Most awkward date you've had?

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KingUranus

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#51  Edited By KingUranus

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Enemybird

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#52  Edited By Enemybird

@TheCerealKillz said:

Blind date. she asked me sexual questions the entire time. I left.

you did what?

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joshmightbe

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#53  Edited By joshmightbe

That time my then girl friend's dad tried to have me arrested and even the cop said the whole thing was stupid

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krilling

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#54  Edited By krilling

Never had something like that.

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rogue_mar1e

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#55  Edited By rogue_mar1e

Don't ... remind me ... /shot

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X35

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#56  Edited By X35

too many... like once there was this guy who thought he was a vampire. like seriously. what's worse was i thought it was "quirky" instead of "insane".

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ssejllenrad

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#57  Edited By ssejllenrad

Don't know if awesome or awkward but on the first date with my non-geeky girlfriend (now fiance), she corrected me with all my Star Wars "fun facts" and she turned out to be right on about 90% of them corrections. I was supposed to be beauty and the geek! Not beautiful geek and geek!

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buttersdaman000

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#58  Edited By buttersdaman000

Met a girl at a party, hooked it up. Took the girl out the next day, turns out she was fat and ugly.

I hate alcohol

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sesquipedalophobe

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@_Black: That's pretty neat, actually.

@buttersdaman000: Stay drunk an entire week the next time this happens. Thank me later.

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Delphic

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#60  Edited By Delphic

I've had a couple of awkward ones. Went out with on girl that my parents sort of pushed me into, and she was a really hardcore fire and brimstone christian girl, so when she said she wanted to go see Ghost Rider for our first date I was honestly caught off guard.

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Enemybird

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#61  Edited By Enemybird

Whenever the girl isnt DTF its awkward for me... lol jk

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redleigh86

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#62  Edited By redleigh86

My most awkward date would easily be the date I never even knew I was on... I felt bad afterwards, but I genuinely had no idea.

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X35

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#63  Edited By X35

^

we've all been there. Really awk.

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Raiiyn

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#64  Edited By Raiiyn

I think the most awkward date Ive ever had would be the one where my date's mother (my date was 23) drove myself, my date and my date's little sister and brother to the amusement park...in her minivan... The car ride consisted mostly of my date's mother probing me as Italian mother's are want to do... ie: do you cook? do you go to church? how many children do you want?

This was our first date. Needless to say it was also the last.

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Hot_Karl

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#65  Edited By Hot_Karl

My first few were all pretty awkward. Never spent alone time with a girl my age at that point (I was barely 18?) so mostly just me struggling to think of topics to talk about, apologizing for being awkward, etc. No real insanely awkward dates that ended poorly though.

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Rogan2112

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#66  Edited By Rogan2112

My very first date EVER was SUPPOSED to be with this girl I like and several friends of mine. My friends wanted to see the movie Platoon when it first came out, so I invited her along figuring, y'know, ease her into things. This way it would be her coming with me to a movie with a group of people than the akwardness of a "first date". Well, NONE of my friends showed up, so we're stuck watching the (very very GOOD but DEPRESSING and sort of horrific) movie. with just the two of us. We had a few more dates, but how that date went pretty much set the tone for how the "relationship" would go. Akward is not even the world lol.

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jeanlucpicard

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#67  Edited By jeanlucpicard

well I wouldn't say everyone...

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vance_astro

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#68  Edited By vance_astro  Moderator

Took a chick to McDonald's,got her a cheesburger,she was ungrateful...

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vance_astro

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#69  Edited By vance_astro  Moderator
@Deranged Midget said:
She gave me a kiss at the end of the night which made up for it and we started seeing each other for about 2 weeks, but then she cheated on me with my best friend from grade school...  Since then, I have basically stopped caring.
Damn...
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_Black

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#70  Edited By _Black

@Vance Astro said:

Took a chick to McDonald's,got her a cheesburger,she was ungrateful...

Hahaha. How dare she.

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Deranged Midget

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#71  Edited By Deranged Midget

@Vance Astro said:

@Deranged Midget said:
She gave me a kiss at the end of the night which made up for it and we started seeing each other for about 2 weeks, but then she cheated on me with my best friend from grade school... Since then, I have basically stopped caring.
Damn...

Yeah... I'm not exactly the most open person when it comes to women anymore.

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Raiiyn

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#72  Edited By Raiiyn

@lykopis:

his mom definitely sounded like a keeper... monster-in-law much? ;P

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Phylos

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#73  Edited By Phylos

hmm, one of the stories that come to mind is when i met up with this guy at the movies. we were going to watch The Hangover 2 i believe. as we were sitting waiting for the movie to start, i lean in towards his face and tell him, "can we just watch movie? no kissing or touching.." his face was priceless, im guessing he thought i was leaning in for something else. after the movie he didnt really say anything, which made it awkward, so i just went home haha.

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The_Peter_Cosmic

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#74  Edited By The_Peter_Cosmic

Not a good date movie, but she really wanted to see it... We went to see The Boy in the Striped Pajamas and, well, it was a holocaust movie and let's just say it didn't end well for the child protagonists. She was horribly distraught like I've never seen a person, just wailing and sobbing violently. The problem was we went to see it before we went to dinner and she still wanted to go. All the way through dinner she never regained her composure and everyone in the place was shooting the most awful glares at me like I had done something truly awful to this poor girl.

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sesquipedalophobe

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I recently went out on a date with a girl I met through a friend. We sat, we talked about life in general, we laughed. For some reason we got on to the discussion of insurance and retirement. She asked if I could easily retire and I told her "oh, I have a nice package." I meant a retirement package. She knew what I meant, but laughed anyway. For the rest of the night I couldn't look her in the eye.

