Certified Legendary Thread Awkward Flirting Stories

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First ever time at a nightclub when I lived in Townsville as an 18/19 year old and I am sitting awkwardly in a corner nursing a beer.

Really, really nice looking girl pretty much power-walks up to me with intent and almost shoves the person sitting a foot or two away to get in real close to me.

Absolutely s**t-scared with surprise, I pretty much just stare straight ahead at some people dancing.

I'm sure she is staring at the side of my head for something like a full minute.

She leans in and says over the music, "Aren't you going to say hi??!".

My brain somehow melts even more, so I just flash a super awkward grin at her and hold it for an uncomfortably long time, not knowing what to do.

She shakes her head, gets up and leaves.

I go home.






Best. Night. Ever.
 
ShanDog said:
First ever time at a nightclub when I lived in Townsville as an 18/19 year old and I am sitting awkwardly in a corner nursing a beer.

Really, really nice looking girl pretty much power-walks up to me with intent and almost shoves the person sitting a foot or two away to get in real close to me.

Absolutely s**t-scared with surprise, I pretty much just stare straight ahead at some people dancing.

I'm sure she is staring at the side of my head for something like a full minute.

She leans in and says over the music, "Aren't you going to say hi??!".

My brain somehow melts even more, so I just flash a super awkward grin at her and hold it for an uncomfortably long time, not knowing what to do.

She shakes her head, gets up and leaves.

I go home.






Best. Night. Ever.
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You're either incredibly unlucky, or incredibly lucky. I can't quite work out which yet.

You may have avoided being brutally murdered because of your shyness.

Either that, or you missed the best night of your life.

Either or.
 

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Sublime said:
You're either incredibly unlucky, or incredibly lucky. I can't quite work out which yet.

You may have avoided being brutally murdered because of your shyness.

Either that, or you missed the best night of your life.

Either or.
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Haha I reckon if I responded I would have sounded like that red-head guy on the Simpsons who's voice is always breaking.

Geez I copped some s**t from my mates after that one lol
 
DarkPhoenix said:
Unfortunately she's about as comfortable with balls up around her chin as Shane Watson is and flat out denies my request.
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DarkPhoenix, just reliving some great stories and this line actually had me in such hysterics that I had to excuse myself from my university lecture.
 
Gibbsy said:
We need more DarkPhoenix

You're too articulate to not contribute at least once more in this thread.
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I've gone the way of Nate :( Female friend.

I'll try and think of some oldies though.
 
No where near as funny as some in here, but a story of mine made for a horribly awkward situation (hope it makes sense).

So I had been friends with this chick for a while, 2-3 years, and every now and then we'd chat on facebook, or in person when our mutual friends bumped into each other on nights out. She's a definite 7, but loves footy and cricket, wife material s**t, which bumps her up to 8. Cute, slightly/not so shy, hottie that everyone couldn't believe she was still a virgin by her 18th bday (where one of her friends gave a speech indicating this to plenty of respectful lol's). So I feel we'd had a connection for awhile but nothing had ever come of it, no dates, no hook ups, nothing but hugs.

So to the main story, we were in one of those phases where we would chat every so often, btw shes 18 and I'm 19 at this point in time. So shes messages me latish (10:30pm) on a Sunday night after shes come back from a Sunday session. Im just chilling out watching some quality EPL. She's being flirty and invites me over to her house about 11pm. First thought that comes into mind is "* yes, finally gunna make it happen". I've wanted to participate in sexual acts with her for ages/ maybe lead to a relo situation. So I get to hers, shes a bit tipsy telling me to be quite as her parents and sisters are asleep. Not ideal, but you take your chances. Se we're chatting for a bit in her room, and genuinely as I'm about to pull the swifty and go in for the kiss to get things started she says "you've been here for 30mins and havent tried to kiss me, whats with that?" Great, awkwardness starts. She then states "Oh I didnt mean to make it awkward" I say, "you didnt" and go in for the kiss and things start happening like normal. You beauty.

Foreplay is foreplay and it's my turn to please her first. I could go into detail of some awkwardness here but it's no where near appropriate. So things are rollicking along, and she flings her self on top of me. She works her way done, belt first etc. First thing that pops into my mind is that I havent had a bat today so a bj wont last long so I'd rather have sex (young and silly not knowing my abilities as a male at this point in life). So with my coolness are say, "do you wanna have sex?". She looks at me and a smile turns to a droopy face in a split second.
Her: Im still a virgin
Me: Oh thats cool, I dont mind.
Her: * looks away from me kinda awkwardly*
Her: I was kinda saving it for someone else
Me: :$:confused:
Her: im sorry, I said I'd lose it to him. I really want to but I cant
Me: in my head *You're kidding me*

So here I am awkwardly as sitting with a raging boner with my pants half pulled off, with a hot virgin chick telling me she doesnt wanna have sex.
"ok" I think to my self "I can salvage the sitch"
Me: That's ok, we can forget about that.

