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Certified Legendary Thread Awkward Flirting Stories
- Thread starter CakeEater
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- Aug 7, 2008
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Nomination for GD TOTY 2011 thus far 
Smoooothy
SACK THE LOT OF THEM!
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subbed!
absolutely brilliant
i posted mine on the fail thread from memory
19 year old, having a house party for my 16 year old brother, girl comes up to me and after chatting for a while and wants to know if she can borrow a jacket, as it's cold
so i go off to my room, she follows, shuts the door and gets the jacket. then she says these words that have haunted me to this day
"you know, if i really like a guy, i'll swallow"
i grin, and leave my room, and grab another beer
opportunity for 16 year old BJ, gone forever
* (i did hook up with her later than night, but no action at all
)
You weren't wrong, that is classic
Some great stories in this thread so far, keep them coming!
this bloke legit sounds out of jersey shore
- Jun 23, 2008
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The classic video version of my earlier post :
[YOUTUBE]TmMna1EwZ1E[/YOUTUBE]
Genuinely lol'd at this. You can just picture him walking away from the door really pleased with himself at how "smart" as he was as well.
Anyway, I may as well drag out an old story of my own. I've mentioned it before in a "Moments of Epic Fail" thread last year, so longer-term GDers might recognise it, but it's kind of fitting for this thread too:
Going back a few years now to my first year at uni, I notice a girl in one of my classes who I think is quite attractive. I'm too shy and awkward to approach her, and she's always got a couple of friends around her (which could compound the umcomfortableness of getting shut down if I tried to chat her up), so I just pine from a distance. Anyway, fast forward a few weeks into the semester, and this girl has tracked me down on MySpace (back in the days when it was still popular), and sends me a message on there saying that she'd really like to meet me, and that she would have just came up and spoken to me, but thought I'd just brush her off if she approached, because she's kind of shy and awkward, and I appear to be pretty cool and stuff (exactly what I was thinking about her). Obviously I'm estatic about this turn of events, and we get along famously during classes over the next couple of weeks.
Eventually, we hang out a bit away from uni, and one day she comes over to my place for lunch. We're lying on my bed talking, and out of the blue she turns to me and says "You know, Vaselene is quite versatile. You can use it for lots of different things", totally unrelated to anything we'd been talking about previously. Me, totally missing the point and thinking what she said was very random, ends up replying with "Um, yea". Anyway, the day goes on with us just talking and she eventually leaves to go home, with nothing having happened between us but conversation. Honestly, I just entirely missed the point of the Vaseline thing at the time she said it (in the context of the conversation we were having, it was one of the most random comments I've heard in my time), but it struck me right in the face once I thought about it after she'd left, and it added further to the "Why didn't you make a move, you soft bastard?!" self-beating I dished out to myself anyway.
A few days later, in conversation with her, I make it clear to her that I like her as more than a friend, and in turn would like to be more than just friends, to which she explained to me that despite her strong physical attraction to me (which is what prompted her to track me down via the Internet in the first place) and recognition of the fact that we got on so well (as we had similar tastes in music and movies, and shared similar ideas about the world and sense of humour, which is really all you need as an 18-year-old), my lack of initiative in terms of initiating something physical between us has cost me, and therefore, no dice.
That was years ago, and I've obviously learnt from it since, but geez, such strong, strong fail
:[YOUTUBE]TmMna1EwZ1E[/YOUTUBE]
Genuinely lol'd at this. You can just picture him walking away from the door really pleased with himself at how "smart" as he was as well.
Anyway, I may as well drag out an old story of my own. I've mentioned it before in a "Moments of Epic Fail" thread last year, so longer-term GDers might recognise it, but it's kind of fitting for this thread too:
Going back a few years now to my first year at uni, I notice a girl in one of my classes who I think is quite attractive. I'm too shy and awkward to approach her, and she's always got a couple of friends around her (which could compound the umcomfortableness of getting shut down if I tried to chat her up), so I just pine from a distance. Anyway, fast forward a few weeks into the semester, and this girl has tracked me down on MySpace (back in the days when it was still popular), and sends me a message on there saying that she'd really like to meet me, and that she would have just came up and spoken to me, but thought I'd just brush her off if she approached, because she's kind of shy and awkward, and I appear to be pretty cool and stuff (exactly what I was thinking about her). Obviously I'm estatic about this turn of events, and we get along famously during classes over the next couple of weeks.
