Certified Legendary Thread Awkward Flirting Stories

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miss_kate18 said:
Loving this thread. No work is getting done this arvo.

My most awkward attempted pick-up line was as a 19 year old, fresh out of a four year relationship and woefully out of practice. The last time I'd had to flirt I was fifteen and picking up just involved standing near someone at a party and complimenting their music taste.
So, I'm single, finally ready to get back out there and I meet up with a bunch of fellow North supporters at a pub. Most older than me or attached but there's one who caught my eye. Very good looking and more importantly, very funny. I tried to subtly hang out with him all afternoon, made excuses to sit near him etc. At the time I thought I was smooth but it was just amateur hour.

Anyway, I end up next to him (and it's not gone unnoticed that the only other girl there was also giving him the once over). This is my chance to drop a witty, yet sexually suggestive line that's going to make this guy think about me all night. I have the whole world of pick up lines available to me and I go with:
"Your eyes are really nice."

Head, meet desk.
I got a message from him that night though and he admitted the awkwardness was what did it for him.
Click to expand...

North supporter is always a good start.

Start breeding.
 
miss_kate18 said:
Loving this thread. No work is getting done this arvo.

My most awkward attempted pick-up line was as a 19 year old, fresh out of a four year relationship and woefully out of practice. The last time I'd had to flirt I was fifteen and picking up just involved standing near someone at a party and complimenting their music taste.
So, I'm single, finally ready to get back out there and I meet up with a bunch of fellow North supporters at a pub. Most older than me or attached but there's one who caught my eye. Very good looking and more importantly, very funny. I tried to subtly hang out with him all afternoon, made excuses to sit near him etc. At the time I thought I was smooth but it was just amateur hour.

Anyway, I end up next to him (and it's not gone unnoticed that the only other girl there was also giving him the once over). This is my chance to drop a witty, yet sexually suggestive line that's going to make this guy think about me all night. I have the whole world of pick up lines available to me and I go with:
"Your eyes are really nice."

Head, meet desk.
I got a message from him that night though and he admitted the awkwardness was what did it for him.
Click to expand...

Did he have an overly large forehead that you could ski down?
 

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Glacier said:
Pick up lines, oh the memories
I remember a hot young thing in a night club once saying " hi, whats your name?'
My response " ahhh, im ahhh ummm.."
I was so smooth back then
Click to expand...
The kids these days with their mobile phones, tinder and other forms of social media will never understand the awkwardness of trying to chat up a girl in a smoke filled pub or club or even having to ring a girls landline hoping that the her old man doesn't pick up.
 
blueboy25 said:
The kids these days with their mobile phones, tinder and other forms of social media will never understand the awkwardness of trying to chat up a girl in a smoke filled pub or club or even having to ring a girls landline hoping that the her old man doesn't pick up.
Click to expand...

It's as if gen x think we stay permanently inside just locked in our rooms. I face this situation every Saturday. Granted I've never called a landline to chat to a girl, but if I did and the dad picked up I'm guessing I would just say 'can I please speak to xxxx' and it would be over.
 
getthefooty said:
It's as if gen x think we stay permanently inside just locked in our rooms. I face this situation every Saturday. Granted I've never called a landline to chat to a girl, but if I did and the dad picked up I'm guessing I would just say 'can I please speak to xxxx' and it would be over.
Click to expand...
Yep, over for good !!
 
getthefooty said:
It's as if gen x think we stay permanently inside just locked in our rooms. I face this situation every Saturday. Granted I've never called a landline to chat to a girl, but if I did and the dad picked up I'm guessing I would just say 'can I please speak to xxxx' and it would be over.
Click to expand...

But back in the day before mobiles, you had a fixed landline on the wall of the kitchen or wherever it happened to be in your house. You had to stand there and try and chat up a girl while your parents and siblings would be in earshot listening to everything you say.
 
Firstly this is one of my favourite threads, some absolute gold in this.

Felt its time to make a contribution, not a very exciting contribution, but a contribution none the less.

Let me start off by qualifying that i only did what i did because i thought i knew what the outcome would be as i rightfully felt she was way out of my league and to be honest i had never looked at her in any other way than a friend and felt it would be a good joke.

Was back in around year 8 or 9 at High School, a mate of mine had a massive crush one of the girls in our group of friends. He had been talking about her for ages, she was a fairly quiet girl and to the best of my knowledge they hadn't been flirting or anything like that.

Anyway, my mate came back to my house one day after school to play some backyard cricket. During the tea break I decided to log onto MSN and just by chance the girl he had a crush on was online.

As most male teenagers would of done i felt it was a great opportunity to try play matchmaker while he was sitting next to me watching what i was typing but yet he had no control over the content. She didnt know that he was sitting next to me either.

It's important to remember that back then i was utterly shocking with girls that i was keen on, so because i wasn't keen on her whatsoever i had the no fear approach.

So after a bit of small talk and making a few jokes which she responded well too i decided it would be a great idea to stir my mate up and so i asked her the following:

"Will you go out with me" Blunt, straight to the point. He has a bit of a nervous laugh and I'm killing myself laughing as there wasnt 1 part of me that felt the answer would be anything other than a 'no'.

A few nervous minutes go by and we see she is replying down the bottom of the chat box. And you wouldnt believe it but she wrote "yeah i'd love to!" (she was actually serious)

Cue awkward silence at the computer..

obviously my next move was to rectify this but before i got a chance she said she had to go and signed out of MSN.

