Lessons from a Hundred Heartbreaks

Dating has to go wrong before it goes right.

Photo by NeONBRAND on Unsplash

Most people stop going to bars after they get married. Have you noticed? In our 20s, we love going out. We’re so happy to pay ten times normal retail price for alcohol.

Why? Because we’re all trying to find someone. We’ll do anything to achieve that. Once, I stayed out until 4 am with an ex and drank seven beers until we finally went home and sorta had sex.

Sorta means it came out, but never really went in.

Probably thanks to too many drinks. Sorta sex can happen a lot in your 20s, especially if your life resembles a dumpster fire.

My ex and I had a great few days. We were back in love. Then we went on a romantic walk around campus, sat down in a little garden area, made out for a few minutes, then he dumped me.

“You’re just not the one I’m looking for,” he said. “But trust me, you’re going to find someone great.”

Dammit, I’d put almost a hundred dollars worth of dutch dates on my credit card this relationship. Drinks, a movie, a play, more drinks. It adds up. Now I was back to square one.

I’d love to say I was just looking in the wrong place, but I wasn’t. We didn’t actually meet in a bar. We met in one of my Englishes classes. On the surface, we matched perfectly.

But I wasn’t done growing. Neither was he. That’s the real reason we didn’t last more than a couple of weeks at a time.


You might see your 20s as a string of failed relationships. But maybe they’re not. Like friendship, romance can blow through like a thunderstorm. Each one leaves you a little wiser and more self-aware.

We think and talk about dating in strange ways. Someone dumps you. Or you dump them. Our friends hug us and say we’re too good for them. “They don’t know what they’re missing.”

But they kinda do know.

Sure, we can demonize our exes. Some of them deserve it. But really, there’s no point. Doing that blinds us to bigger lessons.

Most importantly, we learn more about what we want, and what we need. We learn what we can offer someone. And we also figure out a little bit more about how to bring the two into alignment.

One of my biggest heartbreaks happened at the age of 24. A theater actor hit on me in a cafe. He offered me tickets to a play he was performing in. We stripped on our first date.

The attraction was intense. That said, we lasted about two months. It wasn’t just that our personalities failed to match. Years later, Facebook would tell me he married my practical doppelganger.

The problem was I tried to turn myself into his mirror mate. The mirror mate pretends to love all the same things you do. They try to think and act the exact same way as the person they’re dating.

Mirror mates don’t make good longterm partners.

My actor boyfriend loved the spotlight. And I was a bookish wallflower. At the time, I didn’t accept my nature. So I tried to impress him by faking extroversion. Huge mistake.

Once, I even tried to tell a funny story at a party in front of all his friends. None of them laughed.

A few days later, we broke up.

Okay, fine. He dumped me. That weekend was painful. My brain played imaginary conversations between him and his friends, about how he could do better — someone who could tell hilarious stories at parties.

Truth: I’d fucked up the relationship by not understanding myself. It’s completely possible that he liked me exactly because I was more reserved, a complement to his extrovert phenotype.

We’ll never know, because I tried too hard.


My later 20s brought about a definitive change in my dating habits. Finally, I stopped giving a shit what my dates thought.

It’s easy to fake a personality to attract dates. Pickup artists throw that advice around like candy.

If you just want dates, the pickup persona works wonders. Sure, you’ll probably score a lot of phone numbers.

You might even be able to get away with lines like, “Suuup, girrrl?” Even so, you’re probably not headed into a stable relationship.

The biggest cliche in the world turns out legit. Just be yourself. But that’s not so easy. First, you have to figure out who the hell you are. Second, you have to act like that person despite certain instincts.

It turns out that being yourself takes a lot of practice. Especially on a hot date that’s not going so well.

Being yourself might mean you forfeit your hot date.

That happened to me a while back, after my fiance and I split. At a teachers’ conference, I met quite possibly the most perfect man alive. He checked all my boxes. He even had the same name as my current partner.

In fact, he could be my current partner’s brother.

We eyed each other for an hour, all while forcing our CVs into the hands of school principals. That’s right, I was slumming at a high school teachers’ job conference, and also flirting. Not professional. What of it?

