Certified Legendary Thread Awkward Flirting Stories

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i once had a neighbour who was at the time in her early-mid 30s. one of those ladies who looked hot when she didnt smile. when she did it wasnt as pretty. so yeah. i was in my early 30s. one day it was announced that my presence was required at hers for dinner this coming sat night. so i said yeah sure cool. that was a week before the day. a few texts confirmed it. then the morn before i knocked on her door before work, she answered and opened door. conversation:

me: are we still on for tomorrow?
her: yes! are we still on?
me: yes
see you later blah blah

i was excited.

the night came, and i knocked on her door, she opened door. we had pre dinner drinks and sat on a sofa. i was a 2 seater. i sat perfectly perpendicular to the sofa back. she sat with legs folded up angling towards me. like this (without the shutterstock logo)

stock-photo-girl-sitting-on-the-sofa-hugging-his-arms-legs-71605792.jpg


music was playing in background. i think it was her mp3 mixtape.

dinner was ready, green curry chicken and rice. she apologised for its sogginess. i said it was fine and complimented it. i think we ate on the sofa. not sure. maybe on the sofa. anyway, after dinner we moved to the tv room, another sofa. this time it was a 3 seated. i sat on the right (if you are sitting on it), she middle/left. she idly flicked through channels on foxtel. tension in the air, nothing on. i said "try comedy channel". one of those political satires was on. colbert. and then stewart. it was getting late. i went to grab remote for some reason, she snatched it off the sofa. i giggled and leaned over. there was a bit of arm on arm action. i relented and sagged back. she pulled her shirt away from her ample bosoms and feigned putting remote down her shirt. i said "go on, do it i dare ya. ill go get it". she half smiled (chris judd like) and then said no you wouldnt. ego bruised.

stuff it. i leaned if and we shared a cuddle. she closed her eyes and i was weary. so we rested together. moments later, her eyes were still closed. i whispered "are you asleep?", she replied "just dozing", and i gently gave her a peck on her jawline. she giggled and said quietly "you're promiscuous". a moment after some awkward time and silence, she didnt really give any signs. i asked "what does promiscuous mean?". she opened and rolled her eyes and said she's going to get the dictionary. okayyyyyyy.........she returned with said dictionary and read out the meaning. i was still in the world of what the hell is going on here?

so i moved and we both took deep breathes. i go "i gotta go". she walked me to teh door. thanked her for tea and opened front door. i looked back and said sorry, then planted kiss on cheek. she put her hands on my face and kissed on on each cheek. back and forth as i closed door behind me. a hug. stopped and looked at each other. i left and walked home.

got home and thought wtf did u just do???? beat myself over it. watched team usa vs australia boomers basketball game pre-olympic warm up game i recorded earlier that day. kept thinking about opportunity missed. thought damn it, gonna bat one out. couldnt so depressed was i.

went to sleep and cried.
 
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DarkPhoenix said:
Honestly thought I was going to have a new AFS for you lot after last night, unfortunately it went spectacularly well for me.

#SubtleBrag
Click to expand...

End up in a public toilet/public gardens?
 
was at a pub a couple of weeks ago, cheap drinks so it was a fairly busy night

saw a *ing amazing bird who was genuinely a 8/9, and thought i may have a crack. now im not the best flirter at the best of times, and i'd have to have one of the rudest lids going around, but i was absolutely stevie wonder'd so i thought I'd have a crack

my mates and I were speaking in a group conversation to her, another girl she was with, and some random lady, presumably in her 50's or so

i wasnt completely engaged in the conversation as i was in a shitter state than digby morrell. i heard something about "shes turning 18 tomorrow" coming from the hot girl, here's how it transpired afterwards:

Me: No0ooo *ing way is she 18! are you serious?

Hot girl: yes she is, thats my ******* sister..... (was talking about the girl she was with). as you can tell, off to a bad start.

Me: ooooh * my bad! i thought you were talking about the ******* old lady!

Hot girl: thats my ******* mum......