Mate was a bit bummed. School the next day was fairly awkward as word had spread pretty quick. fair to say that 'relationship' ended the next day.
 
miss_kate18 said:
Loving this thread. No work is getting done this arvo.

My most awkward attempted pick-up line was as a 19 year old, fresh out of a four year relationship and woefully out of practice. The last time I'd had to flirt I was fifteen and picking up just involved standing near someone at a party and complimenting their music taste.
So, I'm single, finally ready to get back out there and I meet up with a bunch of fellow North supporters at a pub. Most older than me or attached but there's one who caught my eye. Very good looking and more importantly, very funny. I tried to subtly hang out with him all afternoon, made excuses to sit near him etc. At the time I thought I was smooth but it was just amateur hour.

Anyway, I end up next to him (and it's not gone unnoticed that the only other girl there was also giving him the once over). This is my chance to drop a witty, yet sexually suggestive line that's going to make this guy think about me all night. I have the whole world of pick up lines available to me and I go with:
"Your eyes are really nice."

Head, meet desk.
I got a message from him that night though and he admitted the awkwardness was what did it for him.
Click to expand...
Glacier said:
Pick up lines, oh the memories
I remember a hot young thing in a night club once saying " hi, whats your name?'
My response " ahhh, im ahhh ummm.."
I was so smooth back then
Click to expand...
The only time I've ever resorted to a pick up line was in Queenstown on a ski trip - very cute brunette American barmaid had been serving us cocktails for a couple of nights running, she was friendly and smiled at me - I'd recently seen Wayne's World and in my inebriated state thought it would be fun to drop Garth's amazing line "if you were president you'd be Baberaham Lincoln".

Much to my surprise it worked a treat!

s**t story for this thread I know but I'll take it!

Sent from my Nexus 7 using Tapatalk
 
blackshadow said:
The only time I've ever resorted to a pick up line was in Queenstown on a ski trip - very cute brunette American barmaid had been serving us cocktails for a couple of nights running, she was friendly and smiled at me - I'd recently seen Wayne's World and in my inebriated state thought it would be fun to drop Garth's amazing line "if you were president you'd be Baberaham Lincoln".

Much to my surprise it worked a treat!

s**t story for this thread I know but I'll take it!

Sent from my Nexus 7 using Tapatalk
Click to expand...
Baberaham....love it but never ever thought anyone would use it.....well done sir
 

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Michaels said:
Firstly this is one of my favourite threads, some absolute gold in this.

Felt its time to make a contribution, not a very exciting contribution, but a contribution none the less.

Let me start off by qualifying that i only did what i did because i thought i knew what the outcome would be as i rightfully felt she was way out of my league and to be honest i had never looked at her in any other way than a friend and felt it would be a good joke.

Was back in around year 8 or 9 at High School, a mate of mine had a massive crush one of the girls in our group of friends. He had been talking about her for ages, she was a fairly quiet girl and to the best of my knowledge they hadn't been flirting or anything like that.

Anyway, my mate came back to my house one day after school to play some backyard cricket. During the tea break I decided to log onto MSN and just by chance the girl he had a crush on was online.

As most male teenagers would of done i felt it was a great opportunity to try play matchmaker while he was sitting next to me watching what i was typing but yet he had no control over the content. She didnt know that he was sitting next to me either.

It's important to remember that back then i was utterly shocking with girls that i was keen on, so because i wasn't keen on her whatsoever i had the no fear approach.

So after a bit of small talk and making a few jokes which she responded well too i decided it would be a great idea to stir my mate up and so i asked her the following:

"Will you go out with me" Blunt, straight to the point. He has a bit of a nervous laugh and I'm killing myself laughing as there wasnt 1 part of me that felt the answer would be anything other than a 'no'.

A few nervous minutes go by and we see she is replying down the bottom of the chat box. And you wouldnt believe it but she wrote "yeah i'd love to!" (she was actually serious)

Cue awkward silence at the computer..

obviously my next move was to rectify this but before i got a chance she said she had to go and signed out of MSN.

Mate was a bit bummed. School the next day was fairly awkward as word had spread pretty quick. fair to say that 'relationship' ended the next day.
Click to expand...

A 'maybe' box could have bought you some more time in this story.
 
blackshadow said:
The only time I've ever resorted to a pick up line was in Queenstown on a ski trip - very cute brunette American barmaid had been serving us cocktails for a couple of nights running, she was friendly and smiled at me - I'd recently seen Wayne's World and in my inebriated state thought it would be fun to drop Garth's amazing line "if you were president you'd be Baberaham Lincoln".

Much to my surprise it worked a treat!

s**t story for this thread I know but I'll take it!

Sent from my Nexus 7 using Tapatalk
Click to expand...
Baberaham....love it but never ever thought anyone would use it.....well done sir
 
blackshadow said:
The only time I've ever resorted to a pick up line was in Queenstown on a ski trip - very cute brunette American barmaid had been serving us cocktails for a couple of nights running, she was friendly and smiled at me - I'd recently seen Wayne's World and in my inebriated state thought it would be fun to drop Garth's amazing line "if you were president you'd be Baberaham Lincoln".

Much to my surprise it worked a treat!

s**t story for this thread I know but I'll take it!

Sent from my Nexus 7 using Tapatalk
Click to expand...
Baberaham....love it but never ever thought anyone would use it.....well done sir
 
Glacier said:
Baberaham....love it but never ever thought anyone would use it.....well done sir
Click to expand...
I'll keep it as a one and only success!

Sent from my Nexus 7 using Tapatalk
 
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