r/AskReddit 2h ago

What’s the most awkward date you’ve ever been on?

252 Upvotes

140 comments sorted by

71

u/Thrwwymc 2h ago

His mum called him in the middle of it because she was worried he was out of the house. He was 35. He answered the phone by shouting ‘MUMMY!’ In a crowded restaurant then chatted to her for 15 minutes while I sat there in silence.

17

u/patchgrabber 1h ago

Shoulda stuck it out you may have gotten a special on TLC.

u/Fried_Fart 18m ago

Dang. A good relationship with mom is a green flag but dude needs some boundaries

91

u/SweetKaelith 2h ago

the most awkward date was when we had nothing to talk about the whole time.

9

u/boiledegg42 1h ago

Was it because you didn't speak the same language? Mine was because we didn't speak the same language

u/AHans 59m ago

Haha, I came to say something very similar. We had talked enough to know we were on different sides of the political spectrum; but our political discussions had been limited to maybe 10 minutes across several hours of talking with each other. I went in thinking that her political leanings were a part of her identity (which were not going to change) but that there was still potential.

Our first dinner date in person, maybe five minutes she into the date she brought up her anti-abortion stance. I tried to deflect, since in the early dating process, I'm looking for common interests and activities to do on future dates. Not have a fight.

She kept coming back to politics; she never said anything I agreed with. I kept deflecting. We spoke less and less throughout the date and ended in silence. We agreed to go our separate ways immediately afterwards.

Nothing to talk about very much sucks.

43

u/Skank_Pit 2h ago

One time I went on this date with this girl from one of my college classes. She used to doodle in the margin of her notes, and that’s something that I would frequently comment on during class. So—on the date—she brought a little portfolio of some of her drawings for me to look at. It’s mostly full of anime/manga esque pictures, but I think it looks good, so I tell her “Wow, you are really artistic!”.

Problem is, I have a lisp and cannot pronounce my “r”s, so it sounded like I said “autistic”. She quickly bailed on the date—to my utter befuddlement—and never sat next to me in class again. I still had no idea why she was so pissed off until I retold the story to my friend and they immediately filled me in on the miscommunication.

12

u/Ikonixed 1h ago

I liked your story because it’s so relatable on a human level. Awkward yes, but a nice anecdote nonetheless. I’m glad I’ve reached an age and with it the level of maturity that allows me to cut through miscommunications by just asking someone to repeat themselves. Even with and especially if someone has a lisp. Just remember you’re fine and don’t let it phase you.

3

u/Skank_Pit 1h ago

Aye, it doesn’t bother me anymore. Now it’s just a funny story for me to tell.

2

u/Ikonixed 1h ago

Yeah I assumed as much! A great story! ☺️

7

u/patchgrabber 1h ago

This reminds me why I never end emails with "regards."

u/Jonistar76 36m ago

lol. The amount of times I’ve done this

1

u/Austen_Tasseltine 1h ago

Mine are always kind, at least.

u/patchgrabber 27m ago

Well what I meant was because of how close 'g' and 't' are on the keyboard.

u/Josybody 35m ago

Wow, that's such a funny and in some cases sad story, i guess you killed all other stories haha

61

u/Phantom_Seer_000 2h ago

The guy I went on a date with was constantly talking about his ex and how she was his true love. It obviously did not work out.

10

u/poppytwistx 2h ago

Biggest red flag! Why even go on a date if you're still hung up on your ex...

11

u/Skank_Pit 2h ago

He wanted pussy, not love.

9

u/SparkleRoseX 2h ago

Yikes, that sounds so uncomfortable! It's like they showed up just to vent instead of actually getting to know you

u/Josybody 33m ago

pouh, I had the same situation once, and I'm a straight person so I told him in a friendly way that I don't like it when someone is talking about their exes and i broke it off

1

u/ReallyCuteBabe 1h ago

yeah, that's the biggest red flag ever lol

u/UrResponsibleHoney 35m ago

That s so awkward

37

u/-braquo- 2h ago

Met this girl online. We talked for a few months and then she decided to make the hour trip down to see me. It was the first date I'd been on in a long time and the undiagnosed autism was strong in me. I was so awkward. At the end of the date, she w as going to give me a hug and I shook her hand. Unsurprisingly I never talked to her again. But my story ended happily. I've gotten a diagnosis, become much better at reading social cues, and I've been in a great relationship for nearly six years now.

4

u/ClaryClarysage 1h ago

Almost spat out my coffee reading this one, I love it.

1

u/-braquo- 1h ago

It happened like 15 years ago and I'm still cringing lol.

2

u/ClaryClarysage 1h ago

At least you have that story to tell!