She removes her self from being on top of me and starts getting slightly emotional and sorry saying "im sorry". I go in for another grab of her parts, she slaps my hand away, and then and there the moment of passion has completely ended. She's not giving any and shes totally off it now. Im cursing my self in my head "why couldn't I just let her continue to give me a BJ and not be greedy and go for the sex". We then lay in bed for the next 30mins awkwardly trying to make sense of the situation which was making it terribly worse.

To this day, I'm spewing I didnt get anything from this experience and my mates make me remember it often. I was greedy, wanted to take the virginity that was highly sort after it seems, but instead got the epic cold shoulder. We didn't speak for another 6 months...
 
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BluesMan said:
No where near as funny as some in here, but a story of mine made for a horribly awkward situation (hope it makes sense).

So I had been friends with this chick for a while, 2-3 years, and every now and then we'd chat on facebook, or in person when our mutual friends bumped into each other on nights out. She's a definite 7, but loves footy and cricket, wife material s**t, which bumps her up to 8. Cute, slightly/not so shy, hottie that everyone couldn't believe she was still a virgin by her 18th bday (where one of her friends gave a speech indicating this to plenty of respectful lol's). So I feel we'd had a connection for awhile but nothing had ever come of it, no dates, no hook ups, nothing but hugs.

So to the main story, we were in one of those phases where we would chat every so often, btw shes 18 and I'm 19 at this point in time. So shes messages me latish (10:30pm) on a Sunday night after shes come back from a Sunday session. Im just chilling out watching some quality EPL. She's being flirty and invites me over to her house about 11pm. First thought that comes into mind is "**** yes, finally gunna make it happen". I've wanted to participate in sexual acts with her for ages/ maybe lead to a relo situation. So I get to hers, shes a bit tipsy telling me to be quite as her parents and sisters are asleep. Not ideal, but you take your chances. Se we're chatting for a bit in her room, and genuinely as I'm about to pull the swifty and go in for the kiss to get things started she says "you've been here for 30mins and havent tried to kiss me, whats with that?" Great, awkwardness starts. She then states "Oh I didnt mean to make it awkward" I say, "you didnt" and go in for the kiss and things start happening like normal. You beauty.

Foreplay is foreplay and it's my turn to please her first. I could go into detail of some awkwardness here but it's no where near appropriate. So things are rollicking along, and she flings her self on top of me. She works her way done, belt first etc. First thing that pops into my mind is that I havent had a bat today so a bj wont last long so I'd rather have sex (young and silly not knowing my abilities as a male at this point in life). So with my coolness are say, "do you wanna have sex?". She looks at me and a smile turns to a droopy face in a split second.
Her: Im still a virgin
Me: Oh thats cool, I dont mind.
Her: * looks away from me kinda awkwardly*
Her: I was kinda saving it for someone else
Me: :$:confused:
Her: im sorry, I said I'd lose it to him. I really want to but I cant
Me: in my head *You're kidding me*

So here I am awkwardly as sitting with a raging boner with my pants half pulled off, with a hot virgin chick telling me she doesnt wanna have sex.
"ok" I think to my self "I can salvage the sitch"
Me: That's ok, we can forget about that.

She removes her self from being on top of me and starts getting slightly emotional and sorry saying "im sorry". I go in for another grab of her parts, she slaps my hand away, and then and there the moment of passion has completely ended. She's not giving any and shes totally off it now. Im cursing my self in my head "why couldn't I just let her continue to give me a BJ and not be greedy and go for the sex". We then lay in bed for the next 30mins awkwardly trying to make sense of the situation which was making it terribly worse.

To this day, I'm spewing I did get anything from this experience and my mates make me remember it often. I was greedy, wanted to take the virginity that was highly sort after it seems, but instead got the epic cold shoulder. We didn't speak for another 6 months...
Click to expand...

How long ago was this?
 
So who was the bloke she promised? Ever find out why?
 

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Thats how I would normally take it, but it literally says she promised someone in particular.