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TrueIlluminatus

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#76  Edited By TrueIlluminatus

Took a girl to see The Hangover: Part II. She laughed all the way through, while I sat there, awkwardly pretending to be genuinely interested and laughing, when I was really bored to tears the entire time. After that, we went to the Starbucks nearby, where we ran into an ex of mine that this girl used to be best friends with at one point in time. Then, her dad came and picked her up, and I ended up walking to a friend's place and getting drunk. The Hanogver: Part II was so bad that I literally needed alcohol to wash it away. 

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nickthedevil

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#77  Edited By nickthedevil

Halloween night, me and a girl i had struck up a convo and asked on a date were walking through a neighborhood, just talking. And all of a sudden a big varsity wrestler pulls up out of a white SUV, and i'm thinking: "whats this about?" he gives me a left hook before i can even process what the hell is going on, and after i hit tthe floor he kicks me when i'm down, and as i'm getting up he runs back into his car with his friends and drives off. turns out he was her steroid pumping boyfriend. So yea, in the middle of a residential area, kids and their mothers are looking a me... How embarrassed i was...

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VictorGrey

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#78  Edited By VictorGrey

@sesquipedalophobe said:

I recently went out on a date with a girl I met through a friend. We sat, we talked about life in general, we laughed. For some reason we got on to the discussion of insurance and retirement. She asked if I could easily retire and I told her "oh, I have a nice package." I meant a retirement package. She knew what I meant, but laughed anyway. For the rest of the night I couldn't look her in the eye.

ROFL

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texasdeathmatch

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#79  Edited By texasdeathmatch

My last ex and I were on our second date at some sushi restaurant. She got way too drunk off of saki shots, and when I tried to help her get out of her seat, she fell, pulling my pants down with her. So basically stood in a little Japanese restaurant with my pants down and my date on the floor next to me.

Cut to 20 min later she's puking in my bedroom trashcan and calling her dad on her cell. And I still wonder why we never worked out...

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gravitypress

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#80  Edited By gravitypress

I went on a first date once where the girl vomited around 10 times due to food poisoning. She really wanted to go and not disappoint me she said. She also had this dark purple lipstick all over her teeth. To top it all off she soiled herself while throwing up. We were in a different city on our date so I couldn't flee. Needless to say I wasn't calling her back but she kept coming over to my house till I gave her another shot. Long story short we are now married. (True story)

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TheCheeseStabber

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#81  Edited By TheCheeseStabber

Met a beautiful girl I had a lot in common with, so i offered to see a movie with her, and she excepted. So i arrived Her house and we were gonna go and see the movie. Her mom drives us even though I thought we'd be walking but i figure what the heck a free rides a ride. Well her mom makes me sit in the back seat with her daughter in the front till we get there. We arrive at the theater and we came to see a scary film, i dont remember what I think it was Paranormal Activity 2 or something. But she decides that because Due Date is playing she wants to see that, I'm like ok Fine what ever. So then she invites her mom to watch it with us. Her mom decides to sit in between us during the entire film in which the girl kept talking to her mom and didn't say a word to me. Then after she still ignores me and I'm driven back home with the girl in the passenger seat and me in the back. She asked if we could d it again some time, and I said maybe and walked inside. That was a very awkward date.

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jeanroygrant

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#82  Edited By jeanroygrant

@goldenshot80 said:

I am
No Caption Provided

FOREVER ALONE :'(

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sesquipedalophobe

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About three years ago some girl asked for a cigarette and a light while I was on break. I was about to go back inside when she grabbed my arm and handed me her phone number. Hesitant, I called her later and we eventually planned a movie date. We saw Youth in Revolt and she wouldn't keep quiet throughout the film, saying things like "that's so true!" and "that right there is funny, you know it?" The couple in front of us started a shouting contest with her, so she told them I knew martial arts (I don't). I apologized before we left.

After it was all over I thought we would go our separate ways, but she wanted to go eat some Arby's (I hate it). She picked at her food, disappointed by the quality of it. It was essentially a crap sandwich that tasted like all the other sandwiches they make, so I ignored it. She talked about selling drugs to old people till she was nineteen. She still used Myspace. Her friends were getting shot. She brought everything up on a first date you might tell someone after years of knowing them. I told her I was boring and lived a dull life, downplaying everything about me to depress her enough to cut the rest of the date short, but as it turned out I was the kind of guy she was looking for on accident, whatever that means. She made the most annoying sound with her ear.

On the way to her apartment complex a car stopped by us and her brother jumps out, reaches into his ass and pulls a bag out for her to hold till he can drop off his kids. I got her to the door and she used the same crappy hand to pull me in for a kiss. I scrubbed my face several times that night. I can't believe I agreed to a second date.

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Cozy_Da_Djed_Eye

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#84  Edited By Cozy_Da_Djed_Eye

When I was 13 I was dating this girl named Kanella from Texas but a cousin of mine wanted me to go out on a date with this other girl named Yasmine. He told me that he made a bet with Yasmine cus she didn't think I'd go out with her. He said the bet was for 20$ and he really needed the money. He promised me he'd buy me a 40 if I helped him win the bet.

The date was awkward cus I felt guilty the whole time. Couldn't even think straight or talk right. Yasmine thought I was nervous because I liked her.

After our date my cousin told me he never made a bet with her he just wanted to see me get some poon that night. Man I was so mad. I told Yasmine I had a girl and from then on all the Mexican girls called me "2-Timer-Person" I felt bad.