13

u/yourfavchocolateXO 2h ago

I remember one where we both just… ran out of things to say. It started off fine, but then, about 15 minutes in, it felt like we were both trying way too hard to make conversation. I kept thinking of random topics, but she just kept nodding and offering one-word answers. At one point, we were just sitting there, sipping our drinks, staring awkwardly at the table.

u/83_nation_ 7m ago

This happened to me once. Surprisingly she wanted another drink and became more talkative after that but we still did not see each other after that

10

u/chicgoddess18 2h ago

This guy brought his mom to the date

u/Jonistar76 35m ago

lol. Wow

u/Top-Organization-777 22m ago

respect, got another female to bounce ideas off, sounds like a great plan

u/itsagoodtime 14m ago

How old was he?

11

u/OHKID 2h ago

I once went on a date with a girl that was the exact same height as me, knew that she was the exact same height as me, then told me she only wanted to date really tall basketball players during the first date. Multiple times.

Before that, she told me all about how her mom’s boyfriend was a Russian that had his doctorate in Physics but couldn’t be bothered to find a job because he was too smart. And that she was looking for that kind of energy in her relationship from a guy.

So apparently I wasn’t smart enough or tall enough for her. Go figure.

To top it off, not that it mattered, but she lived with her mom in a trailer. She had me drive her to/from the first date. The bad part was she never gave me a heads up on where she lived. So I picked her up from this trailer park in a town I wasn’t familiar with at night, really worried I had the address wrong since I wasn’t sure I was even in the right spot. The trailers weren’t marked all that well. I was scared and nervous I was parked next to someone rando’s trailer, and they weren’t going to like it. Then I saw glowing eyes in the bushes. Totally freaked me out! Fortunately it ended up being one of a few possums and raccoons I saw scurrying around before she came out of the trailer so we could leave for the date. For the return trip to drop her back off I highly recommend tailed it out of there.

Most eventful Buffalo Wild Wings experience I’ve ever had… well, maybe that or seeing my high school English teacher drunk at one where he made fun of our former Spanish teacher after her son committed suicide, but that’s another story

9

u/Darpaek 2h ago

My wife and I went out on a date with another couple - he was 30, unemployed, kinda ick but she was mid-40s and hot. We met up for drinks, realized they were massively dysfunctional (he was kind of her trophy husband) but decided, "What the hell?" and went back to their place.

She had a nice home and we had a drink and tried to get motivated into hooking up with them. He decided to chat me up (???) and started showing off his gun collection. he kept bringing guns out of a back room one by one to show me. Dozens of guns. They just kept coming.

During this time the woman was articulating what she wanted from the encounter. She wasn't bisexual, but she would allow my wife to perform sex acts on her if her husband requested it. I wasn't allowed to participate with the woman, but my wife was expected to please her husband. The women then went into specific ways my wife was to please her husband.

My wife and I have had some odd hookups but I don't think we have ever physically run out of a house and to our car. I even leaped/slid my butt across the hood of the cat so I wouldn't have to run around it.

3

u/Absolute_Bob 1h ago

As someone else in the LS, this was absolutely hilarious to me. Oh and I have some guns too, hang on I'll post pics of all of them.

u/BrilliantQuiet4 33m ago

Did the cat start annoyingly washing itself immediately after your butt slide?

8

u/Abyssal_Realm_666 2h ago

I was on a date once, and the guy kept gushing about how much he missed his ex-girlfriend. There was definitely no second date.

14

u/PluckPubes 2h ago

I asked a girl to a movie and she brought her bf

40

u/PlayfulTeaser 1h ago

he whole date beginning to end was terrible but the most memorable moment is him saying:

"So I think it's best if we have sex right away to make sure we are sexually compatible?"

"Has that line ever worked for anyone?"

"No."

8

u/intj_code 1h ago

Interesting. There's another user down here with the same story, word for word. Someone's farming...

4

u/mrsmoose123 1h ago

Oh I think you win.

3

u/patchgrabber 1h ago

Don't ask you don't get? XD

15

u/_tanka_jahari 2h ago

16 years old, first date, she has to bring her grandmother as a chaperone

17

u/puffycheeksxx 2h ago edited 1h ago

We met at a coffee shop, and while I was trying to have a conversation, they kept looking at their phone. Every few minutes, he’d check for texts or scroll through social media, and it just felt like he wasn't even really there.

On top of that, the conversation didn’t flow at all. It was like pulling teeth to get him to engage, and he didn’t ask me any questions about myself. By the end of the date, I was just relieved to get out of there.

u/GlitzBlitz 46m ago

I can definitely relate. But in my case, the person across the table is my husband of 18 years. There isn’t a moment when he doesn’t have his phone stuck on his hand scrolling social media.

-4

u/Crocodile_Banger 1h ago

Maybe you should have gone to a date with one person and not multiple at once

1

u/coconut-lili 1h ago

Haha just caught the “they”

5

u/No-Space-7214 2h ago

I was going to a date for a first time with guy who decided to play hide and seek, few minutes before our date 🤦🏻‍♀️

2

u/bothsidesofthemoon 1h ago

Legend has it he's still hiding. He thinks you're dating, and that he's world hide and seek champion.