Needless to say i evacuated the scene shortly afterwards and am still traumatised by the experience
 
Sammymoite said:
was at a pub a couple of weeks ago, cheap drinks so it was a fairly busy night

saw a ruddy amazing bird who was genuinely a 8/9, and thought i may have a crack. now im not the best flirter at the best of times, and i'd have to have one of the rudest lids going around, but i was absolutely stevie wonder'd so i thought I'd have a crack

my mates and I were speaking in a group conversation to her, another girl she was with, and some random lady, presumably in her 50's or so

i wasnt completely engaged in the conversation as i was in a shitter state than digby morrell. i heard something about "shes turning 18 tomorrow" coming from the hot girl, here's how it transpired afterwards:

Me: No0ooo ruddy way is she 18! are you serious?

Hot girl: yes she is, thats my ******* sister..... (was talking about the girl she was with). as you can tell, off to a bad start.

Me: ooooh **** my bad! i thought you were talking about the ******* old lady!

Hot girl: thats my ******* mum......


Needless to say i evacuated the scene shortly afterwards and am still traumatised by the experience
Click to expand...

Being stevie wondered is the best expression for being pissed I've ever heard. Funny story but * I'm glad you used that phrase, I'm going to be bringing that one out regularly.
 
Sammymoite said:
was at a pub a couple of weeks ago, cheap drinks so it was a fairly busy night

saw a ruddy amazing bird who was genuinely a 8/9, and thought i may have a crack. now im not the best flirter at the best of times, and i'd have to have one of the rudest lids going around, but i was absolutely stevie wonder'd so i thought I'd have a crack

my mates and I were speaking in a group conversation to her, another girl she was with, and some random lady, presumably in her 50's or so

i wasnt completely engaged in the conversation as i was in a shitter state than digby morrell. i heard something about "shes turning 18 tomorrow" coming from the hot girl, here's how it transpired afterwards:

Me: No0ooo ruddy way is she 18! are you serious?

Hot girl: yes she is, thats my ******* sister..... (was talking about the girl she was with). as you can tell, off to a bad start.

Me: ooooh **** my bad! i thought you were talking about the ******* old lady!

Hot girl: thats my ******* mum......


Needless to say i evacuated the scene shortly afterwards and am still traumatised by the experience
Click to expand...

Haha, you legend.

I was drunk as s**t one night, and so my brain doesn't have too much of a filter when that happens. It also doesn't pay attention to detail, such as the identification of the correct person.

Anyway, a few mates and I were talking to some girls. One of them says to a friend "I can't believe you're turning 33 next week". So I turn to the girl who I thought she was talking to (trying to be smooth, mind you) and said "You don't look that old. Maybe 28, 29?". Turns out she wasn't the girl in question, and also, she was 22.

I inadvertently told a 22 year old she looked 29. The awkwardness was palpable.

My mates were in tears. Meanwhile, Olay stocks most likely saw a significant increase that week, due to the amount of product she probably bought.
 
Alright ladies and gentlemen, sadly I have to post in here yet again.

So there's this girl I have a bit of a thing for. I mentioned her a few weeks ago in the "Bigfooty's Guide to Getting the Woman of Your Dreams" thread. Funny, smart, pretty damn attractive. Enjoys beer, wakeboarding and hitting the slopes. Seems interested in me. Well, seemed. Looks: 8.5. Personality: 9.5. A.K.A. girlfriend material.

So we're having a bit of a chat at lunch. She's going up to Mt. Buller for a couple of weeks, so we were talking about that. Another girl who works in the office comes up and we exchange pleasantries. "Oh, by the way, I saw you on Tinder. I swiped right for a laugh". "Haha, oh okay. I never use it anyway. It was only for a bit of a laugh". "Really? When I saw you come up before, it said that you were on about ten minutes prior". "F*ck me dead. Why would you say that?", I thought. "Oh, right..." The girl I'm keen on gives me a look similar to this:

o-EMMA-WATSON-50-SHADES-facebook.jpg


As if to say, "Really? Tinder?".

