Certified Legendary Thread Awkward Flirting Stories

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Jack Package said:
Have been reliably informed that I made a complete moose of myself on about 4 occasions on saturday night, however I was only lucid enough to recall one.

Was at a party and somehow managed to hook up with a girl from high school who I always considered was completely out of my league but at the same time absolutely despised because she was just such a holier than thou bitch (she had had her teeth fixed since then too, so bonus for me).

Started with some small talk about what we had been up to since then and we had done the same course at different uni's so we had some common ground there, then after the shots came out it very quickly escalated to a couple of body shots and a lot of macking on.

Then I all of a sudden decided to blurt out 'You know I f***ing hated you in high school?'... Which in retrospect is probably not the best thing I could have said, but not really a deal breaker I would have thought, we were having a great time and I don't think I said it with a malicious tone or anything. Still silly, but I thought I could salvage it.

Anyway, she got really offended and attempted to push me into the pool, failed and ended up going in herself, completely wrecked herself and hasn't talked to me since.

Left high and dry, quite literally.
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You're avatar is so perfect for this
 
boncer34 said:
I don't remember the weekend New Years but apparently the older sister threw the much hotter younger sister at me who was keen and I knocked her back because I became fixated on the older sister who showed zero interest.

Drunk me is a ******.
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I've done similar before. Had a mate introduce me to two girls who were flat mates, one a solid 8 the other about a 4. I drunkenly assumed the 8 was out of my league and somehow ended up going home with the 4.

The 8 came home a bit later angry at something as she slammed the front door and her bedroom door and was just hating life.

He told me the next day he specifically took me over because the 8 was keen and she was filthy that I went for her friend. I was a bit shattered but as i was ending a significant drought with the 4 I didnt complain too much.
 

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So was conversing with this broad with big boobies in the hope of some fun, while also with this other broad I might be able to get a bit from. both get on the same train, mainly at different times. Well, I was doing good with one on the trip into town, the other got on for the trip out, again I was doing well, this one was quite open they want a FWB, which is why I talk to her.. The next morning there both on the train, sitting across from each other. I decided to sit well away from them.

One picked up on something fishy, the other didn't.

In the local deli in the train station, i asked the sandwich maker if they have gluten free, she explained to me they're having trouble binding the rolls without it, but keep asking. anyway, lovely blonde was giving me big beautiful unsatisfied smiles. This other broad came in, a looker, short denim shorts. While I was checking my phone out of awkwardness as my roll was being made, the broad was watching me instead of making the bloody sandwich. The customer in the denim shorts said as she left "good to see your concentrating on making that roll".
 
little graham said:
So was conversing with this broad with big boobies in the hope of some fun, while also with this other broad I might be able to get a bit from. both get on the same train, mainly at different times. Well, I was doing good with one on the trip into town, the other got on for the trip out, again I was doing well, this one was quite open they want a FWB, which is why I talk to her.. The next morning there both on the train, sitting across from each other. I decided to sit well away from them.

One picked up on something fishy, the other didn't.

In the local deli in the train station, i asked the sandwich maker if they have gluten free, she explained to me they're having trouble binding the rolls without it, but keep asking. anyway, lovely blonde was giving me big beautiful unsatisfied smiles. This other broad came in, a looker, short denim shorts. While I was checking my phone out of awkwardness as my roll was being made, the broad was watching me instead of making the bloody sandwich. The customer in the denim shorts said as she left "good to see your concentrating on making that roll".
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Lara Bingle?
 
Had to turn down a 9 as she was too pissed and I was completely sober.

I can't say the full story as I am still just far too rattled. But heres a taster.

Think of the scene in Wolf of Wall Street where the Duchess gets nude... Pretty much that except I didnt * her...

And yes when I say 9, I mean a real 9, model-type 9. Extras off Entourage 9.
Dutch/American girl working.
 
chunkylover53 said:
Had to turn down a 9 as she was too pissed and I was completely sober.

I can't say the full story as I am still just far too rattled. But heres a taster.

Think of the scene in Wolf of Wall Street where the Duchess gets nude... Pretty much that except I didnt **** her...
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A moment of silence for our brother

50a089e385a40.image.jpg
 
chunkylover53 said:
Had to turn down a 9 as she was too pissed and I was completely sober.

I can't say the full story as I am still just far too rattled. But heres a taster.

Think of the scene in Wolf of Wall Street where the Duchess gets nude... Pretty much that except I didnt **** her...

And yes when I say 9, I mean a real 9, model-type 9. Extras off Entourage 9.
Dutch/American girl working.
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chunkylover53 said:
Cheers lads. Updates will be provided.

Not sure how I'll survive if I don't get it done.

I asked her if I was going to regret that decision and she replied with 'not at all it was really nice of you'.

So here's hoping riding a moral high horse pays off for me.
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You better end up riding HER moral high horse
 
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