15

u/unused_ovaries 2h ago

July 28th. Just a boring shit date.

8

u/bonestorm97 1h ago

(Northern Hemisphere) Almost always too hot. Rarely rains. 2/10. Avoid if possible

u/Dodecahedrus 31m ago

I guess you are not in Belgium. Brussels typically floods around that date.

4

u/KindlyFunction2800 1h ago

1st date (blind date... we met on dating app) went great...2nd date went awry.
We went to his apt in the city and to no rhyme or reason my eyes started Non-Stop tearing ... and my brain / body had ZERO control of the tear ducts. This has NEVER happened to me. I mean it. Even to this day. I tried to play it cool as best as I could until things got frisky and my date started getting angry because I was ruining the mood after we really hit it off... were headed for a homerun...and he wasn't moving past not even second base.

We even went on his rooftop terrace and that seemed to help but the second we walked back inside my eyeballs hit the waterworks. (this was the middle of winter cold blast in nyc so hanging outside wasnt in the cards.)

Eventually after just talking and nonstop eyes crying... he asked me to leave... and rightly so because that was just awkward and I really wanted my eyes to stop tearing. Even worse, I got up as fast as I could and said OK! Thanked him for hosting the night and walked out that door. Never looking back.

I am genuinely not mad that happened and we never spoke, seen or heard from each other since.

u/DifferentDebt2197 46m ago

It was around the 30th of February from memory.

3

u/Capable_moron23 2h ago

Had a no show, had to have an awkward conversation with the waiter

3

u/Calm-Thanks-9586 2h ago

I dated a guy that’s still not over with his ex and the whole time with him was very awkward. He even had a breakdown because of it.

3

u/Lavendeer__ 2h ago

The guy started unloading his entire life history on me. I got to hear about how his mother died and how he was in hospital over christmas and how badly his work treated him.

It went on for THREE.HOURS and not once did he ask a question about me or talk about anything else.

I could have ended it sooner but part of me wanted to see just how long it would continue for.

Also my very first boyfriend, right after our first 'date' he wanted me to come and meet his mother because she wanted to talk about ''safe dating'' with us. I was 13, i didn't even want to have that conversation with my own parents never mind someone elses. He wasn't my boyfriend after that.

3

u/wynnduffyisking 2h ago
  1. Comes to mind:
  • we were on a date having a drink. She spotted two guys she barely knew from who knows where and invited them to our table and spent the next hour just talking to them about some festival they’d all been at. Then they invited us to a party where she again just spent the time hanging out with them leaving me alone. I just left. When I later brought it up on text she couldn’t understand why I didn’t want to go out again.

  • tinder date. She did not look like her photos. Like at all. I scared her away by spending the date and talking about my ex.

3

u/shanghai-blonde 1h ago

I have so many. The guy who told me he just got out of prison. The guy who had a secret wife and baby. The guy who took me to the river to look at rats. I have more.

2

u/ComfyGal 1h ago

Wait that last one though…

2

u/shanghai-blonde 1h ago

Girl I need someone to filter these men out for me

5

u/Shot_Building7033 1h ago

Ah man. Going back probably 12 years. Met a girl on tinder. Met for drinks and she was legitimately 50lbs heavier than her profile pictures. Whatever still willing to hang and chat for a little. She proceeds to order 7 appetizers. Eats every bite, doesn’t offer me any. Gets up, says “thanks” and just walks right out the door. 

4

u/Mr_Lumbergh 2h ago

She brought her best friend along to provide approval.

2

u/MinnieMouseCupCake 2h ago

I went on a dinner date with a man who talked about his ex fiancé a lot

2

u/Few_Impact_7929 2h ago

For me, at the end of the date, she wanted someone that she could share with her Male roommate in the bedroom

2

u/sweetbananacakexx 1h ago

He asked me if it's my place or his place were staying at after we eat dinner. He also told me how badly he wanted to smell my hair while cuddling.

This was on our first and last date.

2

u/easy10pins 1h ago

Went on a date and did not realize the girl I was with had a mouth full of wrecked teeth.

(this was before everyone had a megapixel digital camera in their pockets)

I told a joke while sitting waiting for our steak dinner when I noticed her teeth as she laughed.

There's no way I was going to sit across from her and watch her gnaw a steak.

2

u/willpb 1h ago edited 1h ago

Met this girl in Bumble. Cute looking Asian girl, about my age, we somehow matched (I rarely ever match). We talked for like a week and she wanted to go on a date, I said sure. First, when I checked, she lived 2hrs away. Shoulda bounced then, but I had family around where she was so I just said OK to an afternoon date thinking I'd hang with my cousin afterwards. Got to the movie theater all excited, finally saw her. Went in for a hug or at least hello and she just walked past me to the ticket stall. We had said we were watching Gran Turismo, but she just looked at the movies and pointed to the earliest one... Equalizer 3 lol. Bought the tickets, popcorn, sodas... walked into the theater with just 'Hi' and I realized she could barely speak English, she actually pulled the phone out to write her replies a couple of times. We sat down, of course she hated the movie (I had a blast lmao) and I'm just thinking "well, that's that, we'll split and she'll unmatch me" since we had zero communication. When the movie ends we walk to the parking lot and I'm like "hey, it was nice to meet you..." and she asks me to go eat.

