c/awkward-date-stories

The time I accidentally showed up to a coffee date in my old high school uniform

This was back in 2016, right after I graduated. I had this bright idea to meet a girl at a Starbucks near my old school because I was nostalgic. I forgot I was wearing my old cheerleading jacket from sophomore year with the school logo on it. She laughed so hard when she saw me, and I just turned bright red trying to explain it was laundry day. Now I always double check my outfit before I leave, even if it's just a quick errand. Have you ever worn something super embarrassing without realizing it on a date?

The time I took a girl to a cat cafe and she turned out to be allergic

I spent like 3 weeks planning this date with this girl I met on Hinge. Found this cool cat cafe in downtown Portland that had like 20 rescue cats roaming around. Seemed perfect because she said she loved animals. We get there, order coffee, and within 5 minutes her eyes are watering and she's sneezing like crazy. Turns out she's super allergic to cats but thought she could power through it lol. We lasted maybe 20 minutes before we had to leave. She was cool about it but the whole vibe was ruined. Has anyone else had a date plan backfire because of something dumb like this?

The shift from dinner-and-a-movie to hiking dates felt weird at first...

I used to do the whole restaurant thing every time until I took someone trail walking near Lake Tahoe and realized you actually talk way more when there's no waiter hovering over your table, has anyone else switched to activity dates and noticed the same thing?

My first real date in 15 years ended with a broken shoe and a car that wouldn't start

I got back into dating after my divorce last fall, and on Tuesday night at a diner in Lansing my heel snapped off walking to the car... then the battery died. Has anyone else had a date where everything mechanical just gave up on you?

Vent: wasted $90 on a fancy restaurant that served me raw chicken

I took this woman to a trendy new Italian place downtown, and my chicken parmesan came out pink in the middle. The waiter argued with me that it was just the sauce color, but I saw the texture, I know what raw chicken looks like. I had to sit there for 20 minutes waiting for a new plate while she finished her meal, and the conversation just died. Has anyone else had a date ruined by bad food at a place that was supposed to be nice?

That awkward dinner where I tried the 'compliment sandwich' trick

I was on a third date at a little Italian place in Denver and kept stumbling over what to say, then I remembered a friend's advice to just ask about their weirdest hobby and it totally saved the night. Has anyone else found that one random question that breaks the silence?

Comparing blind dates from 2005 vs now is a total different world

Back in 2005 I went on a blind date a buddy set up and we met at a diner. No phones out, just awkward small talk about my plumbing job and her work at a dental office. We lasted maybe 45 minutes and I paid $12 for two coffees and a slice of pie. Fast forward to last year and a friend tried setting me up again, but she spent half the dinner scrolling Instagram. I ended up showing her photos of a pipe burst I fixed which was somehow less awkward. Anyone else notice how phones wrecked the flow of first dates over the past 15 years?

My date at a coffee shop last Tuesday ended with me spilling latte on her dog

I finally got the courage to ask out this girl from my gym. We met at Brew & Bean on 3rd Street. Everything was going fine until her little chihuahua jumped on my lap and I jerked back, sending my whole latte flying onto the dog. She had to leave early to wash him off at a pet groomer. Was it the dog thing or was she just not into me from the start?

Found a trick that saved my awkward dinner date last night

I was at a loud restaurant and we kept having those painful silences. So I asked her what her top 3 favorite snacks were and she talked for 10 minutes straight. Has anyone else tried a simple question like that to fix an awkward pause?

Hit my 10th date where someone brought up their ex within the first 20 minutes

I keep a running tally in my notes app. 10 dates in 2 years, every single one of them dropped an ex story before the appetizers even showed up. Last one was at a diner on 3rd street, she spent 15 minutes talking about her ex's weird sock collection. Is this just the standard now or am I attracting a certain type?

I used to think a dinner date should always end with a kiss. Now I think that expectation ruins things.

Back in my 20s, if a date didn't end with at least a peck on the cheek, I'd feel like it was a complete failure. I'd sit there replaying every thing I said, wondering what I did wrong. This one time in 2017, I went out with a guy from my yoga class. We had a great two hours talking about hiking and his dog. At the door, I leaned in and he just froze. I got in my car and practically drove home in tears. A friend told me I was probably coming on too strong. It took me a few more awkward tries like that before it clicked. Now, I just see the first date as a chance to see if we can have a decent conversation without any awkward silences. The kiss pressure just feels hollow and forced to me now. Has anyone else shifted their thinking on what makes a first date a success?

