FOR FUN – Tell an embarrassing date story

posted 1 year ago in Relationships
Post # 2
9021 posts
Buzzing Beekeeper
  • Wedding: Dorset, UK

Ha ha, I had plenty of terrible dates from online dating but the most embarrased I have ever been was I got set up by a friend on a blind date when I was at uni, so like 15 years ago. I was a poor student but figured I should probably make some effort, so I treated myself to a new mascara!


Anyway, we were a couple of hours into the date (which was horrible but was young and not confident enough to tap out! lol) and I finally went for a wee and noticed that my mascara was all down my face!!!! I have never had a mascara do that ever! I wiped off the smudges and went back to the table. I looked like an actual panda. 

Post # 3
819 posts
Busy bee
  • Wedding: May 2020

Third date with an ex. We had been friends for a bit and we worked together. I did not want to date him but everyone pushed for it and I knew he was in love with me. So the date went better than our previous two and we were ending the date. He kissed me and said “do you know how much I love you?” Which was nice but I did not feel the same. So I just said “you’re so cute” and left. 

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londongirl1988 :  

Post # 4
1475 posts
Bumble bee

Oh, so many from online dating adventures.  So I call 2015 the “Tour de Dudes” because I went out on probably 50 first dates, determined to claw my way out of the hole I’d dug myself after a really terrible breakup.  Buckle up, ladies…

Had gone out with this guy a few times, who was kind of strange but really cute so I kept at it, hoping things would really click.  Turns out he had raging ADHD and when he invited me over to his apartment to “hang out,” he really ended up talking incessantly for three hours without ever sitting down.  I finally sat on a stool because I got tired of standing awkwardly while he bounced from place to place.  When I finally said I needed to leave, he walked me out to my car and gave me a sweet kiss goodbye, then leaned down and whispered: “I love your perfume.  It’s the kind my mother used to wear.”  (He had told me on our first date that his mother passed away when he was young…) #bye

Got to one date and once I actually met my date, realized he was about 4′ 6″ tall.  Not.  Kidding.

Met one guy for lunch and after he told me a sob story about losing his job that week, I offered to pay for lunch.  I had heard from guy friends that online dating was brutal from the male perspective because they constantly thought they were being taken advantage of for free meals, and being an independent, modern woman, I thought I’d make a nice gesture.  When I said that, his face completely went blank, he said maybe two words the rest of the “date” and I never heard from him again.  So much for equal partners.

Met one guy for coffee and I’m not kidding, his hair made him look like a burn victim.  Really strangely patchy and just…odd.  He also had a tattoo on his forearm that said “YOLO.”  Again, not kidding.

Met one guy for lunch and could smell his B.O. from maybe 10 feet away, and he looked like the most awful version of his photos.  Sat down, tried to make it through a friendly lunch, knowing full well it wasn’t going anywhere, and saw a girl I used to work with.  She excitedly came over to our booth and slid in, and exclaimed “OMG is this your BOYFRIEND??”  Ughhhh.

Met one guy at a bar for casual drinks and realized immediately he was a total creeper.  He kept pressuring me to drink, even though I repeatedly and adamantly declined.  The female bartender kept throwing me looks of pity, as if to say “Do you need help?”  When I said I needed to leave he insisted on walking me to my car, even after I said it wasn’t necessary.  At the door to my car he said “You know what?  You’re too shy” and proceeded to grab me to try to kiss me.  I totally Matrix-twisted out of it and said “Um….bye” and he walked away looking ashamed.  I got an apology text from him later that evening and never heard from him again; this was probably my scariest experience.

One guy that I went on a few dates with (GOD KNOWS WHY – he was one of the first in this long and sordid string, so maybe I was in denial) really took the cake.  On our second date he proceeded to tell me that his mom put him in a mental institution when he was young, resulting in his modern day odd behavior, including paying $300 for a hand job from Craigslist a few years ago.  He also said “I don’t get into relationships with people I haven’t slept with because I don’t know if there’s a connection.”  Um, ok.  We were getting ice cream on date #2 and he put his arm around me and said “Just so you know, I’m going to kiss you when we get to your car.”  Cool story, bro.  Got to my car and I basically was like “Good luck to you” and left.  LOL.

