Certified Legendary Thread Awkward Flirting Stories

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I remember this when I was younger. Took a girl I was keen on to a John Mayer concert at the Belvoir Ampitheatre (Amazing venue). I was probably 16/17 and things were starting off well but of course a fellow girl in our year and her boyfriend ran into us and decided to sit right next to us and just ruined the whole night. She wouldn't stop talking!

More of a 'cockblocked by yappy teenager' story than an awkward flirting story
 
Hmm where do I start?

I was a fairly shy teenager, and still kind of am. Am still useless with female clues, but don't seem to have much trouble these days.

Anyway, I think it was year 9 or 10.

This girl started initiating conversation with me, and for a number of weeks we had been flirting. Talking each time we saw each other before going into class etc.

Anytime her friends and her walk past me, they would look and giggle etc etc. I found this pretty weird. :confused: Didn't do a whole lot for my awkwardness and so on.

Anyway, the conversations continued for a number of weeks. I didn't suspect a thing. I was pretty oblivious to anything happening in this class we shared as well.

One day the teacher got me to hand back tests to the class or whatever. Handing out the papers to those I knew in the class without calling out their names. It came to hers and I read out her name, as I didn't know it.

She gave me this laughing cringe as I handed her test back, and as I walked past to the next row of desks, I hear this laughing from her friends and her saying, "he doesn't even know my name!"

She was very very fine and she never spoke to me ever again.

Not even 4 years later when I got out of my car to help someone push theirs to safety. Unbeknownst to me it was her until I got to the car, and she did not say a word. Not even a thankyou. Just a point where she wanted the car to go. :eek:

And a shake of the head when I asked if she wanted me to wait or to do anything else. :eek:

Her disdain was still palpable. And she was even better in the looks department at this stage. Probably model quality.

Subsequently, I have never forgotten her name. :eek:
 

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I'm waiting for a female to post....

..."so I was willing to give it up and go mental on the next bloke that come across that wasn't a loser like my ex. So my friend hooked me up with a guy from her work, who rocked up to my house thinking he's top s**t because he lives with 8 feral housemates, and only calls his parents to borrow money. And to think I was nearly going to blow this guy before he bagged my job and dropped me back at home?"



We just had our xmas party, and this thread (and the Seinfeld episode where Jerry tried to talk dirty) immediately come flooding back. Whilst we have mostly a mature staff, a couple of the younger brigade provide us with entertainment at events where alcohol is provided. Although I was not witness to these events, the story relayed back still had me in tears. Two recently single again staff members were not very subtle in their flirtations at our recent function, very early on in the piece (I was still there, so it was definitely early). 3 hours later things still looked cosey, and the young lad was spotted walking to the gents looking quite triumphant, while the young lass looked a bit bewildered, horrified, and then left with a couple of other girls. Long story short, their chat lead to conversational foreplay, until the young lad found himself short of flirtations. Apparently his final sexy remark was "well, I guess I better rearrange your uterus with my fist!" After she left this young bloke apparently drank himself into obliteration after realising what a creep he sounded like.
 
I hooked up with a bird a couple weeks back at a pub but nothing went further that night. We exchanged numbers and kept in contact. It fairly quickly took a dirty turn and some graphic messages were sent by myself and the other party throughout the week. All I will say is it is always good to check a message before you send it, and auto text can cause issues. Telling a girl you want to lick her pussy is one thing, but when autotext changes this to "I want to kick your puppy" it is not an ideal situation.
 
I hooked up with a bird a couple weeks back at a pub but nothing went further that night. We exchanged numbers and kept in contact. It fairly quickly took a dirty turn and some graphic messages were sent by myself and the other party throughout the week. All I will say is it is always good to check a message before you send it, and auto text can cause issues. Telling a girl you want to lick her pussy is one thing, but when autotext changes this to "I want to kick your puppy" it is not an ideal situation.


classic auto correct is classic
 

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Especially if your mate catches you pounding her in the toilet at a mutual friends BBQ.

Well done. You've annoyed my wife by causing me to chortle while she's 'trying to watch this!' :D
 
Well the other day I saw this woman walk past me, she was like one of those figure fitness type chicks totally toned, I was like holy crap, probably in her late 20s early 30s, but totally the sort of chick I'd go for. I was kicking myself for not doing anything about it, but anyway the next week I thought I'd just see if she passed by, and yeah I saw her, I couldn't remember the last time, I'd made some sort of effort like this, anyway I was a bit slow, and walked into her office building, I had just started to talk to her, and noticed she had a wedding ring on. There was a moment of awkwardness for what seemed like an eternity, until I just pretended to walk up the stairs, and waited for her to catch the elevator, then walked out. It was kinda embarrassing but at least I'm not going to die wondering. The funny thing is for 15 minutes prior I was pumping myself up doing pushups etc so I could look a bit more built, what a *ing waste of time that was, i felt like a complete ass.
 