That Italian place on 6th st ruined my date last night

Took a girl to Angelina's Ristorante downtown. Thought it would be romantic. Waiter kept calling me 'buddy' and she ordered the spaghetti. She twirled it so loud the whole table looked. Then she got sauce on her white shirt and blamed the cheap napkins. Has anyone else had a restaurant totally kill the mood?

That sushi date in 2005 where I grabbed the wasabi pile like it was guacamole

I was 22 and took this girl to a pretty legit spot in Portland. She ordered for both of us and I was trying to act cool. The server set down a little green lump next to my roll and I scooped the whole thing into my soy sauce like a complete idiot. She just stared at me while I coughed for a solid minute. We lasted two more dates after that but I never lived down the wasabi thing. Anyone else have a first date food moment that killed the vibe?

Had a date ask me how many kids I wanted before the appetizer came

Met this girl on Hinge in Austin. Five minutes in she asked if I want 2 kids or 3. I said I don't even know what I want for dinner yet. She got quiet and the rest was awkward silence. Has anyone else had someone jump to serious stuff way too fast?

Spent $200 on a speed reading course and realized I just needed to stop scrolling on my phone for 10 minutes before dates

Bought this fancy online program promising I could read a whole book in an hour but after three sessions I noticed my focus was shot from checking Instagram every two seconds, and the real issue was just putting my phone in another room so has anyone else wasted cash on a fix that was basically just a habit shift?

Took a date to a fancy restaurant last week and my card got declined

I'd been saving up for weeks to take this girl to a nice Italian place downtown, and when the check came my debit card just got rejected right there at the table. Turns out I'd accidentally set a $50 daily spending limit on my banking app and forgot about it months ago. Has anyone else had a date get derailed by something dumb like a technical glitch or misclick?

Serious question, is the 'awkward silence' on a first date always a bad sign or just a normal thing?

I had a date last Friday at a pizza place downtown. We talked fine for the first 20 minutes but then we just sat there for maybe 30 seconds not saying anything. I felt super awkward and started rambling about the weather. My friend says it means there is no chemistry and you should just leave. But I also think sometimes people just need a second to think or eat their food. What do you guys think? Is a quiet moment actually a red flag or do some couples just need to get comfortable with the pauses?

Rosemary oil for hair growth felt like a scam until I tried it for 2 months in Denver

I was convinced it was just influencer hype until I measured my hairline with a tape measure and saw a 1/4 inch of new baby hairs by week 6. Has anyone else had actual results from cheap natural remedies or am I just lucky?

That girl who ordered a salad then ate half my fries

She said she wasn't hungry and then pouted when I didn't offer her more of my burger. Three months later she's still posting thirst traps on Instagram with her new gym boyfriend, guess she found her protein.

Tried the fancy steakhouse for a first date vs a dive bar and oh boy

The steakhouse guy kept talking about his watch collection and the waiter spilled red wine on my only nice top. Dive bar dude bought me a PBR, we played pool, and he actually asked me questions about my job. Has anyone else found that spending more money makes the date feel more awkward not less?

Had a date cancel on me an hour before dinner - but the REAL awkward part was I ran into her at the SAME restaurant 20 minutes later

My date took 4 hours because I ordered the wrong shoes online

So I matched with this guy on Hinge and we planned a casual coffee walk downtown. I ordered these new boots online saying they'd arrive in 2 days but they showed up the day of the date and they were 2 sizes too big. I spent 45 minutes trying to stuff insoles in them and they still flopped around. Ended up being 20 minutes late because I had to dig out my old sneakers from the back of my closet. The coffee shop was almost closing by the time I got there and we only had 15 minutes together. Has anyone else had a date ruined by bad online shopping timing?

Can we talk about the 3 date rule?

I read this stat online that 78% of people still expect sex by the third date. But my last date ghosted me after date two because I wanted to take it slow. Which side is more normal now, the old rule or just going with the flow?

Dropped $40 on a 'romantic' gondola ride in Venice and it was the most awkward hour of my life

Tbh I thought a gondola ride would be this super smooth romantic thing, but my date and I sat there in total silence while the gondolier sang loudly in Italian. We couldn't even make small talk because he was right there listening to everything. I paid $40 cash for a 45 minute loop through the canals and it felt like an eternity. My date kept checking her phone and I just stared at the water wishing I could jump out. The worst part was when we got off and she said 'well that was weird' and walked away. Has anyone else had a paid activity totally kill the vibe on a date?

Overheard a waitress say her date ordered for her without asking, made me rethink my last date

She told the host it was the biggest red flag she ever saw and I realized I did the same thing to my date last month, has anyone else had someone order for them and feel totally dismissed?