Current Events > Describe your worst / most awkward dates

(+) Yeah! (+)

I wanna hear cringe CEmen dating stories

---

I went out with a chick a few days after my aunt committed suicide. She offered to have someone murder my aunt's boyfriend. She had another dude there. She went home with him. Haven't seen her since.

DDirtyDastard posted...

I went out with a chick a few days after my aunt committed suicide. She offered to have someone murder my aunt's boyfriend. She had another dude there. She went home with him. Haven't seen her since.

Oh my god 0_0

---

This was an on again, off again relationship with someone I'd known since high school and saw around parties and other social activities. We decided to try "real" dating after a year and I decided to be sober for that. She said she wanted to go to Olive Garden and in one of the few times I've ever thought about GameFAQs away from actively being on the site (except when I was like 14 and dreamed I got banned), I thought about that meme from the food board and laughed.

She got defensive and I scrambled to play it off. I don't think I'd ever even eaten there at that point, plus I was trying to lose weight at the time and not wanting a bunch of greasy pasta crap, but she seemed genuinely excited about it and I felt bad about making her self-conscious, so I tried to feign enthusiasm.

This was during the first time I tried to lose weight and I wasn't counting calories or anything, just doing at a glance portion control. I was seriously under-eating and miserable as shit, so I was looking through the menu trying not to bitch about everything. This was also about the time my alcoholism started ticking up and I really wanted a glass of wine but I knew I'd overdo it. Upon the waiter's recommendation, I got a noodle and marinara dish that I think was maybe like 520 calories. It was just noodles with what I'm pretty sure was canned diced tomatoes on it with a whisper of olive oil. It was a horribly unbalanced meal with no protein and utterly unsatisfying.

To make things worse, my partner was even bigger than me and really enjoyed her food. She got some big ass meaty, cheesy thing that at the time was really messing with me. She started doing these exaggerated enjoyment sounds that I'm not sure were entirely exaggerated, trying to tempt me but I stuck to my guns. She drove so she didn't get wine but she did talk to the waiter about the wine menu to mess with me some more. I tried to pace my meal and one bread stick I allowed myself so I wouldn't be just sitting there while she was eating but I couldn't help it and ended up finishing while she was half done. She finally finished then ordered freaking dessert, this chocolate beast that came with two forks.

I didn't explicitly complain but I was aggressively sober and hangry so I guess my poker face didn't hold up and she said she could take it home and eat it. I was just like, nah it's cool but she wanted to go anyway.

I don't think it was THAT bad but I was also incredibly oblivious back in my drinking days and the mental strain from my shitty weight loss plan made it a lot worse. The night got a lot dumber/crazier because of how the date went but I look kinda bad in that so I won't share that part.

That's probably the worst one, that I can remember at least. When I started trying to meet new people, there were a couple of bar dates where I was good and drunk before even getting there, so I talked to my date for like ten minutes before the rolling brownouts started. Neither lady even bothered talking to me again after those, so I'm left to guess that they did not go all that well.


---

date got blackout level drunk and starts dropping n bombs at a bar.

---

We went to see 500 Days of Summer.

---

She farted loudly on the ride home in my car, and it stunk. But I laughed for a solid minute whilst gagging, and I ripped some shortly after before we made love. Keep in mind, this was date number two.

---

I was hanging out with this girl. We went out to eat, watched a local band play. On the say home she wanted to stop and get some beer to take home. When we got home she said she was calling it a night, in reality she had another guy come over and they shared the refreshments I paid for.
---

Sure. It wasn't a date.

---

One time I asked a girl Id been courting out to dinner after hooking up a few times at work in the lift.

Anyway, turned out she had a much older BF and she brought him along and had to explain what was going on. Very awkward. Dude was cool about it and bought some art off me. I cringed tho

---

I went to a date with a girl I met off OKCupid.

She was *much* larger than her profile picture suggested. She wanted to talk about star signs. We went for a walk, she ended up somehow reading my tarot in a park. She was very strange, even by my standards.

I ghosted her.

A few months later she sends me a text message saying shed accidentally signed me up for AA

---

I was on a date on a gender-flipped Halloween night out, dressed as a sexy witch, she was dressed as Dracula. A guy at the bar, who was just there to watch rugby and wasn't participating in the gender flip, slapped my ass. I didn't know what to do, so I just shouted "Daddy, no!" and he and all of his friends laughed at me.