Eventually, we hang out a bit away from uni, and one day she comes over to my place for lunch. We're lying on my bed talking, and out of the blue she turns to me and says "You know, Vaselene is quite versatile. You can use it for lots of different things", totally unrelated to anything we'd been talking about previously. Me, totally missing the point and thinking what she said was very random, ends up replying with "Um, yea". Anyway, the day goes on with us just talking and she eventually leaves to go home, with nothing having happened between us but conversation. Honestly, I just entirely missed the point of the Vaseline thing at the time she said it (in the context of the conversation we were having, it was one of the most random comments I've heard in my time), but it struck me right in the face once I thought about it after she'd left, and it added further to the "Why didn't you make a move, you soft bastard?!" self-beating I dished out to myself anyway.
A few days later, in conversation with her, I make it clear to her that I like her as more than a friend, and in turn would like to be more than just friends, to which she explained to me that despite her strong physical attraction to me (which is what prompted her to track me down via the Internet in the first place) and recognition of the fact that we got on so well (as we had similar tastes in music and movies, and shared similar ideas about the world and sense of humour, which is really all you need as an 18-year-old), my lack of initiative in terms of initiating something physical between us has cost me, and therefore, no dice.
That was years ago, and I've obviously learnt from it since, but geez, such strong, strong fail
My entire life is made up of flirting awkwardness mainly because I like chasing and it's what I'm used to. When a girl comes on to me I freak out.
One of the worst is when I was 18 and I went back to this girls place who I'd had a crush on for years and it turns out she felt the same. So I was yawning a bit because it was late and we were joking that I was "too tired." Everything going smoothly and she says maybe we should get some sleep so we can go at it properly in the morning (as she's riding me wearing nothing but a pair of jeans, clearly just trying to tease the shit out of me). I say "Actually yeah I'm super tired, maybe we could go harder in the morning, I'm a bit out of it at the moment!" Then she started crying...
Earliest one was at one of those school discos everyone used to have where this girl was dirty dancing with me and I was all "holy shit! I'm 14 and what is this?" And getting pretty excited. So then she asks me outside for fresh air and I follow (having never kissed a girl at this age) and we're flirting and shit and I'm on absolute edge about macking the shit out of her. Then she leans in close and puts her hand on my thigh and grabs my phone through my pants and says "Give me your phone" and batters her eyelids. I'm too worked up about this girl being cm's from my raging boner to understand she wants to exchange numbers and I stand up and say; "Girls shouldn't just play with a guys feelings to get what they want, if you want a phone use the payphone by the school office" and storm off. Then she started crying...
And from the Awkward moments thread:
Hooking up with some chick when having the feeling of being watched. Turning around to see her (drunk) boyfriend standing about 30 cm's from my face with a big grin on his face winking at me and he slaps me on the arse. There was a very awkward silence for a loooong time.
...then she started crying.
One of the worst is when I was 18 and I went back to this girls place who I'd had a crush on for years and it turns out she felt the same. So I was yawning a bit because it was late and we were joking that I was "too tired." Everything going smoothly and she says maybe we should get some sleep so we can go at it properly in the morning (as she's riding me wearing nothing but a pair of jeans, clearly just trying to tease the shit out of me). I say "Actually yeah I'm super tired, maybe we could go harder in the morning, I'm a bit out of it at the moment!" Then she started crying...
Earliest one was at one of those school discos everyone used to have where this girl was dirty dancing with me and I was all "holy shit! I'm 14 and what is this?" And getting pretty excited. So then she asks me outside for fresh air and I follow (having never kissed a girl at this age) and we're flirting and shit and I'm on absolute edge about macking the shit out of her. Then she leans in close and puts her hand on my thigh and grabs my phone through my pants and says "Give me your phone" and batters her eyelids. I'm too worked up about this girl being cm's from my raging boner to understand she wants to exchange numbers and I stand up and say; "Girls shouldn't just play with a guys feelings to get what they want, if you want a phone use the payphone by the school office" and storm off. Then she started crying...
