Remember that one date with the “method actor” who didn’t believe in tipping? The one with the stand-up comedian who insisted on recording your back-and-forth for material? The one where your counterpart arrived 27 minutes late, wearing just one flip-flop? Naturally, the list goes on.
But here’s a hot take: These dates, albeit “unsuccessful,” have their merit, too. Whether we’re pursuing eternal love, great sex, or solid banter over negronis, our sub-par dates can be just as formative as our objectively good ones. And there’s a case to be made for celebrating them for all their influence. Maybe you discovered a new favorite restaurant, learned to pronounce “amuse-bouche” correctly, found out that orange wine is not actually made with oranges. Perhaps you made a solid, platonic friend. Inevitably, you whittled away at what you are (and aren’t) looking for in a partner — which is profoundly valuable, even when it doesn’t conclude with a wedding hashtag.
So, in the interest of imbuing our imperfect romantic encounters with a little added joie de vivre, we reached out to 10 modern daters about their most memorable meetups and the unexpected takeaways that came in tow — among them, a Bumble devotee networking her way to her first book deal, a woman re-learning her sexual preferences, and a serial dater coming to terms with his cat allergy. Read ahead, and see if their stories help you reassess your definition of a “bad date.”
“I generally date in pursuit of a relationship, so I can be a little stringent about my prospects — and judging by his app profile, this particular man was not my type. He was objectively sloppy, between jobs, and presumably too busy for complete sentences. All the same, something about him appealed to me. So, with two hours notice — that’s this guy’s M.O. — I somehow found myself on a barstool next to him, totally leaned in, one night after work.
“He told me how he’d just left his desk job and purchased a one-way ticket to Central America. He was going alone with plans only to learn to surf and meet people. A real adventure. I like to think I’m all about authentic travel, but without fail, my trips feature a reliable friend and an embarrassingly detailed itinerary. Of course I wasn’t going to end up with this guy — he wasn’t looking for anything serious in any aspect of his life — but the date was enough to convince me that a little instability might be good for me…at least in my next adventure.”
“I once went on a first date with someone who told me he didn’t vote in the 2016 election. I left immediately — it was the shortest date I’ve ever been on. But on the flip side, it underscored the fact that this was a true non-negotiable for me in a partner.
“Now, I tend to tell that very story as an icebreaker on most of my first app dates. It gives me the perfect segue to ask someone about the last time they voted and if their registration is up to date.”
“When I travel, I use dating apps to meet people in new places. Once, while in Vancouver, I matched with someone on Bumble who worked nearby, and was up for having lunch. I don’t normally match with guys 6’4” or taller (I’m only 5’3”), or guys below 35 (I’m in my mid 40’s). This guy was 6’4″ and in his early 30s…but it was ‘just lunch,’ so I agreed to go. And we actually had a fantastic conversation. We talked politics and careers and general life stuff.
“After we said goodbye, I realized something important: None of my standard dating app ‘deal breakers’ were written in stone. People can always surprise you, if you allow them to do so. I’d had a lovely time with someone who didn’t fit my normal criteria. It was a real eye-opener.
“Now, I’ve been using Bumble for a few years, and I sometimes wonder if I should delete it and put myself out there in other ways. But part of me feels like, if I did, I would be losing this portal…to possibilities, future connections, and genuine human laughter. In a way, I’ve made peace with the fact this app isn’t necessarily the place where I’ll meet a long-term partner, but in an increasingly disconnected world, it introduces me to people I wouldn’t normally meet. And for that I’m grateful.”
“After SEVERAL dates with this one guy I met through an app, we decided we had no real chemistry. We hadn’t had sex; neither of us really seemed to want to. It was a strange in-between. But in figuring out our next steps, we came to the conclusion that we got along great. We just weren’t well-matched romantically. Now, he’s one of my closest friends. He actually just came over last night to watch a movie with me and my roommates.”
“Last year, my boyfriend of two years and I broke up, so I downloaded dating apps to ‘bounce back.’ My ex and I had a really consistent sex life. Like, a routine. Nothing changed much. Then, this new guy — who I never saw again, by the way — came home with me after our first date. When we slept together, he asked me all these questions about what I wanted, what I liked, what I didn’t like. I know this sounds insane, but in literally two years of dating someone, I really hadn’t been asked those questions.
“It caused this whole spiral for me: I didn’t know what I wanted sexually — or how to ask for it. And I was an adult woman. This one dude was the reason I was like, Priya, it’s your job to figure this out. You need to know your own preferences sexually, and you need to advocate for them. I have him to thank for that. Though I’m not actually sure I remember his name…”
“I started doing the dating app thing earlier this year, purely out of loneliness. I talked to a bunch of people, but I wasn’t coming across many who excited me enough to actually wanna meet up with them. Finally, I made myself, because I felt like it was what I was supposed to be doing. But then, after like 20 minutes at drinks with this guy, I was like, Wait…I don’t wanna do this. I don’t have to go on dates. Now, I meet people when it feels natural, but I’m not putting pressure on myself to get out there if I don’t feel up for it.”
“After using Bumble for a little over a month, I found a guy who seemed to be ‘perfect’ for me. We talked through the app and via text message for months before we finally pulled the trigger and decided to meet IRL. Our first date was at a Mexican restaurant in the Financial District. I thought it was destined to fail because I generally hate Mexican food…and upon meeting him, I found that I wasn’t really attracted to him in person.
“On the other hand, his personality was incredible. I had so much fun talking to him. And better yet, the sex was AMAZING. So, we continued to see each other somewhat frequently. After starting to get closer, I told him that I was writing a novel and wanted to have it published. As it turned out, his best friend was an editor at a publishing company. He connected us…which resulted in my first book deal for $100,000!
“In the end, the two of us didn’t work out romantically. We just weren’t right for each other. But he and I have remained really close friends!”
“This is kind of a crazy story, but a few years ago, I met a girl for a first date in a café in downtown Austin. She had a friendly relationship with the wait staff and we chatted with them. I was looking for work at the time, and one of them mentioned they had an opening. I ended up working there for like two years, and the people became some of my closest friends in Austin. The girl who actually took me there? We’re friendly! But it didn’t work out between us.”
“I slept at a girl’s house recently and she had two cats. Apparently, I’m extremely allergic — somehow, I didn’t know. Literally thought I was going to die. I guess I’d never been around cats in such close proximity before? Obviously, it wasn’t going to work out between us…because of the cats. But that actually turned out to be incredibly important information, being that I was planning on moving in with a dude with a cat when my lease ran out.”
“After ending a relationship I’d been in for nine years (read: my entire adult life), I turned to Bumble to take on the single world. I wanted to meet people, go on dates, have one-night stands!
“The first guy I met, however, was amazing. We had an incredible first date, and our sexual chemistry was insane. I felt the connection instantly but didn’t want to get caught up in it, since I was so new to single-hood.
“I went on several more dates after that — probably a few a week. But all the while, I couldn’t get the first guy out of my head. Even after dates that seemed to be going super well, I found myself going over to his place at the end of the night rather than finishing the evening with the person I was actually out with.
“And, well, what can I say? Three weeks later, we were seeing each other pretty steadily. Now, a year later, we’re still together. And in part, I owe it to all those dates that didn’t work out. They were the ones that confirmed for me that I really did want to be with him. It wasn’t a fleeting thing. No matter how good the date, nobody else could compare.”
Like what you see? How about some more R29 goodness, right here?