The date went well otherwise, but that moment was so awkward I still cringe over it.

---

I mean I posted it the other day. Took his dick out while we were watching Wall-E repeatedly even after I was like I don't want anything sexual with you.

Oh wait I have another. I was 18 and seeing a guy. Now I knew his parents were a little more sexually open with their kids (left condoms and porno mags on his bed). We are at his house and decided to go rent a movie, we picked "Young People F***ing". Now we get back go downstairs to watch it and his mother is doing yoga. She's like oh I'm almost done then you can put it on. After she's done we put it in the player as she's cleaning up and we sit on the couch, then...she's calls his dad downstairs to come watch the movie with us. Us? They are going to watch it with us? Yup they were, and they knew what we had rented too. His dad makes comments through the whole movie like, "Aw son! Never let a girl do that to you!" And I'm stuck there for the whole movie until it ends and I can quickly get out of that weird situation.

---

i was 19, met my g/fs mother for the first time, we ate a local restaurant.

halfway through mom looks very weird, keels over off her chair, and vomits while lying on her side while flapping a bit, like a seal.


---

SamsungGearS2 posted...

She farted loudly on the ride home in my car, and it stunk. But I laughed for a solid minute whilst gagging, and I ripped some shortly after before we made love. Keep in mind, this was date number two.

Reminds me that my dad farted on my mom's head on purpose on their 3rd date. Knowing the bitch now, she deserved it.

---

I went on a first date just to get a drink with someone I met on okcupid. Her first name was unique, so a day or so before the date, I had typed in her name to facebook out of curiousity and found her easily. Not to stalk or anything, just to make sure I wasn't really being catfished. She had her features pretty limited, but her place of work was listed and it's a pretty reputable company with one downtown building, but for privacy reasons, let's just say Wells Fargo.

Date seems to be going solid as far as first dates are considered. Conversation's going well more or less. She's talking about something random, like what things there are to do in St. Paul or something like that, I don't remember. It was loud in there, and she kinda trailed off the end as the volume dropped but she was clearly ending her sentence. I didn't quite catch the last word or two she said, but I thought she said "Wells Fargo," so I leaned in a bit and said "Wells Fargo?" (you know like how you repeat something you thought someone said just to make sure you heard them correctly).

Well, it definitely was not what she said. And the look in her eyes DEFINITELY had me thinking "oh my fucking god why did I just basically admit to finding her online" (by basically telling her I know where she works).

Aaaaand yeah. From there it was pretty hard to keep the conversation going. She was noticeably more withdrawn, less energetic with her speech, just across the board turned into a massive bummer. Needless to say, date number two did not take place. Although I think I may have avoided a potential fire because she talked about her "best friend and also ex boyfriend who lives in Wisconsin" a lot. Definitely enough to stand out to me. And like I have zero qualms about talking about exes in passing; we're all adults, we've had past relationships, it's fine to hear about it. So for it to stand out to me is pretty damning.

I also did think it was strange that she let me give her a ride back to her car -- I had a good parking spot and so even though I thought the date would be over the moment we left the bar, I still casually offered to take her to her car and she accepted.

Still. Kicking myself to this day because I'm forever engrained in her head as a creepy-ass stalker who found out where she works before we even met.

---

I went on one date where the woman I was with was really open and made me feel free to act as if we had known each other a long time. However she kept going on about her exes including one who od'd about a year before our date. Despite this we tried to connect for a second date but then she started entertaining notions about moving to South Carolina to be with another ex and then I realized I had to move on.

---

Olivia2 posted...

Oh my god 0_0

I really liked her too. She diarrhea'd my bed twice. I was cool with it. She watched too much Netflix though.

Dumb lunch with bad conversation. She was really good at repeatedly asking me how Catholic I was, and not very good at any other topic of conversation.

---

Girl suggested we get a bag of cocaine during our first date. I agreed because I'd enjoyed coke in the past and like fun people. But it ended up giving me both ED and high anxiety and the date went from really good to really shit in a couple of hours. Not gonna mix drugs and dating again

---

never had one

---

haloiscoolisbak posted...

