Certified Legendary Thread Awkward Flirting Stories

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Kissing ok. The full on practically dry humping umm no. # itsokiknowimananna

Dry humping is harmless, don't see the big deal.

I didn't do anything worse until 15.
 

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Hold the press.

I'm out at the moment with several mates, and a guy and a girl here used to casually f*ck. She's here with a guy she's been seeing, oh I don't know, maybe for a month?

We were just talking about being photogenic and my mate interjects: "Yeah, like that time you sent me those nudes!". We've all had a few and he's no exception. He realised what he said and tried to play it off as a joke, but her obvious embarrassment and our tacit "Oh my god, I can't believe he just said that" reactions kind of gave it away that he wasn't kidding.

Awkward as f*ck. :eek:
 
Many years ago:

After a night at a club, we picked up a lady and went for a drive. There were four males and just the one lady.
I don't know what got into us but everyone in the car got a little excited and we all took our clothes off.....but once we did, we sort of got stuck and just looked at one another not knowing what to do next.
It was the most awkward of moments looking at your mates naked and this one lonely lass but no-one prepared to get the ball rolling......nothing happened and we all put our clothes back on and drove home......awkward.
 
We were just talking about being photogenic and my mate interjects: "Yeah, like that time you sent me those nudes!". We've all had a few and he's no exception. He realised what he said and tried to play it off as a joke, but her obvious embarrassment and our tacit "Oh my god, I can't believe he just said that" reactions kind of gave it away that he wasn't kidding.
Hah, I rate that.
 
That reminds me of a particularly odd episode.

My mate had just bought himself his first home at 20 and we frequented the place regularly.
He had a large piano in the lounge room for some reason and on this one night, he, a lady friend and myself had indulged quite a bit and for reasons still unknown to me, we all undressed and sat on the piano bench and played the piano together.
I know we laughed ourselves silly, but have no recollection of anything thereafter. Maybe that's a good thing......never asked about that night, since.
 
I finally remember a moment where I can contribute to this thread.

2am, me and 2 friends head down to a bar being about 10 to 12 drinks deep, so safe to say pretty drunk at this point.

Have one or two more drinks there, and I'm drunkenly stumbling throughout the bar. I happen to see my 2 friends dancing with a group of girls so I walk up and start dancing too somewhat on the outskirts of the circle.

The next thing I remember is a girl walking up to me and saying something along the lines "can you please leave us alone you're creeping us out standing there".

I sort of wake up at this moment, confused as to how long I've been standing there. My mind went from * you, to wtf is going on, wait where did my friends go, and how long have I been standing here?!?

Confused and lost for words I just drunkenly walk away.

In hindsight, I'm fairly sure my friends did not go to those group of girls at all in the first place.
 
Hold the press.

I'm out at the moment with several mates, and a guy and a girl here used to casually f*ck. She's here with a guy she's been seeing, oh I don't know, maybe for a month?

We were just talking about being photogenic and my mate interjects: "Yeah, like that time you sent me those nudes!". We've all had a few and he's no exception. He realised what he said and tried to play it off as a joke, but her obvious embarrassment and our tacit "Oh my god, I can't believe he just said that" reactions kind of gave it away that he wasn't kidding.

Awkward as f*ck. :eek:[/QUOTE
Well what did everything think this couple were doing while they were doing the horizontal tango? Holding hands and looking at the stars? I don't get why so awkward? Why hang out with people you used to bonk casually anyway?
 

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Yeah but that's what I mean....they used to ****, she used to send him nudes, who cares? It's now probably more normal to send nudes than not send nudes.

NUDES

Yeah that's not awkward- I'll tell you what's bloody awkward. Giving the "live show" version of nudes to a guy off BF.

Involved a pool, ill fitting swim suit and myself.

That's awkward. :$:$
 
What?! 'splain yourself ploise.

Nothing much really.
Group of mates from Geelong- one couldn't make it to dinner, so I said come around to the hotel, for beers and hang by the pool. (was summer)
I knew the bikini didn't fit me properly, but I was making every effort to remain modest.
I obviously didnt do a good job because I got this text later that arvo- "Um, I'm sorry to say this but you know I could see your nipple a couple times lol".
-spent next 10 mins almost having a meltdown/breakdown-
Then just laughed it off and its like Rachel from Friends: "it's ok i have nice boobs" and moved on.

I'll tell you something I wear a tank top now with that swimsuit.
 
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