15 Most Embarrassing First Date Stories From Reddit

Here are 15 hilarious, embarrassing, and kind-of disturbing first date stories from Reddit. These will either make you feel better about your crappy dates or never want to go out in public again. There’s no in-between, and I’m not sorry.

A Not-So Blind Date

Reddit user Aregisteredusername shared his most embarrassing first date story: “When I was 21, I agreed to go on a blind date with a friend's new girlfriends friend, more or less so he could get laid or something, idk. So I arrive about twenty minutes early to the restaurant and take a seat at the bar. I didn't actually drink, still don't, but it felt right. Anyway, in sitting there waiting for a girl in a blue dress, hair up in a braided ponytail, to come in. That was every bit of information I had on her. In walks my ex, from about two years ago, in a blue dress, with her hair up in braids. I saw her, turned my back as she walked past me to the end of the bar, and I got up and bolted. I explained it to my friend and his girlfriend and they bursted out laughing, then apologized. His girlfriend said she got a call from the blind date saying she got stood up and she was sad, then it was explained to her and she was glad.”

People like to say that there are a lot of fish in the sea (which is true), but stories like this one prove how small the world really is. This is especially true if you’re dating in a small town or in a college town, where everyone knows everyone.

How To Lose a Date in 10 Minutes

IQ818 wrote about her worst Tinder experience: “A date asked me to marry him within the first hour of meeting. He said he married his first wife within 3 weeks of meeting her and his second wife within 2 weeks of meeting her. He was trying to break his own record of marrying his 3rd wife within one week of meeting her. I thought he was joking and went along with it until we got in a taxi and he told the driver to take us to city hall. I got out, said I have somewhere I have to be, and blocked his number.”

I can’t tell what’s a bigger red flag: this guy looking for a third wife or the fact that he asked a woman to marry him within an hour of meeting. Is he addicted to getting married and then getting divorced right after? How old is this guy? Where are the wives now? I have so many questions.

You Have What in Your Trunk?

Reddit user Xie8 wrote about a creepy first date she went on: “Went out on a date with a guy that asked for my number while I was at work. He was cute so I figured I'd give it a shot. Well, he took me to Waffle House and proceeded to say, ‘Why did you come out with me? For all you know I could have a dead hooker in my trunk right now.’ I nervously laughed and tried to get out of there as fast as I could. Creepy.”

I have a relatively dark sense of humor, and I only bring this up because the comments were arguing that he was just joking, but I think this guy was crossing the line. I remember reading a story of a girl getting murdered on a Tinder date while hiking, so I totally get why this girl was horrified and didn’t want to risk it.

A Not So Number One Date

Blacktara wrote about one horrible first date she went on: “Met a guy for a walk-and-talk through my favorite park. We had a nice vibe online and I had hopes we'd at least have a good time even if we weren't attracted. He was completely bizarre. Spent a lot of time trying to get me to believe that he was some sort of psychic or wizard with magic powers, asked for a ride to the bus station from the park (I had no idea he hadn't driven himself there) and suddenly had to pee during the 5-minute drive. Wet his pants just before getting out of the car.”

This is when Venmo request comes in handy. Send him that car cleaning bill, girl! Even Harry Potter can hold his pee for five minutes.

A Slippery First Impression

Therapy_works described her most embarrassing first date: “My freshman year of college, I went on a first date with a guy from my Italian class. We had pizza and after dinner, we were walking around and it started to drizzle. I was wearing ballerina flats with no treads. I took a step on the wet cobblestones and my foot shot out from under me. I landed on my ass, hard. I was mortified, of course, so I stood up quickly. My date asked if I was okay. I remember saying that I felt queasy... and the next thing I knew I was regaining consciousness in the gutter. A woman stopped to help. I eventually got up and finished my date at the student health center. It turned out I'd broken my tailbone. I had to sit on a donut cushion in class for the next two weeks. It didn't work out. It's too bad because breaking my ass on our first date would have made a great ‘how we met’ story.”

This story not only made me laugh out loud because it’s so mortifying, but it would've been even better if she ended up marrying this guy. It would have been the perfect start of a real-life romantic comedy, but at least she got a hilarious story out of it.

Plot Twist

User novags500 shared his worst first date story, but it had a surprisingly happy ending. He wrote, “The worst date I have ever been on. awkward dinner, go to a bar (I know classy right?) Get drunk (both of us) she runs into some college friends, ditches me for about 45 minutes. I hang in there getting more drunk and pissed, by the time she comes back I'm wasted. Tell her what I think about her, she apologizes. Married her a year later. Still with her. love of my life but the WORST first date I've ever had.”

I would pay to watch this couple tell this story to their children. This might be the most surprising “how we met” story I’ve ever read, and I’m here for it.