Girl suggested we get a bag of cocaine during our first date. I agreed because I'd enjoyed coke in the past and like fun people. But it ended up giving me both ED and high anxiety and the date went from really good to really shit in a couple of hours. Not gonna mix drugs and dating again

According to my mom my dad asked her on their first date if she was into coke. Hearing some of the things she's said about her and my dad's early dates it's a miracle me and my brother exist at all.

---

PatrickMahomes posted...

I went on a first date just to get a drink with someone I met on okcupid. Her first name was unique, so a day or so before the date, I had typed in her name to facebook out of curiousity and found her easily. Not to stalk or anything, just to make sure I wasn't really being catfished. She had her features pretty limited, but her place of work was listed and it's a pretty reputable company with one downtown building, but for privacy reasons, let's just say Wells Fargo.

Date seems to be going solid as far as first dates are considered. Conversation's going well more or less. She's talking about something random, like what things there are to do in St. Paul or something like that, I don't remember. It was loud in there, and she kinda trailed off the end as the volume dropped but she was clearly ending her sentence. I didn't quite catch the last word or two she said, but I thought she said "Wells Fargo," so I leaned in a bit and said "Wells Fargo?" (you know like how you repeat something you thought someone said just to make sure you heard them correctly).

Well, it definitely was not what she said. And the look in her eyes DEFINITELY had me thinking "oh my fucking god why did I just basically admit to finding her online" (by basically telling her I know where she works).

Aaaaand yeah. From there it was pretty hard to keep the conversation going. She was noticeably more withdrawn, less energetic with her speech, just across the board turned into a massive bummer. Needless to say, date number two did not take place. Although I think I may have avoided a potential fire because she talked about her "best friend and also ex boyfriend who lives in Wisconsin" a lot. Definitely enough to stand out to me. And like I have zero qualms about talking about exes in passing; we're all adults, we've had past relationships, it's fine to hear about it. So for it to stand out to me is pretty damning.

I also did think it was strange that she let me give her a ride back to her car -- I had a good parking spot and so even though I thought the date would be over the moment we left the bar, I still casually offered to take her to her car and she accepted.

Still. Kicking myself to this day because I'm forever engrained in her head as a creepy-ass stalker who found out where she works before we even met.

That's literally pretty normal though?. A lot of people do it, you are meeting a stranger after all. I'd have addressed it by saying, 'oh whoops sorry I had a cheeky stalk before our date' or you could have said she came up as a suggested friend and you had a quick peek

Like it shouldn't be taboo to talk about imo.

---

haloiscoolisbak posted...

That's literally pretty normal though?. A lot of people do it, you are meeting a stranger after all. I'd have addressed it by saying, 'oh whoops sorry I had a cheeky stalk before our date' or you could have said she came up as a suggested friend and you had a quick peek

Like it shouldn't be taboo to talk about imo.

Yeah hindsight being what it is, I definitely have replayed what I should have said a million times. But in the moment I immediately went from cool and collected to panicked as fuck.

It was definitely a salvageable situation but I did not salvage it whatsoever due to sheer panic.

But in general I agree, a little advance prep isn't a bad idea IMO. Truth be told, it's a testament to how well our conversation was going that we didn't even get to talking about what we do for work. If we had gotten there and she had already said Wells Fargo in conversation, then all would have been fine.

---

SamsungGearS2 posted...

She farted loudly on the ride home in my car, and it stunk. But I laughed for a solid minute whilst gagging, and I ripped some shortly after before we made love. Keep in mind, this was date number two.

Xavier_On_High posted...

I was on a date on a gender-flipped Halloween night out, dressed as a sexy witch, she was dressed as Dracula. A guy at the bar, who was just there to watch rugby and wasn't participating in the gender flip, slapped my ass. I didn't know what to do, so I just shouted "Daddy, no!" and he and all of his friends laughed at me.

The date went well otherwise, but that moment was so awkward I still cringe over it.

These are awesome and I like you both.

---

Matched with a pretty hot petite Spanish girl on tinder. Talked quite a bit. Probably for a week before we met. Went out for lunch on campus. We planned a date to the state fair

entiee thing was incredibly awkward because how awful the fair was. Overpriced everything. Lines took hours.