Alright, damage control mode. You aren't a sexual deviant. You don't agree with judging a girl solely on her looks. You joined simply for a bit of banter with the lads. (All true). Except now she thinks you're like the hoi polloi of Generation Y males; advocating a "hot or not" system of interaction, needing instant gratification through the means of receiving ego-boosting "matches", and willing to fornicate with anyone either remotely attractive or containing appealing orifices. (NB: I'm not claiming to be morally superior in general, just morally superior according to her idea of virtuosity).

So, I look back at her with a look reminiscent of this:

27359039-27359043-large.jpg


I then piss off for a couple of hours, half concentrating on work, half concentrating on how I'm going to Houdini this s**t, and escape with my dignity and self-respect in-tact.

We bump into each other later, and me being my notoriously smooth-as-s**t self, mumbled absolute nonsense for about thirty seconds. After I composed myself, I proceeded to say that "Tinder's s**t, that it degrades women by using them as sexual objects, and that my mates forced me to do it". I actually ranted on about sexual objectification for a couple of minutes (keeping in mind that the people on Tinder actually choose to be there, and in turn, be objectified based on physical appearance), because I thought that's what she wanted to hear. Pathetic, I know.

So, rather than laugh it off as simply a bit of banter between mates, I blamed the app for "being s**t", I went on an over-the-top try-hard leftist rant on the sexual objectification of women, which I only said in some futile effort to impress her, and finally I copped out big time by blaming my mates for "forcing me" to use the app, when in actual fact, it was an agreed upon activity between mates for the purposes of general banter.

I went from having an awesome girl keen on me, to being a clumsy moron with temporary social ineptitude (as you can tell, I experience social ineptitude quite frequently based on my stories on this thread). All this from being found on Tinder. Way to make a simple problem f*cking difficult.

Was not a good day in the life of Croweater. To make matters worse she leaves for the slopes for a couple of weeks, which means that I won't see her for a while. I'll text her during the week explaining everything, but I might have stuffed everything up.

Here's hoping she finds my idiosyncrasies endearing. :$
 
Last edited:
Croweater said:
Was not a good day in the life of Croweater. To make matters worse she leaves for the slopes for a couple of weeks, which means that I won't see her for a while. I'll text her during the week explaining everything, but I might have stuffed everything up.

Here's hoping she finds my idiosyncrasies endearing. :$
Click to expand...

Don't! You clearly have a way with words, so probably best to let it blow over and hope she's forgotten about it by the time she gets back. :p

Don't dig yourself into a deeper hole.
 

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At most a "hope you're having a great time skiing". She'll do the rest if there is anything left to salvage.
 
peternorth said:
i once had a neighbour who was at the time in her early-mid 30s. one of those ladies who looked hot when she didnt smile. when she did it wasnt as pretty. so yeah. i was in my early 30s. one day it was announced that my presence was required at hers for dinner this coming sat night. so i said yeah sure cool. that was a week before the day. a few texts confirmed it. then the morn before i knocked on her door before work, she answered and opened door. conversation:

me: are we still on for tomorrow?
her: yes! are we still on?
me: yes
see you later blah blah

i was excited.

the night came, and i knocked on her door, she opened door. we had pre dinner drinks and sat on a sofa. i was a 2 seater. i sat perfectly perpendicular to the sofa back. she sat with legs folded up angling towards me. like this (without the shutterstock logo)

stock-photo-girl-sitting-on-the-sofa-hugging-his-arms-legs-71605792.jpg


music was playing in background. i think it was her mp3 mixtape.

dinner was ready, green curry chicken and rice. she apologised for its sogginess. i said it was fine and complimented it. i think we ate on the sofa. not sure. maybe on the sofa. anyway, after dinner we moved to the tv room, another sofa. this time it was a 3 seated. i sat on the right (if you are sitting on it), she middle/left. she idly flicked through channels on foxtel. tension in the air, nothing on. i said "try comedy channel". one of those political satires was on. colbert. and then stewart. it was getting late. i went to grab remote for some reason, she snatched it off the sofa. i giggled and leaned over. there was a bit of arm on arm action. i relented and sagged back. she pulled her shirt away from her ample bosoms and feigned putting remote down her shirt. i said "go on, do it i dare ya. ill go get it". she half smiled (chris judd like) and then said no you wouldnt. ego bruised.