Over Before It Began

One user didn’t even make it to the first date and described how he (almost) got there: “We decided on meeting at a bar for our first date. I got there ten minutes early and soon got a text saying she would be a half hour late. In that half hour I managed to get myself kicked out of the bar. I ended up canceling the date out of embarrassment and never saw her again.”

How did this guy get drunk enough to get kicked out of a bar in less than 40 minutes? Forget about the date, this is the question I want answered. Did he chug five shots in under a minute and hit on the bartender or something? If so, it looks like this girl seriously dodged a bullet.

Middle School Heartbreak

Middle school is already tough, but dating in middle school can be brutal, as a user named LilSousa said, “Girl and I made plans to meet at an outdoor mall and see a movie, this was back in middle school so my mom had to drive me in about an hour’s worth of traffic, and she cancels 15 minutes out. I felt so bad for my mom driving me all the way there already so I simply pretended like she hadn’t canceled, my mom dropped me off, and I watched a movie by myself. Almost cried but I kept it together. But I mean the movie was good at least.”

I can’t get over this story because it perfectly describes the awkwardness of middle school. It makes me so sad to picture this kid sitting at the movies by himself, but I can’t help but imagine him looking out of the window while his mom drove him home like he was in a depressing and dramatic music video.

Church Boy Gone Wild

Dating a guy you meet at church sounds like a good idea because it means you share religious values…but that doesn’t mean the date will go well. A user named CaffeinateMeCaptain writes, “I was around 17 or 18. There was this guy at my church that I wasn't super interested in, but my parents really wanted us to at least give it a go because they thought he was a good guy. He was funny and traditionally attractive, I just wasn't personally attracted to him. So when he asked me out on a date one day, I'm like eh sure, what's the worst that could happen?” 

She continues, “Well, he took me to Penn Station. A casual sub chain, for those that don't know. I'm not a stickler about going to expensive restaurants or doing anything fancy for dates, but a sandwich chain with a drive through? Eh. My food was horrible. I couldn't finish it and was nauseous the rest of the night (I still can't bring myself to eat there.) So after that he's like ‘I have a friend throwing a party, want to go?’ And I'm like ‘Hell yeah, that's more my speed. Church boy is getting crazy.’ We walk into this tiny, dirty trailer packed with people I didn't know. The only seating was a single couch, and there was a random-ass strobe light in one room. Everyone was just sitting on the floor. He immediately left and got a drink so I'm like ‘ight, guess I'll be the DD.’ He didn't introduce me to anyone. Everyone kept asking why I was drinking water and if I wanted a drink, which I desperately needed at this point but turned down. He was nearly impossible to find for most of the party except for the last 10 minutes where I sat on his lap and we made out. He was an awful kisser. By then, it was late, I was uncomfortable, still nauseous, and a good 45 minute drive from home. I asked to leave several times before I finally dragged him out and drove his drunk ass home. There wasn’t a second date.”

Not only is this hilarious, but I’d love to know what it was like seeing him at church the following Sunday. Let the eternal awkwardness commence!

Commando Oh-No!

One user hilariously told the story of why you should always wear underwear on a first date. She wrote, “I didn't have time to finish laundry before my date, as a result, had no dry underwear to wear. I had to make the decision: 1) wear wettish underwear and be uncomfortable and risk displaying unsightly crotch wetness through my pants, 2) wear no underwear and fly free (didn't see any negatives at the time). I went with option 2. We get to the restaurant, they seat us in a booth with those hot vinyl seats. The dinner goes well, great conversation, good laughs. The place was really hot, and I had been drinking water all night, so I had to use the restroom. I go to the bathroom, and notice that there is a line of sweat right along my ass crack, clearly visible from the back. F***. Given the direction of the walk to the restroom, my date definitely saw it. Oh well, shrug it off, what's done is done. Walk back to the table, finish the date. No second date.”

Lessons learned: always plan laundry ahead and wear underwear on a first date. Better safe than sorry.

Narcissist Much?

Some bad dates make hilarious stories, some are near-death experiences, and some are both – and user thirdwavefresh can attest to that: “Went on a date with a Navy boy, he seemed smart and sweet online. He picks me up in this incredibly ostentatious yellow Camaro, which I have the sneaking suspicion he borrowed as it was a stick, and the dude was having a helluva time driving it. We decide to go walk on the boardwalk for a while, so he pulls into a parking garage. In his attempt to park the car, he completely sideswipes the car next to us - leaving yellow paint all across their car. He didn't even act like anything happened, so I say, 'Umm, I think you may have hit the car next to us.' He gets out looks at it, then climbs back in and goes, 'I guess we should park somewhere else' and peels out before I could even say anything.”