And from the Awkward moments thread:
Hooking up with some chick when having the feeling of being watched. Turning around to see her (drunk) boyfriend standing about 30 cm's from my face with a big grin on his face winking at me and he slaps me on the arse. There was a very awkward silence for a loooong time.
...then she started crying.
Hahahaha! Clearly some of you guys have autistic friends, or at least they may as well be. Unbelievable.
Brilliant.
d0gs
Club Legend
^^ Agreed. The most ultimate of burnings, at such a young age!! hahaha
Thread of the year and now here is my meaningless contributions, centering on my own misfortune back in high school.
First one, during a PE class me and some mates were sitting down waiting for others to finish up on the court. While waiting we were chatting up with the group of girls next to us. Just harmless talk going back and forth, subject of dating comes up.... stuffing around i was jokingly hamming it up and saying "how bout you and me" before i got cut off by the PE teacher who didn't like what was going on. Cuts me off and throws in the curve ball that i didn't stand a chance with her, and another jab at me. So i was pwned by the teacher.
Second instance was where i didn't take someone seriously in that she really was keen on hooking up with me. I was the quiet and reserved guy, who hung out one of the "cool cliques" in our year level, one of the girls in the group developed a strong liking towards me over time. She had dated a guy that i was mates with, i thought she was ace as a friend and would totally go "there" if i didn't think i was going to be throwing my mate's friendship under a bus.
It got to the point where she asked me out in front of the whole class, i did my best John McEnroe impersonation "you cannot be serious" and ran out of there, instantly knowing that my reaction to her was in front of everyone, and doubly as much later on when the person i didn't want to get in the shits with... basically said he would have given me the green light.
First one, during a PE class me and some mates were sitting down waiting for others to finish up on the court. While waiting we were chatting up with the group of girls next to us. Just harmless talk going back and forth, subject of dating comes up.... stuffing around i was jokingly hamming it up and saying "how bout you and me" before i got cut off by the PE teacher who didn't like what was going on. Cuts me off and throws in the curve ball that i didn't stand a chance with her, and another jab at me. So i was pwned by the teacher.
Second instance was where i didn't take someone seriously in that she really was keen on hooking up with me. I was the quiet and reserved guy, who hung out one of the "cool cliques" in our year level, one of the girls in the group developed a strong liking towards me over time. She had dated a guy that i was mates with, i thought she was ace as a friend and would totally go "there" if i didn't think i was going to be throwing my mate's friendship under a bus.
It got to the point where she asked me out in front of the whole class, i did my best John McEnroe impersonation "you cannot be serious" and ran out of there, instantly knowing that my reaction to her was in front of everyone
, and doubly as much later on when the person i didn't want to get in the shits with... basically said he would have given me the green light.
bresker
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- Sep 21, 2005
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There was this girl at uni really keen on me. I was pretty shy back then so I didn't speak to her for a long time - we just used to make cow eyes at each other in the library. Then she left a flower on my study desk (awww).
Finally because I didn't approach her she came up to me and said 'Hi I'm Rachel, we really should stop staring at each other and just talk.'
So I went and had lunch with her and we chatted a bit. But I'm not used to being chased by women (before or since, much) and I'm a terrible flirt. So I decided in my stupid mind that she was weird and 'too intense' because she kept going after me.
We met up around uni a few times after that. I have to tell you, she was pretty hot. Tall and slender. Massive eyes which I found a bit spooky but in retrospect they were attractive, really. I just decided in my low-self-esteemish mind that her large eyes made her a serial murderer or something for chasing me.
Anyway, I'm standing outside the lecture hall with her one day, about to go in for my Ancient History tutorial (yawn).
She says 'Forget about the lecture. Let's go and do something more interesting!' and looks at me with her big eyes.
Reader, I went into the lecture. And sometime after I told her best friend that she was 'too intense' and she stopped chasing after me. Last time I saw her, she started french kissing another bloke at a gig I was at, and she made sure I saw it.
Free sex at age 19
I had balls like spacehoppers!
TOTY BTW 6 flirts
Finally because I didn't approach her she came up to me and said 'Hi I'm Rachel, we really should stop staring at each other and just talk.'
So I went and had lunch with her and we chatted a bit. But I'm not used to being chased by women (before or since, much) and I'm a terrible flirt. So I decided in my stupid mind that she was weird and 'too intense' because she kept going after me.
