c/awkward-date-stories

Spent 80 bucks on a fancy dinner and she ordered a side of fries because nothing else looked good

We sat there for 45 minutes while she picked at those fries and I ate my steak in silence, so was the money wasted or did I just dodge a bullet early on?

I spent the whole dinner talking about my ex without realizing it

It wasn't until she asked if I was over my last relationship that I stopped mid-bite of my burrito and went oh no. Third date and I just kept circling back to stories from 2 years ago without noticing. Has anyone else had that moment where a date calls you out on your own garbage behavior?

That time I compared two date spots and one was clearly the wrong call

Took a girl to this trendy taco place downtown called El Fuego. Loud music, $14 margaritas, and we had to shout at each other for an hour. Next week I suggested a quiet dive bar on Elm Street. Much cheaper, could actually talk, and she laughed more in 20 minutes. Which date setup actually works for real conversation?

Rant: Why does every first date turn into an interview? I finally cracked

Went on a date last weekend with a girl from Hinge. Within 5 minutes she was asking me about my 5 year plan, what my love language is, and if I want kids. Felt like she was reading off a checklist she found on TikTok. I get wanting to know someone, but it's like people forget dates are supposed to be fun. What happened to just letting a conversation flow naturally? Has anyone else stopped caring about "vetting" and just started enjoying the awkward mess of getting to know someone?

Remember when coffee dates meant a quick meetup not a whole production?

Met this girl at a diner in Portland back in 2012 and she spent the first 15 minutes taking photos of her latte for Instagram before even saying hi. Has anyone else noticed dates turning into photo shoots instead of actual conversations?

Hit date number 50 this month and I'm starting to think I'm the problem

Met someone new on Tuesday and realized it was the 50th first date I've been on since I started keeping track in 2022. Fifty. That's almost one a week for a year. I keep a little note in my phone of where we went and what went wrong. Most of them are fine people, just no spark or they ghost after. But 50 feels like a weird milestone. Like at what point do I stop and think maybe I'm doing something wrong that I can't see? Or is this just normal for dating apps now? Anyone else hit a number that made them stop and question everything?

Hit my first good date after 8 awful ones in a row

I finally had a date last Friday that didn't end in awkward silence or me tripping over a curb. She laughed at my dumb joke about my dog stealing my sock, and we talked for two hours at a coffee shop in Austin. The last 8 dates were disasters, like one guy who spent the whole time complaining about his ex. I honestly thought I was cursed or something. Has anyone else had a streak of bad dates turn around out of nowhere?

Overheard a waitress say 'he ordered filet mignon on the first date' and realized I was that guy

Took my date to a steakhouse last Friday and ordered the most expensive thing on the menu trying to impress her, but she later told my buddy's girlfriend I came off as trying too hard.

Got told I talked about my ex too much on a date, so now I keep a mental timer for how long I let myself vent about past stuff.

She straight up said 'you sound like you're still processing that breakup' after I mentioned my ex's cat for the third time in an hour, so has anyone else gotten a brutal mirror held up to them mid-date and actually changed how they act?

Took my date to a drive-in movie theater last summer and forgot how awkward the pause between movies is

Back in the 90s, my high school girlfriend and I went to the local drive-in near Columbus, Ohio, and we had 15 minutes of dead silence between flicks because I panicked and couldn't think of anything to say. I tried making a joke about the bugs on the windshield and she just stared at me. Anyone else have that weird gap where you realize you have zero chemistry?

The car door that refused to close on my date's side

I picked her up in my old 97 Civic, which I normally drive 6 days a week with no issues. We head to this diner downtown and she gets out first, but the passenger door won't latch shut no matter how hard she slams it. I had to hold it closed with a bungee cord from my trunk for the whole 15 minute drive back. How do you recover from having to tie your date's door shut with a rope?

That time I asked my date if she wanted to split the bill and she walked out

I was at this Italian place in downtown Portland. Things were going fine, talking about work and whatever. Then the check came and I just asked if she wanted to split it 50/50. She stared at me for a second, said "you're kidding right" and then literally got up and left. I sat there for 5 minutes before the waiter came back. Has anyone else had a date end over money talk that quick?

My Tinder date called me out for over-explaining and it stung

I went for coffee with a girl named Jess at a spot in Portland last Friday. She asked why I like hiking and I gave her a 5 minute ramble about elevation gain and trail maintenance. She just said 'you do that a lot, don't you?' and she was totally right. Has anyone else had a date point out a habit you didn't even notice about yourself?