I planned to make a move on the Ferris wheel. But nah, a dumbass family decided to join us on the same cart so it wasnt just me and her and it ruined the mood. They were supposed to go in the cart behind us but they didnt understand cause they didnt speak english

didnt see her after that date lmao.

oh yeah, funny thing is I was shopping for my now current girlfriends birthday present at LUSH. And she turned out to be the girl helping me find a product lmao. I dont think she recognized me though cause we both had masks on cause covid

---

Flawless_Lee posted...

then...she's calls his dad downstairs to come watch the movie with us

Do you think she did this so you couldn't hook up? I could see why watching porn with your bf's parents would be awkward. Jeez XD

---

I also have where I was invited to Easter to meet my boyfriend's parents at the time. I was invited at the last minute possible, I wasn't too ready. First thing I notice when I walk in is one wall dedicated to iron crucifixes, did I mention it was Easter? Correct his brother out of habit and said that Irregardless wasn't a word, that was awkward. Whole day was so awkward, I was 8 months old than him and his dad called me a cougar. Boyfriend was in a foul mood the whole day for some reason and we broke up 2 days later. I was like wtf why did you last minute invite me to meet your parents then, to torture me?

---

Olivia2 posted...

Do you think she did this so you couldn't hook up? I could see why watching porn with your bf's parents would be awkward. Jeez XD

Naw I don't think that was it, I think they just thought we were renting a video for everyone. It wasn't porn, just an 18A comedy movie.

---

Flawless_Lee posted...

I also have where I was invited to Easter to meet my boyfriend's parents at the time. I was invited at the last minute possible, I wasn't too ready. First thing I notice when I walk in is one wall dedicated to iron crucifixes, did I mention it was Easter? Correct his brother out of habit and said that Irregardless wasn't a word, that was awkward. Whole day was so awkward, I was 8 months old than him and his dad called me a cougar. Boyfriend was in a foul mood the whole day for some reason and we broke up 2 days later. I was like wtf why did you last minute invite me to meet your parents then, to torture me?

Kinda reminds me of when I was hanging out with an ex and I knew I was going to breakup with her soon, and her parents invited me to celebrate her sister's graduation. I declined, knowing I was about to breakup with her. I think I broke up with her 2 days later as well.

---

Flawless_Lee posted...

Naw I don't think that was it, I think they just thought we were renting a video for everyone. It wasn't porn, just an 18A comedy movie.

Oh XD the title could've fooled me :P

---

I took a fat chick on a date once, she had a great personality, and we had a similar sense of humor.

She wanted to eat Chinese, so we went to a local buffet that's really good. It was a Sunday, and on Sundays they served crab legs. I've never seen someone wolf down that many crab legs in my life, she ate a truly unhealthy amount. Not only that, but she stopped talking, or conversing, and things got really awkward. She went back up for her 4th plate of crab legs, yes #4, not counting the 2 plates of other stuff she had.....And a little Chinese guy wearing a culinary/chef outfit walks up to her in the buffet line and says in a deep Chinese accent "All you can eat, doesn't mean you can eat it all!".

I was super embarrassed, humiliated even. I felt really bad, because this was a place I'd eat at regularly, like at least once a week, so I double-paid for mine and her buffet expenses, it was $12 a piece, and I gave them $50. And I don't fault the little Chinese Chef for getting mad, because some fat chick eating 4 plates of crab legs, is just inhuman levels of gluttony.

---

She gave my contact info to the Vector Marketing Cutco knives people and they called me for weeks.

---

Oh yeah I also went on a date with a chick who told me she would pay me ten thousand dollars to marry her for a green card

Honestly it wasn't awkward or weird really. Caught me off guard for sure but it was interesting enough to talk to her about it. She didn't say anything about it online because she didn't want to put anything like that in writing.

But it was one of those things where I knew there wasn't going to be a second date so I just dropped all pretense and started asking some of the most personal questions (since that's kinda where the conversation was leading anyways, but on a standard first date, I would pull back for risk of scaring her away).

---

This girl Id met on a dating app wanted to meet after months of talking. Went to visit her (mind you, we both are foreigners in another country) and first thing she did was hide in an alley and giggle. We finally sent to eat, and sent to karaoke. She got mad because I chose songs that werent in English (country isnt an english speaking country, btw). Whatever.