We met up around uni a few times after that. I have to tell you, she was pretty hot. Tall and slender. Massive eyes which I found a bit spooky but in retrospect they were attractive, really. I just decided in my low-self-esteemish mind that her large eyes made her a serial murderer or something for chasing me.
Anyway, I'm standing outside the lecture hall with her one day, about to go in for my Ancient History tutorial (yawn).
She says 'Forget about the lecture. Let's go and do something more interesting!' and looks at me with her big eyes.
Reader, I went into the lecture. And sometime after I told her best friend that she was 'too intense' and she stopped chasing after me. Last time I saw her, she started french kissing another bloke at a gig I was at, and she made sure I saw it.
Free sex at age 19
TOTY BTW 6 flirts
wce_all_da_way
Norm Smith Medallist
LOL
People are.
Had a mate go outside the club with a girl and she said "oh gee it's so cold" to which he duly replied "well you should have brought a ****ing jacket" whilst putting his on. He didn't realise that he had a shot. She of course then excused herself, went back inside the club and got with another guy instead in front of him. Just terrible.
Plugger35
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Man what an idiot, how was he going to play his XBOX without batteries?
When I was 16 I went on a double date to the movies. It was my second date with this chick and we had only kissed. I buy some popcorn, jaffas and drinks. I am looking forward to getting my fingers wet and I already had a boner before we got in. For some reason back then fingering a girl was massive and all your mates would have laughs about smelling your hand etc. We sit in the back row because that was the best place to get some action without being caught and perved on. Also the mad cats sit at the back of the room/cinema.
So, for some reason its hot in the cinema and I start to sweat a bit. I was also excited about the eminent finger banging that would take place. So everything is going smooth, I'm eating my jaffas, my mate is kissing his chick and everything is peaches. I couldn't give a **** about the movie btw. So I start kissing my girl and feeling her t***ies, then slowly go the hand on crotch to wait for her reaction. She takes my hand and pushes it up against her cooch even harder, I tried to throw a googly and slip my hand behind her pants so I could touch it proper. The jeans were too tight and she pushed my hand away when I tried that, so I only got pants on pussy feeling. I was content with that and went back to kissing and touching.
So, the movie ends and we all start to walk out. I was talking shit with my mate and then when we get outside I look at my girl and see she has red jaffa stains all over her - it was like a crime scene with my hand prints all over her. Face, top and crotch where I was rubbing so hard a genie could have come out. I shit my pants and tell her to look in the mirror, she sees the horror and runs to the bathroom with my mates girl. I can't help but laughing and thinking I've ****ed this up real good. Anyway she manages to wash most the stains off and refuses to talk to me the rest of the day. That pretty much ruined what we had and we broke up.
CakeEater
Brownlow Medallist
- Thread starter
- #69
Given that I started this thread, I suppose I should tell one of my own stories.
Went out to a pub and got severly smashed (this girl i knew was working behind the bar and was giving me cocktails all night).
Anyways got a text from my mates saying that I should meet them in a club so I walked there and caught up with them.
Inside this club i saw this bartender I recognised and had a huge crush on.
She was wearing a nurses outfit and in my drunken haze and in front of all my mates I said to her Are you a chicken, because you look like finger licking chicken".
She just looked at me like WTF and I've copped it from my mates ever since then
Needless to say I wasnt succesful at all in picking her up either
Went out to a pub and got severly smashed (this girl i knew was working behind the bar and was giving me cocktails all night).
Anyways got a text from my mates saying that I should meet them in a club so I walked there and caught up with them.
Inside this club i saw this bartender I recognised and had a huge crush on.
She was wearing a nurses outfit and in my drunken haze and in front of all my mates I said to her Are you a chicken, because you look like finger licking chicken".
She just looked at me like WTF and I've copped it from my mates ever since then
Needless to say I wasnt succesful at all in picking her up either
Ed_Gein
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oh shit CakeEater, that attempt at a pickup line is ****ing hillarious. pissing myself.
Bateanator
Senior List
Been umming as to whether I should post this, but i think the time has come to exorcise my demons and let it out...it is...pretty horrific.