stuff it. i leaned if and we shared a cuddle. she closed her eyes and i was weary. so we rested together and i gently gave her a peck on her jawline. she giggled and said quietly "you're promiscuous". a moment after some awkward time and silence, she didnt really give any signs. so i moved and we both took deep breathes. i go "i gotta go". she walked me to teh door. thanked her for tea and opened front door. i looked back and said sorry, then planted kiss on cheek. she put her hands on my face and kissed on on each cheek. back and forth as i closed door behind me. a hug. stopped and looked at each other. i left and walked home.

got home and thought wtf did u just do???? beat myself over it. watched team usa vs australia boomers basketball game pre-olympic warm up game i recorded earlier that day. kept thinking about opportunity missed. thought damn it, gonna bat one out. couldnt so depressed was i.

went to sleep and cried.
Click to expand...
Youcannotbeserious.jpeg
 
Croweater said:
Alright ladies and gentlemen, sadly I have to post in here yet again.

So there's this girl I have a bit of a thing for. I mentioned her a few weeks ago in the "Bigfooty's Guide to Getting the Woman of Your Dreams" thread. Funny, smart, pretty damn attractive. Enjoys beer, wakeboarding and hitting the slopes. Seems interested in me. Well, seemed. Looks: 8.5. Personality: 9.5. A.K.A. girlfriend material.

So we're having a bit of a chat at lunch. She's going up to Mt. Buller for a couple of weeks, so we were talking about that. Another girl who works in the office comes up and we exchange pleasantries. "Oh, by the way, I saw you on Tinder. I swiped right for a laugh". "Haha, oh okay. I never use it anyway. It was only for a bit of a laugh". "Really? When I saw you come up before, it said that you were on about ten minutes prior". "F*ck me dead. Why would you say that?", I thought. "Oh, right..." The girl I'm keen on gives me a look similar to this:

o-EMMA-WATSON-50-SHADES-facebook.jpg


As if to say, "Really? Tinder?".

Alright, damage control mode. You aren't a sexual deviant. You don't agree with judging a girl solely on her looks. You joined simply for a bit of banter with the lads. (All true). Except now she thinks you're like the hoi polloi of Generation Y males; advocating a "hot or not" system of interaction, needing instant gratification through the means of receiving ego-boosting "matches", and willing to fornicate with anyone either remotely attractive or containing appealing orifices. (NB: I'm not claiming to be morally superior in general, just morally superior according to her idea of virtuosity).

So, I look back at her with a look reminiscent of this:

27359039-27359043-large.jpg


I then piss off for a couple of hours, half concentrating on work, half concentrating on how I'm going to Houdini this s**t, and escape with my dignity and self-respect in-tact.

We bump into each other later, and me being my notoriously smooth-as-s**t self, mumbled absolute nonsense for about thirty seconds. After I composed myself, I proceeded to say that "Tinder's s**t, that it degrades women by using them as sexual objects, and that my mates forced me to do it". I actually ranted on about sexual objectification for a couple of minutes (keeping in mind that the people on Tinder actually choose to be there, and in turn, be objectified based on physical appearance), because I thought that's what she wanted to hear. Pathetic, I know.

So, rather than laugh it off as simply a bit of banter between mates, I blamed the app for "being s**t", I went on an over-the-top try-hard leftist rant on the sexual objectification of women, which I only said in some futile effort to impress her, and finally I copped out big time by blaming my mates for "forcing me" to use the app, when in actual fact, it was an agreed upon activity between mates for the purposes of general banter.

I went from having an awesome girl keen on me, to being a clumsy moron with temporary social ineptitude (as you can tell, I experience social ineptitude quite frequently based on my stories on this thread). All this from being found on Tinder. Way to make a simple problem f*cking difficult.

Was not a good day in the life of Croweater. To make matters worse she leaves for the slopes for a couple of weeks, which means that I won't see her for a while. I'll text her during the week explaining everything, but I might have stuffed everything up.

Here's hoping she finds my idiosyncrasies endearing. :$
Click to expand...