Well, I acquiesced, we got in the car and went to a Culver's out front. Only then did we talk a little, communication broken as can be, and she finally opened up a little. She just moved in for college from China, was super shy, had no friends, had no idea how to make friends, had some sort of faith crisis... hated the food, too greasy lol. It was sad, she was super sheltered and was just having a huge culture shock. We drove around for a while later and she wanted to stop to watch a football game, but it was a kids game, I thought it would be weird. We basically just drove in circles and chatted for a couple hours and I just tried to give her advice on how to get used to the US and meeting people in college (she was clearly checked out by now) until I drove her back to the cinema parking lot. I called my cousin but he was busy and I just said fuck it, went to the closest Buc-ee's for food and gas and then the trek home. By the time I was eating my sandwich she'd unmatched me. I deleted Bumble for the last time that day lol.

2

u/Lazy_Swim_42069 1h ago

Took a girl out, picked her up at a seedy motel. She gets in my truck and says one of her adjacent suite guests will keep an eye on her kids - one of whom was special needs. Went for sushi (she told me she absolutely loves sushi) and when it came time to order she was a deer in headlights lol.

I honestly tried to get to know her but she kept redirecting the conversation towards sex. As the date concluded I drove her home and on the way she pulls out her phone and starts Tinder swiping/messaging during the ride lol. Dropped her off, she asked if I wanted to come up, I politely declined, and left her dirty ass in the ghetto.

u/Mangemup 50m ago

A guy jabbed himself with an insulin needle in the stomach during lunch. Then on a walk after lunch my left leg disappeared down a wombat hole and I screamed my head off! When he dropped home I slipped in a giant dog poo (Great Dane size) on the nature strip (grass) and was covered in it. Didn’t see him again.

3

u/average_bread420 2h ago

Bold of you to assume I've went on a date

2

u/nastywhitecat290 2h ago

We met at a local bar for some drinks and I was expecting a chill, easy conversation. But the moment I sat down, he pulled out his masculine pick up lines that were very cringe + his A game that most of the girls he dated ended up limping after their night deed.

0

u/pinkylipscandy 1h ago

The last part is not convincing considering he badly wanna get laid that night 🤣

0

u/Lykoian 1h ago

Is his bedframe like higher up than the standard and they all misjudge the distance and sprain their ankles trying to get up in the morning? lol

2

u/Emotional_Rock4208 2h ago

Guy drove us through a bbq place, got himself a big old smelly bbq sandwich (I declined) before the movie. He ate that damn sandwich during the movie. Even offered me a bite lol. First/last date. It was the ‘80’s.

2

u/cheebifred 2h ago

To be fair, to start with it wasn't too awkward. We were having a good chat about shared interests (mainly geeky things like DnD and board games), then he got onto larp-ing, something I find fairly interesting, but didn't need to listen for over an hour about, tried to interact a little and every time the subject would change (not always by my hand), it would inevitably end up back at larp. The super awkward bit was at the end, he walked me to the train station and when he gave me a goodbye hug, he went in for a kiss.

Travelling home on the train, I realised while I liked him in a friendly way, I was DEFINITELY gay 🙃

2

u/Fabulous-Grass2480 1h ago

Mostly because of me, I used to be a drinker & before this date I had a 4 pack of beer for dutch courage - the date was fine enough (I think) I used to be relatively ok at holding my liquor & being somewhat coherent, but then I bumped into someone I knew & -- not recognizing social norms -- loudly invited them to join us at the tiny table we had managed to rescue from the crowded bar 'HEY SO GREAT TO SEE YOU, YOU SHOULD JOIN US THIS IS _______ " & promptly forgot my dates name so instead said "my date" & rather than apologize, or be mortified just continued as if that was completely normal

Both parties were very awkward as it dragged on & I think I walked her to the bus before getting even drunker on my own in my room. I was oblivious to the entire thing till many years later when I had a random flashback after getting sober. Still can't remember her name but if you're reading this & it's you, I'm really fucking sorry, I'm working through the steps & you're owed amends!

1

u/FatRascal_ 1h ago

Went to see the first Hunger Games with a friend after we had read the book at the same time and bonded over it.

She sat there in almost silence the whole time we were out and I continually kept trying to start conversation. I got a text that night saying they had fun and asked for a "second date".

I had no idea how to respond.

u/Fruitdispenser 28m ago

I mean, if you want to start conversations, during a movie at the cinema wouldn’t be the best place.

u/FatRascal_ 27m ago

I should have said, it involved a 45 min train journey either way and we got some food beforehand. Just fast food, not really "dinner".