Got coffee, it was better. Then she wanted to get a hotel room. I asked her jokingly, why, and she said she just wanted to talk. Haha yeah whatever. She sId she was gonna ask a hotel clerk about prices, I played along.

she dissPeRed for two hours. Finally got a text from her saying she went back to her apartment to clean it???? Whatever, She eventually came back and had some dumb excuse that I cant remember.

To this day, I still dont know what was up with her. Ironically, we are pretty good friends now. I bring it up as a joke sometimes.

---

Girl asked me if I wanted to go and meet her parents, after the date. Wtf. I barely knew the girl.

---

I've never actually had a date, but there was one woman I matched with on okcupid. That was a disaster and a half.

When we matched, she immediately told me she was only looking for friends and nothing more. I said that was fine, as I also needed friends and thought it'd be a good way of meeting new people.

Then one night at work she just shows up. I hadn't even told her where I worked. She had taken my picture from my profile and showed it to everyone she knew until she found people that knew me. She gathered all kinds of info on me, like where I work and where I live. She told me that she had gathered my info that way and figured out I'd be at work that night. She even brought me a hat that she had knitted for me, and candy... So, obviously I was caught off guard, my anxiety kicked in. It was awkward, and weird, and I'm sure she could tell I was put off.

Anyway, she continued randomly popping in at work on my shifts. At this point she'd also figured out that I was a virgin(by me saying I'd be uncomfortable watching sex scenes around other people no less).She started teasing me over that fact. Kept telling me about who she had slept with, and which of the guys we both knew were better... It really bothered me, a LOT. She was still quite clear that she wanted nothing of the sort from me though.

After a while, she told me of a dirty dream she had about me(which admittedly was the hottest thing that's ever happened for me). Also, she decided that when she wanted to have a second kid, that she wanted me to be the father(I want a kid so badly too). At that point I reluctantly asked for advice here, and was told to cut things off with her. I was still entertaining the idea of possibly asking her to help me get some experience, but the consensus was that it'd be a terrible idea.

At this point she met back up with one of my brother's friends. She kept telling me about how well he fucks. Even one night telling me she had just came straight from his place and getting fucked to see me at work. Mentally, I couldn't handle much more so I bit the bullet and cut her off.

I don't know what she wanted from me. No matter what she insisted that I had no chance with her outside of friendship. Then kept implying that she wanted more, before teasing and going out and hooking up with someone else. Idk if she just liked humiliating me, or what, but that whole experience was terrible.

---

There was one time I was on a date and didn't know it was a date. I met the girl at a recruiting event for my fraternity (it's a co-ed engineering fraternity) and I thought she was interested in joining because that is literally what she said at the event. And then dumbo me missed the next hint where she said let's grab dinner together at a campus cafeteria. At dinner we talked about the frat and a bunch of other things, no biggie I thought it was small talk.

So after that I brought her to the frat and figured I should let her talk to other fraternity members to decide how she liked the place. Didn't think how odd it was that she was sitting by herself for about an hour until the next day. Never heard from her again.

---

I picked a girl up from her house and her mom came out to the car and asked have you given yourself to Jesus Christ?
I was so shook I said an all too honest answer: I did when I was little but we didnt get along
She told her daughter to get out the car, she refused, her mother then started shouting at God as I backed out of the driveway. When we got to the restaurant the date told me I was rude for eating before saying grace.
I said I was hungry. Hell forgive me though.
She was offended and I drove her home immediately after we ate.

SwiggitySwoogit posted...

I picked a girl up from her house and her mom came out to the car and asked have you given yourself to Jesus Christ?
I was so shook I said an all too honest answer: I did when I was little but we didnt get along
She told her daughter to get out the car, she refused, her mother then started shouting at God as I backed out of the driveway. When we got to the restaurant the date told me I was rude for eating before saying grace.
I said I was hungry. Hell forgive me though.
She was offended and I drove her home immediately after we ate.

This was very amusing lol


---

bump

---

chick showed up loaded and at the 2nd pub we went to, she hitched up with some other dude there. i explained the situation to him (it was our 1st date), he bought me a shot, i said good luck man, she's all yours. said bye to him and not her, and she got so mad at that lol.

In my youth I've had awkward dates. no need to explain. The typical young guy date where no one is talking and there's no plan.

---

pojr posted...

In my youth I've had awkward dates. no need to explain. The typical young guy date where no one is talking and there's no plan.

What kind of plans would later come to be?

---