ALL THAT BEING SAID, this is not to scare anyone off from online dating – but be prepared to wade through the muck to get to the good stuff!!  In 2016 I met my fiance on Bumble (he was my last swipe after giving it up again for a while) and we are getting married in October. 🙂 

Post # 5
156 posts
Blushing bee

One time I drove two hours on my own birthday for a first date with a guy I’d met online.  He had fed me a bunch of amazing details about himself, like he was in medical school and spoke 5 languages and was a rich youtube star (though refused to reveal his stage name).  Anyway, I arrive to the address he gave me, it’s a sketchy af motel.  He tells me his place is being worked on which is why he isn’t staying there at the moment and also his car “is in the shop”.  I should have turned around at the motel but god I was so desperate at the time.  So I pick him up and we go out for dinner.  He proceeds to full on flirt with the waitress right in front of me.  And it just got worse from there.  By the time the appetizer arrived I couldn’t contain myself, I told him I wasn’t enjoying the date and I wanted to go home.  He looked sad but I didn’t care.  I told him we could split the check since it wasn’t working out because I thought that was fair, but still expected a real gentleman to pick up the whole tab anyway – remember, it’s my actual birthday!  But of course he let me pay.  I still offered to drive him back to his motel.

Another, less traumatic memory, was a second date with another online guy.  He was pretty cool, it went well enough that we were making out in the backseat of my car.  But you know when you think you’re vibing with someone until you kiss them… He was loudly moaning the whole time, like it was a cheesy porno.  At one point I tried kissing his neck a bit and he was loudly groaning “oh maybeee, oh maybeee!”  Total turn off.  I didn’t get it.

And this one’s really my fault.  I went on a date with an actual medical student.  Very cute, very nice.  He told me he was studying to be a surgeon so I immediately thought out loud, “When you meet people do you wonder what their insides look like?”  He gave me a confused look and very flatly replied, “Uh, no.”  Tough crowd.  Anyway, I asked him if we could go on a second date and he turned me down!  I had never been rejected like that before.  So embarrassing.

Post # 6
72 posts
Worker bee

Online dating was the worst. In the two and a half years I was actively dating I only met 2 guys that I was interested in seeing more than once and both of them ghosted me immediately after we slept together. 

For the most part my other dates were bland but okay with the exception of a few real nightmares. 


– The guy who asked a lot of questions about me being an actress, mostly focusing on me having to kiss people for work. He couldn’t believe we would actually lock lips and thought it was an illusion. At the end of the date his line before he went in for a kiss was “well, since you’re a professional”. I awkwardly pecked him since he was coming right in and then bolted

– The guy who complained about his last online dating experience, where he went out with a girl a few times and she confessed to him that she had herpes. Apparently she cried and said she was so worried that she wouldn’t ever be able to find love because of it. When he was telling me this he was laughing, talking about how gross it was and moaning that he had wasted so much time on her

– The guy who spent the entire date talking about himself, his workout routine and his career ambitions. When I mentioned being an actress he said “that’s cool” and then turned the topic back to himself. He also made several racist jokes and complained that it is hard to be a straight man in online dating since so many women are looking to wear the pants in the relationship and just become lesbians

– The guy who spent the entire evening insulting me, grilling me about politics and bragging about how much money he had. When I told him I did not want to stay for another drink he told me I had to drive him home because he had taken an uber to the bar assuming we’d be drinking and now I “owed him” for that 

Post # 7
722 posts
Busy bee
  • Wedding: January 2021 - Dracut, Massachusetts

Not a first date, but funny story. I had gone on a few dates with this guy. Nice kid, but super dorky and just not my type. He lived in the same town my parents do and I happened to be at this awesome pizza place there with my two friends. He asked what I was up too and he came to meet us. My friend had ordered a TV on Amazon and we had to drive to another town to pick it up at like a FedEx location. He had a good sized SUV and we had been drinking so he offered to drive the three of us up there. My friend likes to rip farts on our other friend because, I mean if you knew him, he’s just fun to fart on. Anyway, so she gets on his lap in the backseat of his SUV and lets one rip on his leg. It smelled SO BAD LOL. She stunk up his entire car!!! It was the best. That was the last time I hung out with him- on my decision!

Post # 8
5230 posts
Bee Keeper

This was my freshman year at college. I was home on Thanksgiving break and some people that I used to babysit for asked me if I would accompany their friends son that night. He was German and didn’t know the area. I said ok.