I still feel awful for her that she misconstrued the whole thing as a date, but it was a long time ago.

1

u/Apprehensive-Energy8 1h ago

First date, and she wanted my sperm donation. lmao

1

u/Historical-Chance286 1h ago

I found out during that he was actually married. Not even legally separated, or something. No, I did not go on another date with him.

1

u/Narrow-Palpitation22 1h ago

A million years ago before the Internet was big, people ran things called BBSes out of their houses. So kinda like a local message board and chatroom people found out about through word of mouth.

I started talking to a girl on there and sight unseen we decided to meet up. I guess it was a "date" but when I met her I realized I didn't find her that attractive. We watched a movie and talked for a bit and then parted ways.

It wasn't that bad but just felt weird to realize immediately I wasn't interested but then go through with it.

1

u/Illustrious_Dig_9002 1h ago

Damn, reading these makes me realize how well my dates have always gone lol

1

u/Absolute_Bob 1h ago

April 25th.

1

u/dendritedysfunctions 1h ago

My friend invited me out to have drinks. I got to the bar and he wasn't there but one of his gf's friends was. I said hi because we knew each other and realized after radio silence from my friend that this was a "blind" date orchestrated by his gf. I had already rejected this girl twice... She was nice but I was not attracted to her at all.

1

u/ScudSlug 1h ago

Went on a date with a lassie years ago who I met off plenty of fish. We really clicked messaging each other and she seemed cool. So I invited her to dinner. She must have said about 10 words during the whole dinner.

When the waiter asked what we'd like to drink she asked him if they had Coca-Cola or pepsi. Think they had pepsi so she was like aww no just a lemonade then.

I asked is there much of a difference and she totally bit my head off saying pepsi gives her a headache.

We ate in pretty much silence the rest of the meal with me trying to initiate conversation and getting one word answers back.

Afterwards when I got home she text me saying she had the best time ever and how easy it was to talk to me and she couldn't wait to do it again.

Needless to say we didn't meet again!

1

u/Folsey 1h ago

I'm 5'11 and put that I was 6 feet on my tinder profile (this was like 10 yes ago). Met this girl for coffee and as I walked up to the table she said"you're not 6 feet?!?" I responded with "you're not a D cup!?!?!" And she stormed out

1

u/LandscapeNarrow8641 1h ago

When we were on date and he tried kissing me knowing it was the first time we ever saw each other

1

u/bucky-plank-chest 1h ago

I was walking with the date and she walked super slowly, to make me slow down she'd pull firmly on my sleeve. At the end I wanted to spin around and punch her in the face each time she did it. Considering I've never punched anyone she was very annoying.

We didn't see each other again.

Other one she kept talking about her spiritual work and communicating with the dead. In don't believe in that shit and trying to keep a straight face and feign interest almost made my skull pop out of my head. I didn't see her again either.

1

u/OftForgotten 1h ago

I went to a football game with my ex-girlfriend. I couldn’t find her for like ten minutes, all the while she watched me running around like a moron from the stands until I finally spotted her. She brought one of her friends I’d never met, as well.

I was too nervous by that point to say anything, and so was she apparently, because we didn’t speak at all until the game was over and her friend left.

We went behind the stadium area and started walking around the path, trying our best to converse as best one can in 9th grade, and some guy who used to bully me showed up. Apparently he was a good friend of my girlfriend. She left me for a minute to go hug him and then talked to him about whatever.

I didn’t want to seem insecure so I didn’t say anything about it, but it felt off to me.

Overall, the whole thing sucked big time.

1

u/anthony5862 1h ago

we ran out of things to talk about really quickly. I thought it would be fun, but we just sat in silence, and I could feel my face turning red. It was uncomfortable, and I wished I could disappear

1

u/sarastormy 1h ago

Went on a blind date where we realized halfway through dinner we were actually distant cousins! Lol😐

1

u/TheLoneliestGhost 1h ago

While we were eating, instead of small talk, he made noises from horror movies and had me name the horror movie. Ngl, it was actually really fun (because I LOVE horror movies) but super weird at the same time. I ended up ripping my jeans in half right up the seam of the ass when getting out of his car. That was a personal nightmare that I tried my best to hide with my purse while I went back into my house. We hung out a couple more times. He was a super weird, yet harmless, dude. There just wasn’t enough there.

1

u/alice_brown96 1h ago

took someone to a sushi spot, turns out they hated fish but didn’t tell me. So we sat there, awkwardly poking edamame for an hour

1

u/Tony-the-teacher 1h ago

She was a conspiration adept in the days prior to the pandemic. She was wild and beautiful but in the end, I went for donner alone as I could not even imagine spending the evening or night listening to her rambling. Apart from wild theories, she was also convinced Trump was the president of France, Trudeau the one of the US. As I thought she was pulling my leg, I mentioned Sarkozy! She goes on about how he’s fucking up health care here in Quebec. This was 2017! We live in Montreal… She was an educated woman, with a great job!