You'd hope its like a really good old boyfriend that moved interstate or something. Similar happened with me (not losing the Vs though), had a GF who moved away when I was younger and we got together and slapped genitals together later on to make up for the sex we never got to have.

Actually an awkward story in there as well possibly.

Pea Nut said:
I find it quite bizarre that it would be someone in particular rather than just waiting for marriage or waiting for "the one" ??
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A similar sort of thing happened to me a few years ago. I was at a small gathering with 10 or so people at a friends place who was housesitting. Everyone goes to bed, me and a female friend were the last two left awake. We'd been friends for a couple of years prior. One thing led to another, we hooked up, got her into the bedroom, was literally naked on top of her and she stopped me. Said she'd only had sex once and didn't want to be 'that kind of girl'. There's no way to come back from that.

Fast forward a couple of weeks and she becomes 'that kind of girl' ;)
 
Yeah I know 'of' the bloke she wanted to lose it to. Im pretty sure they would have by now but not sure. They were kinda seeing each other at the time.. I think. I actually don't really know.

I'm confident she would of done it by now. The reason I decided to write the story was because we saw each other out a week back. She said we should catch up more, but not sexually this time and it was awkward last time... yeah no s**t :$ She's a confusing one to read.
 
Dont know if its been brought up in the thread before, but for anyone who likes a good read on this sort of subject, a guy who called himself 'Storybro' wrote a green text epic on 4chan that became so popular he would almost break the site as he continued the story every few nights for a couple of hours. Ended up writing more than one, all (supposed) true accounts that happened to him. The first is about a sleepover party that gets very out of hand.

If you search for Storybro's Magically Lewd Sleepover, I'm sure you will find it.

Despite being 4chan text, each story is the length of a thesis lol. Very entertaining anyway.
 
BluesMan said:
Yeah I know 'of' the bloke she wanted to lose it to. Im pretty sure they would have by now but not sure. They were kinda seeing each other at the time.. I think. I actually don't really know.

I'm confident she would of done it by now. The reason I decided to write the story was because we saw each other out a week back. She said we should catch up more, but not sexually this time and it was awkward last time... yeah no s**t :$ She's a confusing one to read.
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Get her drunk, ask if it happened, if she says it did, nail her, if she says it didn't nail her.

Win-win for you.
 
Have a story from a friend who went on a tinder date.

He is recently single so has been smashing the app and basically swipes right all the time. Anyway got an Asian girls digits and he took her on a date to Hilary's boat harbour.

During the conversation, he realised that she was one of the poorest banterers in the land and always on her phone and that she looked nothing like the photos on tinder. He feigned that he needed to go to the toilet.

He proceeded to leave Hilary's and her there.

He decided not to be too rude and texted her this:

"Hey sorry I had to bail. I wasn't feeling too great and I couldn't make the toilet in time and I've ended up pooping all over my pants. I was too embarrassed so I have to leave. Sorry".

She wasn't too happy considering he was her ride too!
 
bok_party said:
Have a story from a friend who went on a tinder date.

He is recently single so has been smashing the app and basically swipes right all the time. Anyway got an Asian girls digits and he took her on a date to Hilary's boat harbour.

During the conversation, he realised that she was one of the poorest banterers in the land and always on her phone and that she looked nothing like the photos on tinder. He feigned that he needed to go to the toilet.

He proceeded to leave Hilary's and her there.

He decided not to be too rude and texted her this:

"Hey sorry I had to bail. I wasn't feeling too great and I couldn't make the toilet in time and I've ended up pooping all over my pants. I was too embarrassed so I have to leave. Sorry".

She wasn't too happy considering he was her ride too!
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That's not awkward, your mate just sounds like a complete dickhead.
 
bok_party said:
Have a story from a friend who went on a tinder date.

He is recently single so has been smashing the app and basically swipes right all the time. Anyway got an Asian girls digits and he took her on a date to Hilary's boat harbour.

During the conversation, he realised that she was one of the poorest banterers in the land and always on her phone and that she looked nothing like the photos on tinder. He feigned that he needed to go to the toilet.

He proceeded to leave Hilary's and her there.

He decided not to be too rude and texted her this:

"Hey sorry I had to bail. I wasn't feeling too great and I couldn't make the toilet in time and I've ended up pooping all over my pants. I was too embarrassed so I have to leave. Sorry".

She wasn't too happy considering he was her ride too!
Click to expand...
Lmaooo I did the same thing except it was in Bali and I at least finished the coffee then as we were leaving I jumped on my scooter and fanged it
 
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