I had a few people over at mine one night, anyway I was getting bored and tired so went to bed, few minutes later this bird walks in my room strips naked and gets into bed with me, being the gentleman I am, I gave her an extra blanket so she wouldn't get cold, rolled over and went to sleep. Did I miss a chance here?
 
I had a few people over at mine one night, anyway I was getting bored and tired so went to bed, few minutes later this bird walks in my room strips naked and gets into bed with me, being the gentleman I am, I gave her an extra blanket so she wouldn't get cold, rolled over and went to sleep. Did I miss a chance here?

Clearly not interested.
 
I have been racking my brain to think of an incident where I've skew-iffed it, but I am a man of little moral fibre, and was told by a wise British gent I worked with as a young fella three pieces of advice, which are basically that same thing worded differently, and I've lived by ALL of them for the past 12 years.

1. A faint heart never f**ked a fair lady

2. The one you knock back is the one you miss out on.

3. Any port in a storm

Having said that, NYE 2010, freshly single from a 3 year relationship, starting to get that swagger back. We hold a NYE party for the footy club at our palatial digs in way west Sydney, good crowd, about 50 or 60 of us. A mate's missus brings a bird that is beautiful, I'd reckon an 8. Really nice to talk to as well, had a bit of a flirt previously. So yeah, I'm thinking I'm half a shot.

So I get stuck into my poison of choice - Cointreau. I can't drink dark spirits and got hooked on the french jooce as a young tacker. Nice warm day, cricket in the street, international beer drinking contest between the boys.....yeah.

So the mate, his missus and friend arrive, just before sundown. Sweet, she looks gorgeous, gives me a hug n kiss. Yeah. Mind, I'm drinking strong for the past 4 hours, had a few blasts on the ganga, as you do. Things start going from clarity to small, photo like instances. Scenes missing, if you will. We sit down next to each other around the table. Asks how I am after break up; small talk. I open up a bit (The break up was all my doing, boss like) and we chat and laugh for awhile. She puts her hand on my leg. I am fecking ready to go. I notice a big ring on her finger. BIG. So in my coolest voice, I say 'Dear lord, did you rape Liberace for that ring?' and laugh to myself. She peered beyond my soul. I look around the table of all the footy boys: three is in hysterics, one is giving me the wind up, everyone else had that 'you didn't just say that did you?' look on their face.

She utters something and goes and stares at the garage door until I disappear upstairs. Few more hot ones. Fell down the stairs. Vomited in my hands. Brother carries me upstairs. Wake up in the bath. And, due to my love of Cointreau, I bite people. Hard. I near severed her cheek.

Fear not, I am not forlorn! I will make up for it. But the boys do call me Libba at footy from time to time.

Only bonus out of it, if any, was the Blues Brothers marathon on Fox that day. Every so often I'd think about how I managed to **** block myself with a reference to the equally-est flaming piano player in music history. Yeah.

I am loving this thread too.
 
Okay. Firstly, this is an amazing thread. So much fail haha.

I have a decent one, not 100% my fault, but certainly copped bucket-loads of s**t about it off mates, and still do occasionally - some 2 years on.

Having a sister two years younger than me has always provided me with any number of her friends to chat up with an easy starting point. Though she has this one friend, who is an absolute 10/10, and I barely ever even considered it to be the faintest possibility. Until one night at a nightclub, I told my sister how amazing her friend was. My sister (a solid wing-woman in her own right) went over and told her friend god know's what, but her friend came over on the dance floor, smiled and started kissing me straight up. We spoke for a while after this and hooked up several other times that same night. Exchanged numbers, but I didn't contact her at all for a couple of weeks.

Cue the night of the fail...

A fortnight later I went to the train station to head into the city, and she was doing the same, both on our own. She teased me about not contacting her and we flirted the whole way to the city on the train. She asked me to come to the club she was going to with her mates, but I had prior arrangements I was obliged to honour. She messaged me almost instantly after we got in separate taxis telling me she wanted to catch up later and had an hotel room with her guy mates, but would prefer to stay elsewhere.
I went to my mate's event, got sh*t-faced, messaged her several times during the night and she was keen, my phone was going flat though so I turned it off to save power. I got too drunk, forgot to turn it back on until 4am, at which point I had numerous messages/missed calls from her asking when she could see me/stay with me. I apologized but got no reply, didn't see her for two weeks, in which time she started dating a mate of mine (broken up now, but were together for over a year) and is now off limits. I have never lived it down.

Not sure why I said it wasn't all my fault, in hindsight - massive fail.
 
What the hell dude.

Let's turn down obv sex with a 10 to get wasted with my mates, something I can do every weekend.

So bad :D
 
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