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How My Worst Date Turned Into One Of My Best Friendships

It doesn't have to be *all* bad.

It started out kind of cute. I was playing an acoustic open mic night in some hip downtown bar, when I saw Jim’s* name on the set list. I noted that I had never met him, even though I had been playing that open mic for a few weeks. So, when the host called him to the stage, I scanned the crowd to put a face to the unfamiliar name.


From the shadowy corner emerged a guy with big soulful eyes and a jawline that could cut glass. But it wasn’t until he got on stage that I knew I had to talk to him. Glowing in the spotlight, he proceeded to play the most poetic original songs, with impressive musical technicality and a charm that melted all my defenses. Unfortunately for me, as soon as his set was over, the host called my name. From the stage, I could see Jim packing his gear. And before my first song even started, he had left the building.

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Naturally, I went home and obsessively searched for his social media profile. When I found it, I slid into his DMs. To my relief, he quickly responded, saying that he was sorry he had to miss my set, but that he noticed me too and wanted to take me out on a proper date!

On the night of the date, I glammed myself up. He picked me up at 7 p.m. in an impressive vintage BMW, and I was ready for whatever fancy dinner he had planned.

But then he drove to...Starbucks.

I mean, it wasn’t bad. I guess I wasn’t super hungry. And who doesn’t like coffee, right? We ordered our lattes and sat outside in the cool summer breeze. Night fell and the stars twinkled above us as we sat across from each other for one hour, then two, then three, then almost four.

It could have been a nice date—if he hadn’t spent the entire time talking about his ex-girlfriend. If she was as boring as he kept insisting she was, I’m not sure why he thought she would be a good topic of conversation. I learned about her hair, her body, her job, her favorite bands, her insecurities. By the end, I felt like I was on a date with her!

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It didn’t help that drinking coffee on an empty stomach put me on a wave of mild to epic restlessness, that eventually crashed hard. Because, while it’s not a bad idea to bring up past relationships with new romantic prospects, a good date rarely includes all the gory details of how a former sexual partner failed to satisfy.

It could have been a nice date—if he hadn’t spent the entire time talking about his ex-girlfriend. 

Beyond being mind-numbingly bored, I was annoyed that he tacitly wanted me to live up to what his ex-girlfriend couldn’t be. It didn’t seem like he could see me sitting across from him, let alone care to get to know me. I remember the distinct feeling that I was a just vessel for him to place all his expectations into. And I knew that if I couldn’t live up to the fantasy—he’d get rid of me and complain about it all to his next date. As quick as the crush began, I was over it.

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While it helped that he was nice to look at, I can’t believe I was polite enough to sit through all that. Still, I’m really glad I did.

After the date, Jim made a move, which I had to turn down. And instead of being offended or awkward, he took it in stride. In fact, getting it out of the way seemed to lift the tension. The mood shifted. It was as if the performance was over, and now we could finally be ourselves. And for the first time that evening, we started to really see each other. He was no longer the jerk trying to build a fantasy girlfriend, and I wasn’t a blank to be filled (or whatever he thought I was).

With a new wave of energy, we decided not to part ways just yet. The date turned into a hangout, and we spent another hour or so driving around, listening to music, until we found a lakeside parking spot. Jim popped the trunk, pulled his guitar out, and played some tunes as we talked about everything from what classes I was taking that semester, to his travels through Europe, to friend and family drama, to our struggles with mental health issues.

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The mood shifted. It was as if the performance was over, and now we could finally be ourselves. And for the first time that evening, we started to really see each other.

We never went on a second date. But after genuinely bonding, we continued to talk and hang out regularly—even when we both got into relationships. Now, eleven years later, we are among each other’s closest confidants. When he was diagnosed with a terminal illness, I was one of the few people he opened up to. When I was in the throes of a dark depression, his friendship was a source of true comfort for me. Our relationship is so solid that it’s hard to believe it started off as a weird date.


Looking back, I realize that the guy I sat across from at Starbucks wasn’t some gross, entitled person trying to undermine my individuality. He was just a nervous, rambling boy. And sure, a lot of bad dates deserve to be thrown in the trash. But sometimes, what’s unappealing from one perspective is a stroke of luck from another.

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