So I met up with him and asked what he wanted to do. Have a beer, he said (how Gernan). So we went to a bar I knew. Now technically I was not allowed to drink, being underaged and I was a bit nervous of this. The law had changed recently from 18 to 21. But somehow I got served which sort of amazed me. I got carded up to the age of 36, so I don’t know how i got through. 

So we get our drinks and i go to sit down on a stool. Now as i said, it was my freshman year at school and I had gained the freshman 10. The jeans I was wearing were pretty tight and when I sat down they ripped right up the middle – a long rip. Joy. So there I was, trying to make conversation in a foreign language and the whole time thinking about my ass being on view the minute I got up from the stool. But I did get up, ended the date and sprinted for the door, hoping no one noticed my underwear. Yeah, right.

I lost the weight the next semester.

Post # 9
1718 posts
Bumble bee

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coffeetime2020 :  haha omg did we date the same guy?!! My most embarassing date was with a guy who told me about a girl he dated who confessed to him she had herpes while they were at his apartment. He suggested they go on a walk outside so he could get her out and dump her without her being in his place. Honestly he should have stayed with her. If she was willing to date this guy and actually liked him he should have clung to her like the plague lol. 

That guy was AWFUL. Just completely clueless. I don’t even remember his name anymore but wow was he a piece of work. We had 2 dates. I was trying to date at the time to get over a breakup so i went on a 2nd date when I knew he was weird already. Second date he proceeded to get SUPER wasted (9 or 10 long island ice teas over the course of 4 hours) He CRIED and told me he just wanted to find someone and get married and have kids but women are “so mean” and only care about finding someone better, grass is always greener mentality. No taking accountability for his behavior and how he might have scared these women off. No, it was all about how women lead HIM on. LOL. It was HILARIOUS. 

I texted him it wasn’t going to work out and wished him the best, super nice. He sent me back 2 PAGES of text about how the dating world is tough and he hopes that i will find someone before I end up like him all frustrated and jaded by the dating world. LOL. I kinda hope he finally figured out he was the problem and worked to be a better person but who knows. 

THe other embarassing date was the one with a guy who had such a thick irish accent that I couldn’t understand all that he was saying. I would say ” oh yeah, cool.” because i didn’t understand, and he would stare at me all strange because I clearly didn’t respond correctly to what he said hahahha. 

Post # 10
236 posts
Helper bee
  • Wedding: September 2018

I had just moved to a new city and was trying to make friends, and someone in the new “group” I was hanging out with introduced me to a mutual acquaintance. He was really cute and had just gotten a great job after getting out of the military, so I assumed he had his life together. 

He asked me out, but wanted me to pick him up from a Walmart parking lot. He claimed it was close to his work and made some excuse about his car being in the shop. He asked me for a bar suggestion and I drove us to a fun dive bar thinking we could hang out, talk, and play pool.

Immediately after getting into the bar, he started complaining that it was “too expensive.” Keep in mind that this was $1 beer and free pool night. I was lonely in my new city and desperate to meet new people, so I mentioned that I had a bottle of whiskey in the trunk of my car (I had just bought it for a “whiskey tasting night” that I was going to the next day). He proceeded to drink half the bottle while sitting in my car and complaining about his life, then lunged at me and tried to sloppily kiss me while slobbering all over me. I was stone sober since I had to drive, and I was horrified.

Turns out he suffered from an alcohol problem and wasn’t allowed to drive because he had gotten multiple DUIs and had an approaching court date. He had lost his great job and was living with his mom, which is why he didn’t want me to pick him up at home.

He proceeded to call me repeatedly over the next few weeks/months at all hours of the night, crying and begging me to invite him over so he could “snuggle with me in my bed.” I declined and didn’t see him for several years. I ran into him a year or two ago at a karaoke night and said hi to him politely, after which he stormed over to my table and told the people I was with that he was the “best thing that ever happened to me.”

Post # 11
817 posts
Busy bee
  • Wedding: June 2019 - Tacoma, WA

My most embarassing date story, off the top of my head, was the time I literally didn’t realize I was on a date until much later than I’m proud to admit.

I knew this person as part of a wider friend circle. So, we weren’t close friends by any means, but we knew who each other was by name and chatted occasionally if we happened to meet up at an event or larger hangout, etc. Anyway, one night she suggests we go grab dinner and drinks sometime, and I agree. This was after we had chatted at a bar one night when a bunch of us were all hanging out, and our convo was interesting, so I just thought of it as a “let’s continue this conversation over dinner and drinks sometime!” But, apparently, she liked me and was asking me on a date.