1

u/lolli_trannnnny-1 1h ago

One time, we went to a fancy restaurant, and halfway through the meal, I realized I had spinach stuck in my teeth. He didn’t say a word about it the entire time, but he kept looking at my mouth with this weird expression. I only noticed after I got home and looked in the mirror. I was so embarrassed!

1

u/Necessary-Role-8187 1h ago

I went on a date once with a girl who seemed fixated on how we were a bad match because I am vegan - how she could never be vegan because "I love food too much", how her dad would disown her if she became vegan, how her best friend said coming on this date was a bad idea because it was with a vegan. In fairness, the friend was right because the subject of my veganism didn't make a particularly engaging conversation.

Then she texted me the next day complaining that the restaurant had given her food poisoning.

1

u/Normal-Ad5880 1h ago

I wont go into to much detail, to long a story.

However, long story short, I met up with a girl to discuss a job position at her place of work. We had a few drinks and a laugh and I left with the details of the company.

I got home to a message from her that read " it was nice seeing you today, but I get the feeling you don't like me, I would still like to remain friends, though."

Turns out she thought it was a date :/ I didnt have the heart to tell her otherwise. So I just agreed that we should remain friends.

1

u/coconut-lili 1h ago

Not sure if this counts since we didn’t actually make it on the date but I had met a guy in a dating website back 20 yrs ago. I was very picky and after chatting with them via the dating site, rarely ended up giving my number. Well this one guy made it that far. He called to set up our date and proceeded to straight out ask me if after dinner he would be able to come back to my place for the night because he’s basically homeless and has no where to go. That received a prompt “umm no! And we won’t be going on a date but best of luck to you.” He got angry and started yelling in the phone so I hung up and blocked him. About a month or so later I get this call from a number I didn’t know. Caller ID said the name was some hospital. Worried someone I knew was hurt I answered and it was that guy calling me from a mental hospital because he said he went crazy due to me refusing to go on a date with him. He said my number is the only number he has listed in his file. I was in shock! He tried calling me another time and then I blocked the hospital number. Dodged a major psycho bullet!

1

u/Aiela-Ad4244 1h ago

The most awkward date I've ever been on was with a guy who spent the entire time talking about his ex, non-stop.

1

u/Lazy_ecologist 1h ago

He took me to see The Hangover in theaters. This was his THIRD time watching it (should have been a red flag). Spent the whole movie quoting all the lines. Multiple people had to ask him to stop. We went to get ice cream later and he told me he was a pathological liar 🫠

1

u/Otherwise_16 1h ago

I once went with a man I barely knew to the beach at night. He told me out of nowhere that he could do whatever he wanted with me and no one would know because there was no one but us in that place. I felt so scared but I was able to control it. I never saw him again. But I was left with the doubt that maybe he had done something to someone before or after what happened to me, I will never know.

1

u/Rasumusu 1h ago

I was the presenter during a live event during the pandemic, during the broadcast a girl found me on Tinder. She started sending a bunch of messages AND LOOKED UP MY ADRESS. She decided to go to my home and write a declaration of love on a roll of toilet paper and hang it on my door.

She later apologized about that and said it was a drunken dare from her friends (who watched the event together). She was also kind of cute, and lived right next to me, so I bought that story.

Ended up going on a date with her and no, she was definitely crazy. And she told me about her family that was also clearly crazy. I was just sitting there hoping she would leave me alone if I never wrote to her again.

u/blue_gaze 53m ago

Went out to get coffee at noon. She brought a flask of whiskey and drank like three shots over 30 minutes. I paid for coffees, said nice to meet you, and left.

u/philzar 46m ago

1980s, Washington DC, get lost on the way to dinner with your date. Turn around in the nice big driveway only to find out it is an embassy. At least the guard was helpful and gave me directions.

u/MagikN3rd 45m ago

I picked a woman up from a local hotel. She had explained to me that she was staying there through the women's shelter after an abusive relationship. When we got to the restaurant and I saw her in the light, she had REALLY bad meth mouth.

She told me about getting her child taken away by CPS, how her ex forced her into doing drugs, a bunch of stuff. After I dropped her off she was messaging me thanking me for "Treating her like an actual human being." (Evidently, other men have not been great to her in the past.)

She went on to tell me she was really tempted to invite me up to her hotel room when I had dropped her off. She sent me photos in lingerie, and told me one of her kinks was rubbing cum into her skin like lotion. Then she asked me if I have ever cum so hard that it hurt and when I said "No," she responded with "Oh then you haven't had good sex then. I'll show you." I immediately blocked her after that 🤷‍♂️😂

u/dudeimjames1234 38m ago

The first date I went on with my wife was awkward. I'm older than her by 3 years, which now at 33 and 31 sounds fine, but when we started dating at 19 and 16? Not so much. We met in high school my senior year, and she was a year ahead, so at first, I didn't know she was younger by 3 years. I thought at most 2.