At lunch, he introduced himself. We wound up grabbing coffee for two hours. At the end, he hugged me. And I kissed his cheek.

Unfortunately, he lived six hours away.

We made plans for a proper date a few days later. But I couldn’t follow through. Still raw from an imploded engagement, weak from months of job hunting, the last thing I wanted to do was hop in my car on a Friday afternoon and empty my gas tank for a date.

Here was a moment of self-awareness. The early 20s me wanted to push through. Force myself across time and space to meet with the man of my dreams. Late 20s me needed to crash hard.

“Life’s all about risks,” I thought to myself.

But a dehydration headache was kicking in. I’d taught three classes that day, and was coming off an all-nighter from the other day.

So I cancelled the date.

And the man of my dreams ghosted me.

The very next day, I got my first job offer. Nothing tenure-track. Just a silly one-year VAP. But it was the beginning of my career.

Serendipity? I’ll always wonder.

Part of me knows how that date would’ve gone. I would’ve shown up exhausted, barely able to speak. The sparks we’d felt earlier would’ve smothered themselves. Nobody in their right mind would’ve kissed me that night — an exhausted, tattery grad student.

When they say be yourself, nobody tells you that doing that really sucks. Sometimes, it means admitting to yourself that you’re in no shape to drive six hours for a date. Even for the man of your dreams. Our insatiable desire for connection drives us to hurt ourselves. But if you really want connection, you’ve got to put yourself first, even if it means giving up.


Desperation for connection even propels us against our most basic common sense. A friend of mine asked me a strange question a few years ago. She was striking out on the dating apps. Finally, she met someone who didn’t run out of conversation before the food came. “There’s just one problem,” she said. “When he hugged me, I cringed.”

I said, “So you’re not attracted to him?”

My friend shook her head violently. “I feel so bad,” she said. “He physically repulses me…Should I keep dating him?”

His profile photo didn’t look bad. It wasn’t a matter of looks, but chemistry. They just didn’t match up.

After I said no, my friend went on three more dates with the poor guy before ending it. She was trying to let him down gently, she said. But in truth she was acting cowardly, and a little selfish.

I’ve made the same stupid mistakes. A while back, I also dated someone who didn’t turn me on — not even a little. But he was interested in me. He looked good on paper. Plus, he asked me out. I couldn’t think of a good reason to say no. So we dated for two or three weeks.

We even kissed a few times. Then I ghosted him. Like my friend, my decision showed a lot of cowardice and cruelty.


The best thing I ever did was spend a year single. It was semi-intentional. After dumping a longterm boyfriend, I dove into my dissertation.

There was no luxury for distraction. If I wasn’t working, I was sleeping or watching Netflix in a restful, vegetative state.

Weekends rolled around. Instead of heading to the bars, I slept for 10 hours on Friday night and then holed up in my apartment for marathon writing sessions. Then I graded papers.

It was kinda beautiful.

That time wasn’t just about my dissertation. In the spaces between work, there was a decent amount of space for reflection.

Turns out, I’d cut corners on my growth as a human being.

At the end of that year, I met someone — not all that different from the hundred guys I’d dated before. But this time, I felt a certain kind of peace and stability. Maybe I finally knew what I was all about.

At one point, I’d looked out across the open range of my life and looked forward to decades of bachelorette-hood. The prospect of spending the rest of my life single actually felt possible, even great.

Then I met someone. That was the relationship that stuck.

Coincidence? I’m thinking no.

You’ll hear a watered-down version of this advice. If you want love, you have to love yourself.

But what does that mean? In concrete reality, you have to actually like the idea of spending the rest of your life alone. No boyfriend or girlfriend. No dates. No bullshit. If that sounds kinda nice, then you’ve achieved something. Maybe you don’t have to love yourself, or like yourself, but you can get along with yourself just fine.

I’ve noticed that people are attracted to this attitude. They can see it in your body language, in your bones. And you can’t fake it. You have to be okay with a life by yourself. Because you have more to contribute to the world than candlelight dinners and babies.