sours.  I went from assuming that settling down and moving to the suburbs (maybe in Texas?!) was the logical next step to rebelling against that lifestyle in every way I could possibly think of.

2017 was a whole-ass vibe.

It was around this time that all of my friends started getting engaged and married, and when I returned to New York after nearly two years of drinking (and dating) my way around the world, I felt more isolated than I ever had in my life. Finding "the one" had been my lifelong goal since I fell in love with Gerald Kaplan during Kindergarten nap time, and at age 26, I felt like a complete failure. I was so painfully alone that at times—like when my friends and their new fiancés went on double and triple dates that I wasn't invited to, or when I trudged home from the bar by myself after dozens of failed flirtations—it physically hurt.

I realized I may not ever be able to find my soulmate (which is a ridiculous way to feel at any time, but especially when you're in your 20s and decades away from having to worry about dying alone) and decided it was up to me to find other ways to make myself happy. I shifted the focus of my nights out away from tracking down a husband (which, let's be honest, was never going to happen at Hair of the Dog or Sidebar) and toward spending meaningful, fun time with my friends,  I threw myself into work and found success doing something I genuinely loved, and I took myself on dates and romanticized even the most mundane parts of my life long before TikTok made it a #thing.

I decided to just... do me, and spent three magical years getting to know myself in a way that I never would have been able to if the guy I'd fallen in love with at 24 turned out to be the one. I lived every moment to the absolute fullest, and instead of obsessing about finding someone to make me happy, the way society had convinced me I was supposed to, I created happiness for myself.

Even now, in the year of our lord Barbie, so much of our self-worth as women is tied to our ability to find someone to love us. Research has shown that women, more so than men, tie their opinions of themselves to being in a relationship—a fact that makes me cringe, but also nod my head in agreement because I've been there. And if I hadn't gotten the chance to fall in love with myself, I probably still would be.

When I finally did meet the man I've deemed worthy of fathering my toy poodle I'm going to marry, I wasn't even looking for him. At that point, I had found my happiness and become the fully formed version of who I wanted to be, and I didn't want to sacrifice a single part of that for someone else—something I'd been guilty of doing in every other relationship I'd ever been in. I was always too much or too loud or too sparkly, and felt like I needed to make myself smaller to be worthy of love. But after falling so deeply in love with every part of myself (... which is SUCH a Lisa Barlow thing to say), I realized that I didn't want anything to do with anyone who didn't feel the same way.

I was so focused on doing me that when my husband-to-be drove into my life in a beat-up Jeep Wrangler, I didn't really care. I didn't waste my energy trying to impress him by being a sanitized, more palatable version of myself—on those first few dates, I let my damn freak flag fly. And much to my surprise, we fell in love. Not in spite of how wholeheartedly myself I was (so, an all-out weirdo), but because of it.

There is so much pressure associated with finding the one before you're past your prime (WHICH ISN'T A REAL THING), and not nearly enough conversation around just how important it is to find yourself. I've watched so many amazing women in my life beat themselves up after bad dates and failed relationships, largely in fear that they missed their shot at a happily ever after. And if there's one thing I could say to any of them—and to my 24-year-old self—it's that loving yourself has gotta come first. When you take the time to do that, the rest will come... but it won't matter nearly as much.