This is absolutely dire mate! Good to see the thread back on track though :p
 
Nate7 said:
Wish I found this thread years ago, anyways time to get it out there.

So there I was driving this girl to our 2nd date (met the night before - oasisactive date at her beachshack).
Driving into the Crown carpark (over the speed humps) she pulls it out of my pants and begins deep-throat (I'm still driving at this point) and here I am thinking, "stuff lunch date".
Tickling her vocals all the way to level 3, then had the unfortunate experience of having to walk through Crown to our destination with a raging FAT!

Ok now at restaurant, food arrives - fish tacos for me. Being a classy unit, I came out with, "mmm vertical fish tacos, I hope you taste just like these do!" She finished her meal, got the bill and left, fast. Haven't heard from her since.
Click to expand...
Da hell Nate?
 
Croweater said:
Alright ladies and gentlemen, sadly I have to post in here yet again.

So there's this girl I have a bit of a thing for. I mentioned her a few weeks ago in the "Bigfooty's Guide to Getting the Woman of Your Dreams" thread. Funny, smart, pretty damn attractive. Enjoys beer, wakeboarding and hitting the slopes. Seems interested in me. Well, seemed. Looks: 8.5. Personality: 9.5. A.K.A. girlfriend material.

So we're having a bit of a chat at lunch. She's going up to Mt. Buller for a couple of weeks, so we were talking about that. Another girl who works in the office comes up and we exchange pleasantries. "Oh, by the way, I saw you on Tinder. I swiped right for a laugh". "Haha, oh okay. I never use it anyway. It was only for a bit of a laugh". "Really? When I saw you come up before, it said that you were on about ten minutes prior". "F*ck me dead. Why would you say that?", I thought. "Oh, right..." The girl I'm keen on gives me a look similar to this:

o-EMMA-WATSON-50-SHADES-facebook.jpg


As if to say, "Really? Tinder?".

Alright, damage control mode. You aren't a sexual deviant. You don't agree with judging a girl solely on her looks. You joined simply for a bit of banter with the lads. (All true). Except now she thinks you're like the hoi polloi of Generation Y males; advocating a "hot or not" system of interaction, needing instant gratification through the means of receiving ego-boosting "matches", and willing to fornicate with anyone either remotely attractive or containing appealing orifices. (NB: I'm not claiming to be morally superior in general, just morally superior according to her idea of virtuosity).

So, I look back at her with a look reminiscent of this:

27359039-27359043-large.jpg


I then piss off for a couple of hours, half concentrating on work, half concentrating on how I'm going to Houdini this s**t, and escape with my dignity and self-respect in-tact.

We bump into each other later, and me being my notoriously smooth-as-s**t self, mumbled absolute nonsense for about thirty seconds. After I composed myself, I proceeded to say that "Tinder's s**t, that it degrades women by using them as sexual objects, and that my mates forced me to do it". I actually ranted on about sexual objectification for a couple of minutes (keeping in mind that the people on Tinder actually choose to be there, and in turn, be objectified based on physical appearance), because I thought that's what she wanted to hear. Pathetic, I know.

So, rather than laugh it off as simply a bit of banter between mates, I blamed the app for "being s**t", I went on an over-the-top try-hard leftist rant on the sexual objectification of women, which I only said in some futile effort to impress her, and finally I copped out big time by blaming my mates for "forcing me" to use the app, when in actual fact, it was an agreed upon activity between mates for the purposes of general banter.

I went from having an awesome girl keen on me, to being a clumsy moron with temporary social ineptitude (as you can tell, I experience social ineptitude quite frequently based on my stories on this thread). All this from being found on Tinder. Way to make a simple problem f*cking difficult.

Was not a good day in the life of Croweater. To make matters worse she leaves for the slopes for a couple of weeks, which means that I won't see her for a while. I'll text her during the week explaining everything, but I might have stuffed everything up.

Here's hoping she finds my idiosyncrasies endearing. :$
Click to expand...

For 1) interrupting while you're with another chick, 2) mentioning Tinder, and 3) saying she swiped for you, girl #2 owes you a consolation root. A blowy at the very least.
 
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