A few important facts to know: One is that I’m the kind of person who has to be told outright if someone is interested in me, or I will literally never think that’s the case. I don’t pick up on hints or cues. I always just assume people are being friendly. Second, is that in the lesbian dating world, it really can be hard to know what’s a date and what’s just hanging out as friends. And, third, this person was super sweet, but was not someone I was attracted to on any kind of romantic/sexual level.

Ok, so the evening comes around and she picks me up at my place to take me to dinner. Parking in my city is rough, so when she offered to pick me up, I figured it was a good way for us to only need to park one vehicle. When we talked about doing dinner and drinks, I told her to pick a spot, so she did – a fancy place overlooking the water. First we stopped at a local bar for a few drinks, then we walked over to the restaurant. She paid for the drinks, which I thought was nice, but didn’t think much of it. I was seriously nervous about the restaurant, though, because it was quite a bit outside my budget, but then, I HAD told her to pick a spot and I didn’t want to disclose my lack of funds, so I just kept quiet and did frantic math/budgeting in my head while we walked. She opened every door for me, which I thought was sweet, but again, didn’t really think much of it. I open doors for friends all the time.

We get inside and she’s made reservations for a specific table at a window. The view is obscenely beautiful. We order some drinks and start looking at the menu and she asks me what I think looks good. I’m looking for the cheapest thing on the menu when she suggests a somewhat expensive dish she loves and insists that I “have to try it” so I go ahead and order that (it did look really good), while panicking still in my head about what this is going to cost me.

We enjoy dinner and a couple of drinks and have a lovely conversation. She’s asking me about what I do for work, about my family, what my passions are, etc., the kind of stuff you ask someone, oh, I don’t know…ON A FIRST DATE…but I’m oblivious still. The check comes and I politely ask the waiter to split it, but she takes the check and kind of smirks and says “you’re so sweet, but I’ve got this” and pays the check.

After dinner, we continue our conversation as we walk along the waterfront back to her car. She’s telling me what a great time she’s having and that she hopes we can do this again soon and how hard it is to meet people she really ‘connects with.” I agree we should do it again soon, tell her I’ve also had a lovely time, and she moves and proceeds to give me the most awkward hug of my life. Looking back, it’s clear she was trying to kiss me but I made the hug move instead so she rolled with it.

She drives me back home and walks to my door with me. Cue a few awkward moments outside my door where she’s just kind of looking at me with this expectant look on her face as we make smalltalk, like she would like to hang out longer, but I’m kind of exhausted at this point and it’s super late and I’m not really feeling up to hanging out even later (because I still for some reason think this was just a friendly hangout with a new friend), so I thank her for the lovely evening and tell her next time drinks and dinner are on me, give her another awkward non-kiss hug move and say goodnight.

Ya’ll, it wasn’t until I was telling a mutual friend a few days later about our hangout and what a good time we had that I finally understood – when she said “Dude, you do realize that was a date, right? She’s been into you forever and finally had the courage to ask you out!”

Looking back on the evening, it was pretty freaking clear, but apparently not to me. I was so embarassed that I hadn’t picked up on all the cues that I couldn’t even face her again for the longest time afterward.

Years later and we’re fairly good friends now, and we still laugh about that time we went on a date that I didn’t even know was a date until literally days later.

Post # 12
967 posts
Busy bee
  • Wedding: July 2019

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londongirl1988 :  So not my story but my fiances.

He said once on a first date a girl told him she was tracking her ovulation! Like WTF?? LOL.

Fiance and I got engaged after a year and he wants a baby ASAP so hes not anti commitment/kids at all but that totally weirded him out.

Post # 13
72 posts
Worker bee

This video has floated around the internet for 10 years now so many of you have probably seen it. I thought I would still share anyway. 

This is an actual voicemail left for a woman by a man she had given her number to

Post # 14
578 posts
Busy bee
  • Wedding: September 2018 - City, State

Y’all this thread is killing me XD I’m steeling myself to jump back into the dating scene and all these stories are NOT. HELPING.