Around 18 months ago I had a free house as the rest of the family was down at our beach-house. As you do, I invited a number of individuals around to our premises, one of which being a girl which i was fairly (see very) keen on. Anyway the night’s going on in a relatively standard manner, when this girl and i strike up a bit of talk, she eventually asks for a drink, which I promptly obtained for her. Still being on her P’s, she pretty much can’t drink and drive on the same night, meaning of course, that she would have to stay the night- not that this resonated with me at the time however. Now this clearly isn’t so bad, but it gets much, much worse...
Later in the night, when by now she has consumed way too much alcohol to even be contemplating driving anywhere, she comes and sits on the couch next to me. We proceed to talk and watch a bit of late night television for the next hour or so. By now, it’s just me and her and a mate of mine left in the room, then, suddenly, completely out of the blue, she proceeds to take off her bra, complaining that it’s too uncomfortable, and throwing the undergarment on the floor, before resolutely staring at me eye-to-eye. I just sit there and say something along the lines of “yeah, I’d hate to wear a bra haha”, thinking that there’s no way she’d want to do anything in-front of my mate- she wasn’t that kind of girl....unbelievable.
Amazingly, this wasn’t the tip of the iceberg. After I don’t twig on the bra-removal routine, she then proceeds to say that she can’t go to sleep on this couch, so she’s going to my bedroom to use my bed, thinking I’m the perfect gentleman, I say yeah sure go ahead, I don’t mind a bit of chivalry. She walks off to my bed, while I lie on the couch and fall asleep.
Seeing her the next morning she just looks at me very strangely as though I’ve just killed her cat or something, before getting in her car and getting the hell out of there.
The absurd thing is that it didn’t actually register with me what had happened until at least a week later, on New Year’s Eve no less. To this day I still don’t quite understand what went through my head that night- I’m by no means clueless and I’m not exactly a total failure with girls either, but this was just mind-boggling. We still see each other around uni occasionally and I think it’s fair to say she recognises me as a total head-case.
I have been relatively successful in deleting this night from my memory until I saw this thread.
Around 18 months ago I had a free house as the rest of the family was down at our beach-house. As you do, I invited a number of individuals around to our premises, one of which being a girl which i was fairly (see very) keen on. Anyway the night’s going on in a relatively standard manner, when this girl and i strike up a bit of talk, she eventually asks for a drink, which I promptly obtained for her. Still being on her P’s, she pretty much can’t drink and drive on the same night, meaning of course, that she would have to stay the night- not that this resonated with me at the time however. Now this clearly isn’t so bad, but it gets much, much worse...
Later in the night, when by now she has consumed way too much alcohol to even be contemplating driving anywhere, she comes and sits on the couch next to me. We proceed to talk and watch a bit of late night television for the next hour or so. By now, it’s just me and her and a mate of mine left in the room, then, suddenly, completely out of the blue, she proceeds to take off her bra, complaining that it’s too uncomfortable, and throwing the undergarment on the floor, before resolutely staring at me eye-to-eye. I just sit there and say something along the lines of “yeah, I’d hate to wear a bra haha”, thinking that there’s no way she’d want to do anything in-front of my mate- she wasn’t that kind of girl....unbelievable.
Amazingly, this wasn’t the tip of the iceberg. After I don’t twig on the bra-removal routine, she then proceeds to say that she can’t go to sleep on this couch, so she’s going to my bedroom to use my bed, thinking I’m the perfect gentleman, I say yeah sure go ahead, I don’t mind a bit of chivalry. She walks off to my bed, while I lie on the couch and fall asleep.
Seeing her the next morning she just looks at me very strangely as though I’ve just killed her cat or something, before getting in her car and getting the hell out of there.
The absurd thing is that it didn’t actually register with me what had happened until at least a week later, on New Year’s Eve no less. To this day I still don’t quite understand what went through my head that night- I’m by no means clueless and I’m not exactly a total failure with girls either, but this was just mind-boggling. We still see each other around uni occasionally and I think it’s fair to say she recognises me as a total head-case.
I have been relatively successful in deleting this night from my memory until I saw this thread.
- Aug 7, 2008
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it's the chivalry that did it.
trying to do what you think at the time is the "right thing" generally isn't, in their eys, necessarily so.
Haha, Gold Bateanator. My story isin't that obvious! or that good to be honest.