Took a date to a fancy restaurant and my credit card got declined for a $85 bill

I had this whole thing planned at a place in Portland, nice dress and everything. The waiter came back with the terminal and my card just kept saying denied. I had to call my bank right there while she stared at her napkin, turns out they flagged it as fraud. Anyone else have a payment fail at the worst possible moment?

The night I tried to impress a date with my cooking and set the smoke alarm off

Back in my early 20s, I used to think the best way to wow a date was to cook something fancy from scratch. I remember one time I invited a girl over and tried to make a lemon butter sauce for some fish. Within 5 minutes I had the pan too hot, butter burning everywhere, and the smoke alarm went off so loud we couldn't hear each other talk. The whole apartment filled with smoke and I had to open all the windows in January. She just sat there on the couch looking at me like I was a total disaster. Now I just order pizza or pick a decent takeout place before the date even shows up. Why do we think we have to be these perfect chefs just to impress someone? Has anyone else totally fumbled a home cooked date meal?

Six months ago I was the funny one on dates. Now I'm just the guy who talks about work.

I went from cracking jokes that got laughs to rambling about customers and inventory within like 5 dates after I started managing the hardware store. Has anyone else had their conversation skills totally die after a job change?

Hit 12 awkward date milestone in one month that surprised me

I went on 12 dates last month and every single one had at least one super awkward moment. The one that stood out was when a girl asked if I still lived with my parents and I accidentally said 'yes' while chewing a big bite of burger. She got quiet for like 10 seconds and then asked the waiter for a to-go box. I thought I was doing fine but that one answer tanked it. Has anyone else hit a weird number of bad dates in a row like that?

I finally gave the ramen place on Elm Street a second chance after a bad first date there

So I had this really awkward date at Ramen House on Elm about 6 months ago. My date spent the whole time on her phone and the service was super slow, so I swore I'd never go back. Then last week my buddy dragged me there for lunch and I noticed the owner had completely retrained the waitstaff. They brought out fresh noodles in 5 minutes and the broth was way better than I remembered. Has anyone else had a bad first impression of a place turn around like that?

That time my date spent 20 minutes explaining his bike chain to me

So I went on a coffee date with this guy from Hinge about 3 months ago at a Starbucks downtown. He seemed cool in messages but as soon as we sat down he whipped out his phone and started showing me photos of his bike chain from different angles. Not his actual bike, just close ups of the chain links and sprockets. He went into this whole thing about grease grades and how he had to replace a link after a ride in the rain. I sat there nodding and sipping my latte for like 20 straight minutes without getting a word in. Eventually I just said "hey, I gotta run" and he looked genuinely confused. Has anyone else dealt with a date who just wouldn't drop one weird topic?

Went on a date last week where he brought his mom to the restaurant

It was at a place called The Rusty Anchor in Seattle. He said she was just 'in the neighborhood' and wanted to say hi, but then she sat down and ordered a full meal. Has anyone else had a parent show up uninvited?

The time I realized my 'funny' stories were just me being a jerk

I was on a third date at a pizza place in Cincinnati, telling my usual bit about a nightmare client from last fall. I said, 'So I told the guy his roof looked like a toddler's art project,' and she just stared at her plate. She finally said, 'You seem to enjoy making people feel small.' It hit me that for years, I'd framed every date story as a sarcastic win, but I was just the bully in them. I spent the whole drive home replaying a dozen old jokes that weren't funny. Has anyone else had a moment where they saw their own stories in a totally different light?

I read a study that said 34% of first dates end because someone brings up an ex, found it in a psychology journal at my old college library.

TIL my attempt at a 'no phones' date at a quiet Italian spot in Providence backfired when the waiter dropped a tray of drinks right behind my date, making her jump and spill her wine all over my shirt.

We spent the next 20 minutes in the bathroom with paper towels trying to get the stain out while a line formed, and I learned that trying to force a perfect, distraction-free vibe can make a small accident feel like a huge deal, so has anyone else had a plan for a smooth night go completely sideways from one random thing?

Okay so I used to always pick the restaurant for a first date...

I'd spend hours looking up a cool spot, trying to impress. Then, a guy I met last year in Austin just sat there silently for 20 minutes because he hated sushi and I'd picked a sushi bar. Now I always ask, 'Any food you absolutely won't eat?' before making plans. It's a simple text that saves a whole evening of awkward silence. Anyone else have a go-to question they ask before meeting up?

Heard a guy at the coffee shop say 'I just go on dates for the free food'

I was grabbing a coffee yesterday and overheard the guy at the next table bragging to his friend about how he schedules dates around mealtimes just to get a free dinner. He said, 'My budget is tight, so it's a solid strategy.' I mean, idk, that just feels so messed up and made me think about my own past dates. Has anyone else encountered someone who was clearly just there for a free meal?