She continues, “Fast forward, the date is going poorly (as a hit and run is never a good start), and it's miserably hot out so we decide to see a movie. It happened to be Shrek The Final Chapter – a kid's movie. He has his feet on the seats in front of us, which is no big deal, until a dad holding his toddler daughter comes in and the only seats still open are the ones in front of us. The dad goes to sit down – Navy boy doesn't move his feet, in fact he even moves his feet forward a bit so that he hits the dad in the head. The dad looks back at us, and then Navy boy sighs heavily, takes his feet down, looks at me and goes, 'My feet were there first.' After the movie he asked if I wanted to go to dinner, I said no, he drops me off (I'm surprised he didn't drop the transmission as well...) and asks when he can see me again, he had a great time.”

I can’t tell if this is hilarious, horrifying, or both. Ok, it’s definitely a bit of both, but it goes to show that when someone shows you who they are (like this loser on the first date), believe them.

Poor Table Manners

Poor table manners on a date are a big turn-off, as user bablueyed5 writes, “I've told this story on reddit before, but it's always a good one. I went on a first date and the guy was a bit odd, but okay that's cool. I can do odd. He had a bachelor's degree in IT, but was unemployed and living in his grandma's house. Not my idea of a turn on, but I can deal. We went to Indian food, which I love. We enjoy the food and talk a bit more. He had never had a long term relationship and had only slept with one girl... So yeah, lots of fun red flags at this point, but I like conversations and the guy seemed a bit lonely.”

She continues, “So dinner is winding down, and I'm contemplating my exit strategy for afterward. Then... it happened. Dinner was over. We were about to head on our way. Before we could though, he picked up the plate and licked it. Licked it clean at that. Not just a single lick, but the whole god dammed plate. After my amazement subsided, he invited me back to his, well his grandma's place. I politely declined of course, and did what I think is a favor. I sat him down and explained some of the things he did wrong over the date. I hope he used the information I gave him for his next date.”

I’m sorry, I can’t get over the fact that this guy thought it was socially acceptable to lick his plate in public? I knew that was inappropriate when I was a little kid, but this grown-ass man is doing it on the first date. Good on this girl for being kind about it, but I would have so many questions for his grandmother.

Extreme Catfish

If you’ve ever seen Catfish, you know that some people have weird reasons for lying about who they are on dating apps. This story by a user named hp94 takes it to another level: “A friend of mine set up an account for a presentation on the 'successes of modern technology on the dating scene'. His final report included a great story - He met up with a girl who was using her daughters photos for herself, saying she was 25 online but was really 55, and said she had no ethical problems lying online as long as she told the truth while in person. To top it off, she was on her third marriage and had multiple facebook accounts.”

I don’t know where to start with this one. This woman is literally on her third marriage and was using her 25-year-old daughter’s photos to catfish guys on dating apps, all while she appears to still be married to her third husband. And she saw nothing wrong with this? And what’s with the multiple Facebook accounts? Is she pretending to be her daughter on Facebook too? Does her daughter know? I need a Netflix documentary on this ASAP!

Worst Night Ever

Sometimes nerves get the best of us and can ruin a great date, as KGypsyB writes, “I went on a date with this guy and everything was great. we went to dinner then back to his place and watched a movie. however, when it was time to go, i suddenly became SUPER nervous (didn't know whether to kiss him or not). i ended up backing into a curtain then backing into him then tripping over my shoes then backing into a chair after getting my leftovers causing me to almost spill everywhere. He just kept asking if i was ok.......when i got into my car, i turned a corner and my leaky roof dumped about a cup of water into my lap. great night.”

Who else can relate? First date (and even more, the first kiss) nerves are very real. I hope she reached out to this guy and went out with him again because he probably felt just as embarrassed. We've all had awkward first dates that deserve a second chance.

So Many Red Flags

Sometimes a first impression is all you need to know a person isn’t right for you, as a user named blurp_taco writes, “Went on one date. He would not stop talking about his ‘gorgeous’ ex-wife. Also mentioned being a lawyer, his huge house, and what a manwhore he'd been since his divorce about a million times. Was very self-absorbed and clearly just looking for hook-ups. Texted me the next day: Him: The fun committee is meeting at my house tonight. Me: The fun committee? Him: Yeah you and me are the only members. Me: …”

I’m convinced this guy is a serial killer. Who says “fun committee” unironically? It gives off similar vibes to Armie Hammer's texts about cannibalism, and if that isn’t a giant red flag, I don’t know what is.

Closing Thoughts

Some first dates are great and some first dates are terrible, but let’s be honest, terrible first dates are a lot funnier…at least in retrospect or when they happen to someone else!

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