I took the same approach as some of y’all a number of years ago before I met my husband (treat it like a numbers game, or a Dude Deluge as some friends called it) and met some real winners. Most guys were ok but just not the right fit, but some … let’s just say I wouldn’t be that shocked to see their mugshots on the news some day. One guy was being boarish at dinner, but I thought I could just suffer through and be polite. I guess I looked pretty unhappy, though, because one of the waiters came over several times asking if I needed anything and giving me a really significant, “Do you want help??” look. I told him it was fine, we were just finishing up, and the waiter went to get the check. My date picked up the knife off his plate and said, “If that _racial slur_ gets in your face one more time I’m going to put him in his place.” And then he LAUGHED. (Oh, dating in the South!)

He said it loud enough that people at adjacent tables heard him and turned to stare. I was mortified. I paid the whole check, cash no change, just to get out of there ASAP. I literally got up and walked out without saying anything to the asshole, who followed me onto the sidewalk asking “What’s the rush? I’m having a good time, can’t we have one more drink?” over and over.

I told him straight to his face that I didn’t like him, I found his comment awful, and there was a snowball’s chance in hell of us ever going on another date.

He got INCREDIBLY aggro, told me he didn’t come all the way into downtown on a Saturday night and pay $30 for parking just to get “shot down by some fat skank,” and said he “deserved at least a blowjob” for the effort. I started cackle-laughing in the middle of the sidewalk and told him to go suck his own tiny dick. Last I ever saw him, he was yelling “DON’T YOU WALK AWAY FROM ME BITCH!” at my back while I strode off down the sidewalk. Sorry about your fragile masculinity, dude. A trio of young guys asked if I was ok and wanted an escort to the bus station, which I appreciated, but I was fine. 

Glad I made it out alive.



In much more light-hearted stories, I once went on a date with a guy who claimed to be a regional dance champion in his hometown. I’m not a great dancer but I’ve always wanted to try, so he offered to take me to a very chic tango club in a nearby city. However, every time we planned, he either cancelled or said he “wasn’t feeling it” and pushed me to do something else. Ok, cool. By the third date I was getting a little suspicious, so he took me … turns out no one there knew him, he didn’t have the “in” he claimed to, and – SURPRISE! – he DID NOT KNOW HOW TO DANCE AT ALL. He pulled me onto the floor and tried to do the middle-school sway while shoving his tongue down my throat. I was, again, mortified. There was no fourth date, and the racy dancefloor-inspired lingerie (think: red, frilly, lacey, a little flamenco-y) I’d worn for the occasion went unseen. 

Wild times.

Post # 15
386 posts
Helper bee

Oh I can never live this one down.

I was 16, at our high scchool dance, and I had on a huge poufy skirt with a tailored jacket and little booties. Yes I styled it myself, straight from the Mary Poppins fashion line, although I didnt realise at the time who it channeled and was pretty pleased with my look. My friends btw are wearing nice little dresses or short skirts.

So all the teen hormones are all over the place and girls and boys are eyeing each other. Everyone knew who the cutest guy was, lets say his name is Tony. He was from a well known family in our town, sporty and VERY cute to boot. I was minding my own business when, really early on, he comes up and asks me to dance.

I think now that I was just a warm up, but at the time, things were compounded by me being shy and not expecting attention from any guy, least of all him.

First off, I couldnt  believe it was Tony I was dancing with. We couldnt hear each other and had to do the mouth to ear thing a few times. We had major eye contact and I felt serious little butterflies as this cute guy asked me stuff about myself. 

Anwyay, whilst chatting, I suddenly gestured, a little too wildly, at the floor to emphasize a point I was trying to make and then I felt a thud on my hand as I raised it across my space. The flashing strobe lights and loud music meant I couldnt see or hear anything so I couldnt understand what exactly my hand had made contact with, really hard, (I could feel the dull pain ages after) until I saw Tony standing still in front of me, and I realised I’d just clean whacked him across his pretty face.

My hands flew up to my own face in horror. I apologised profusely and to his credit he was very kind and sweet about it. A joke at this point may have saved the situation, but I was too mortified and inexperienced to come up with that.

Nonetheless, in an instant, the moment was lost. We had been enjoying flirting and some serious chemistry and my hand completely bitch slapped the fun out of it, and at the end of the song he took me back to my seat and thanked me for the dance (possibly to head for some ice).

I still flame up in sad shame when it comes back to me. At that dance, Tony met and went on to date a really cute girl in my year for a very long time but they broke up and I never saw him socially again.  I may have been married to Tony today if things had turned out differently. Oh well. 

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