When I was about 16, girl from school had a house party as parents were away. There were alot of people there and everyone was pretty drunk.
I went upstairs to see a group (4 or 5) of people in the Room where this girl was, she was pretty sick (ie about to throw up). After abit of chat amongst the group she asks everyone too leave but asks for ME to stay.
I pause for a second and replied "I was about to get a drink, You (to her friend) stay with her ok?" and walked off.
After walking downstairs, opening a drink, I continued to mingle with others. Didn't hit me till the next day.
I wasn't garanteed anything but this hot girl wanted just me to be in her room with her for the rest of the night. We were just friends and there had not been any previous flirting as such. What could have been?
When I was about 16, girl from school had a house party as parents were away. There were alot of people there and everyone was pretty drunk.
I went upstairs to see a group (4 or 5) of people in the Room where this girl was, she was pretty sick (ie about to throw up). After abit of chat amongst the group she asks everyone too leave but asks for ME to stay.
I pause for a second and replied "I was about to get a drink, You (to her friend) stay with her ok?" and walked off.
After walking downstairs, opening a drink, I continued to mingle with others. Didn't hit me till the next day.
I wasn't garanteed anything but this hot girl wanted just me to be in her room with her for the rest of the night. We were just friends and there had not been any previous flirting as such. What could have been?
The Goon
Norm Smith Medallist
Batenator's reminded my of another one I've had from a while back when I was ******ed with girls and never been laid, but they seemed to love it. I must have been hanging out in **** central, because god knows why any of them went for me. Anyway I'm at a party and flirting with this chick who was pretty hot, but a bit of a shy one. I hadn't ever seen her around, but her friend said she knew me and thought I was a nice guy so I'm feeling pretty good about this (being "that guy" a girl likes from afar was new).
So I'm putting the moves on this nice girl and she's loving it. We hook up and she's a bit nervous, but let's me feel her up a bit and is really getting in to it. Anyway she pushes me off her after a while and says "meet me in 'Michael's' bedroom at 3" lunges in for a pretty intense mack and then runs off.
For the next 20 minutes I sat there with a fat grin on my face while everyone was heading to bed and psyching myself up for what was about to happen. Five minutes to 3 it struck me I had no ****ing idea who 'Michael' was or where his room was. So I start freaking out and running around the place peeking into rooms to see this girl. The rooms are mostly pitchblack so I have to walk in and prod the people on the bed to ask "hey are you that girl I was hooking up with earlier" (I'd forgotten her name). A few of the rooms I went in to clearly were "occupied" so at about 3:45 after wandering this house and going into the same rooms repeatedly, asking people who are still awake if they had seen her, etc I go back to the couch all dejected and fall asleep.
Later in the night I wake up to the girl's stifled scream and see her pointing straight at me and babbling random shit, before turning around to see the 26 year old older brother of the girl throwing the party, 'Michael' saunter out of his room and go make himself some cereal. She'd been screwing him all night thinking it was me.
Didn't lose my virginity for ages after this... Was depressing.
So I'm putting the moves on this nice girl and she's loving it. We hook up and she's a bit nervous, but let's me feel her up a bit and is really getting in to it. Anyway she pushes me off her after a while and says "meet me in 'Michael's' bedroom at 3" lunges in for a pretty intense mack and then runs off.
For the next 20 minutes I sat there with a fat grin on my face while everyone was heading to bed and psyching myself up for what was about to happen. Five minutes to 3 it struck me I had no ****ing idea who 'Michael' was or where his room was. So I start freaking out and running around the place peeking into rooms to see this girl. The rooms are mostly pitchblack so I have to walk in and prod the people on the bed to ask "hey are you that girl I was hooking up with earlier" (I'd forgotten her name). A few of the rooms I went in to clearly were "occupied" so at about 3:45 after wandering this house and going into the same rooms repeatedly, asking people who are still awake if they had seen her, etc I go back to the couch all dejected and fall asleep.
Later in the night I wake up to the girl's stifled scream and see her pointing straight at me and babbling random shit, before turning around to see the 26 year old older brother of the girl throwing the party, 'Michael' saunter out of his room and go make himself some cereal. She'd been screwing him all night thinking it was me.
Didn't lose my virginity for ages after this... Was depressing.
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