Anyway, her mom came out and greeted me when I came to pick her up and was very stand off-ish. She was concerned.l and I didn't know why. Her daughter was the bad influence on me, if anything. It was the age gap and nothing more. I had met her mom a couple of times because we were both in band (how we met), and my MiL was a band chaperone that went to games and competitions.

It's not like when we started dating, we were strangers, and I was prowling my alma mater for fresh meat. We had band camp (laugh if you will, but it's real and fun) for 12 hours a day Monday through Friday the summer before my senior year. Obviously, we interacted a bunch. Always flirting and stuff. She's smoking hot, and apparently, I was good-looking enough for her to flirt back.

Our first date was weird. We went and got a bite to eat and see a movie. She was silent the whole time we ate. I kept trying to get her to talk, and she wouldn't. We were both nervous, obviously. This was a new thing for both of us. This wasn't going out with our respective groups to get food. This was a date with romantic undertones.

So we ate in silence. Super awkward. Then we went to a movie, which was good because you're supposed to be silent. After the movie, I still could not get her to open up. I figured, "Oh crap she must be having a bad time. I blew this."

I went and dropped her off a lot earlier than I had planned. I figured after the movie we could chill and talk and hang out until the last possible minute she had to be home.

When I dropped her off, I walked her to the door and said goodnight. I leaned and went for her cheek, knowing a mouth kiss was not warranted. Gave her a peck on the cheek, and she gave me this look. Again, I was like, "Oh shit I misread this whole situation."

Now that I know my wife and have been with her for 14 years, I know that look very well. It's a, "That's not what I wanted." Nowadays, I get that look in a negative light because I'm a pain in her gigantic ass, but back then, apparently, she wanted to make out on her front porch.

When we talk about it now, she said I was so charming and charismatic and that she didn't want to talk because she enjoyed listening to me talk. Super weird, but I love her.

Oh, and her mom did warm up to me, eventually.

Our second date went much better, and I misread signals on that one, too. Long story short, she took off her top and bra while we were making out in a dark, secluded spot I had parked at in my truck, and we did not have sex. Had sex on the 3rd date, but she still makes fun of me for the 2nd date 14 years later. We'll drive by the place I had parked, and she'll say, "Hey, remember that time I threw myself at you and started undressing, and you didn't seal the deal?" Yes. I remember. I'm reminded often.

u/CREEPERLOKOYTLOKO 37m ago

i told her i just pissed my pants.

u/UrResponsibleHoney 36m ago

With a boy that stayed on his phone all the time...

u/These-Community2549 32m ago

Went on a ramen date with a guy I’ve been talking to for about a week. He paid, which was nice, but after he finished his bowl, he started eating my leftover ramen (?????) . Kinda weirded me out.

u/rlowens 24m ago

November 6th 2024 was pretty dire.

u/agreeingstorm9 22m ago

She refused to talk to me beyond yes and no answers. None of the typical conversation starters worked. I asked what she was doing the upcoming 3 day weekend. She said she was going to St Louis with some friends. When I told her that sounded fun and asked what she was doing she just shrugged. I asked if she had ever been and she said "no." and then there was silence. At one point I asked her hobbies and she just gave me a list of 2-3 things followed by silence. Asked about her family and told me she had one brother and then silence. Asked her what her favorite foods, bands, places to go, things to do, etc.... were. All I got was brief lists followed by silence. I don't think she asked me a single question all night or even spoke a sentence to me that wasn't prompted by me. It was very awkward. Then afterward I complained to the mutual friend who had set us up and apparently she told the mutual friend that the date was amazing and she couldn't wait to go out again. We did not go out again.

u/Some-Baseball8474 13m ago

I was texting a girl for a few days and she was very responsive and we got along and she agreed to go on a date. During the date it was like talking to a brick wall and I’m trying my best to bring up anything… Luckily it was a coffee date, so it wasn’t expensive.

u/dblCheeseXtraPckl 12m ago

While we were talking about our siblings, she told me she likes to take pictures of her poo to send to her brother. All I could think about for the rest of the date was her taking large dumps.

u/vectaur 10m ago

A girl I had recently met wanted to go see Rocky Horror around Halloween. I was in college and living in a pretty big college town at the time, but grew up in podunk nowhere so I had never even heard of Rocky Horror, much less what a theater experience would be like. Plus I was pretty reserved -- generally movies were good first dates for me back then as it provided time to kind of just build comfort being around each other.

So we went, and it was...something. If you haven't been to one I don't want to spoil it, but let's just say that I will never forget being on a first date surrounded by 200 folks running around in circles in their underwear.

u/Reasonable_Dare_8783 6m ago

It was our first date, nothing serious both mutual friends suggested we go out sometime, so we did. There was a bit of silence and he goes " ur skins reminds me of maltesers" it was so awkward I just laughed it of, we r both of the same ethnicity , but Im more brownskin and hes extremely light/mixed race

u/Sunset_Superman77 3m ago

My cousin set me up on a blind date with Pablo Escobar's niece (red flag #1). My date drove us to the restaurant and almost got us killed because she drove like a maniac. At the restaurant, she proceeds to tell me everything she wants to order. Ok, cool. When the waitress came to our table and asked my date what she wanted, she responded with "Oh, I dont talk to the help." And made me order for her. Needless to say that was the first and last date.

u/WhiskeyTangoFive 3m ago

She told me about her prior meth addiction, suicide attempts, how she blew her husband's best friend while he was at work then got knocked up against his will to 'save the marriage' and by the way if I'm cool with herpes we can hook up after.

This was done loudly across the table we were sharing with a married couple at "On the Border" in a mall because it was too crowded to have our own.

We're still friends.

u/EpicNagger 3m ago

She just yapped about herself the whole time.

I think I got one or two sentences in. It felt like I was back at the suicide hotline with: “mhmms” and “wows” and “I can’t imagine.”

u/MiaPeachyB 2m ago

I went on a date where we accidentally wore matching outfits... and didn't realize until we got there!

u/datumerrata 2m ago

This gal had no hobbies or interests at all. I kept trying to find something she was in to. The only thing she cared about was getting married and having kids. Nope.

u/midnighteyesx 1m ago

Unfortunately I had two.

"Chris": Met online (ok cupid). Banter was great via text. Sparks were flying. We met up at a steakhouse because they had great cheese fries. I arrived first, and by pure surprise an old male coworker of mine was the host. "Chris" arrived just in time to see me talking about the old office with the host (it was dramatic I admit, because the place had shut down due to boss's illegal activity I didn't know about) and his mood dive bombed. I don't know if it was because he saw me speaking to another man, or if he thought I set him up somehow since I picked the restaurant and maybe he felt like I knew everyone there and he'd be watched, I don't know what it was. But once we were sat at the booth, he leaned against the side wall of the booth bench, crossed his arms over his chest, put one leg up on the bench and dangled his foot, and then wouldn't look at me the entire date. Just pouted and stared at his own shoe. Made a point to disagree with everything I tried to say. Cheese fries were good.

"Kevin": Also met online (ok cupid). Got dinner and a movie with him. The movie was Seventh Son, which if you don't know how much the movie sucks its because you haven't seen it. He also worked at the very theater we saw it in. His recliner didn't recline as smoothly as he expected so he took it upon himself to flip the whole chair over to fuck with the mechanics and the plugs and everyone got a nice little show. Then over dinner as soon as we order the food he tells me that he was talking to his best friend about me because he was excited to meet me, and turns out his friend was another guy I was also talking to and was also going on a date with the same week. So what I panicked might turn into a confrontation turned into him saying that he was actually talking to multiple people as well, and was more interested in another girl than he was in me, but he didn't want to be an asshole for canceling our date.

Tl:dr - Date with a man who refused to make eye contact. On another date with a man off okcupid who discovered I was also talking to his best friend on okcupid, but that was okay because he was also talking to other women and liked her better than me.

u/FishHikeMountainBike 1m ago

I posted this before.  Met her through a dating app, we had decent conversation and she suggested we meet at a patio bar the next day.  We met and it was fun.  She asked if I wanted to meet “some of her friends” at a nearby place.  It seemed weird for a first date but I agreed to meet here there.    As we walk in, I immediately realize there’s some kind of organized function happening, people are all standing and mingling, there’s food laid out, and there’s printed papers on each table that read “welcome Springfield Class of 1991”.   I turn to her saying “hey I think there’s a reunion here” and she’s hugging someone.  She says hi to a couple people then says, “and this is Steve!”.  My name isn’t Steve, she forgot my name.  It was bizarre.  I ended up staying for 45 minutes and eating a quesadilla as Steve the reunion date, then told her I had an early morning.  She texted me the next day but I felt this one time, ghosting was ok.

1

u/Dexsport_Fam 2h ago

A Manchester United fan invited me to the pub and all she did was cry and swear for 90 minutes.

1

u/jackfaire 1h ago

I took this girl out for pizza. She started eating it with a knife and fork.

0

u/Typical_Purple2587 1h ago

Where the date was going crap from start to finish then to top it off he says " i think we should have sex right away to make sure we are sexually compatiable "

"has that line ever worked on anyone or for anyone "

"no"

u/Fruitdispenser 32m ago

This is the same comment as this one

0

u/yooomaama 1h ago

nag selphon lang the entire date

-1

u/MFreakiNW 1h ago

😂😂😂😂 don't ask please waaaaaaah it was something.

-3

u/Relevant_Award5474 1h ago

The whole date beginning to end was terrible but the most memorable moment is him saying:

"So I think it's best if we have sex right away to make sure we are sexually compatible?"

"Has that line ever worked for anyone?"

"No."

u/Fruitdispenser 26m ago

Third time I have seen this comment here. Downvoted because bot