Epic fail flirting stories

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Eleuthera

Let slip the Guinea Pigs of war!
Sep 11, 2008
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Two occasions spring to mind.

The first has been mentioned before, I got turned down for being too nice. The only "nice" thing I did was lend her my lighter...

The second happened about a year ago. I'd been talking to a girl for a while, when she had to go home with her friend. I was a bit late with the exchanging numbers thing so I only gave her mine and didn't get hers. I discovered 2 days later I gave her the wrong number...
 

Low Key

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May 7, 2009
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Me, my friend, his sister, and her boyfriend were all at a club. My friend told his sister's boyfriend that I had been single for quite a while, so all of a sudden, he's chatting up this girl, telling her about me and whatnot. Whatever, cool, I can work with that, even though I wasn't planning on it going very far. But because I had had too much to drink that night, when she asked "What brought you guys downtown tonight", I immediately piped up and said "We came to watch my friend's ex-girlfriend strip". There was a strange awkward silence and she walked away. Funny thing is, it was 100% true. I thought women appreciated the truth. haha

But all in all, she wasn't my type, at least from the description my friend's sister's boyfriend gave me. I could tell she was a bookworm and far too intellectual for me. Not saying I'm not intellectual, I just prefer my women to put the smarts on the backburner and let loose (not as loose as my friend's ex). Besides, when I'm sober, I do a million times better picking up women. Liquid courage doesn't work for me.
 

manicfoot

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Apr 16, 2008
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I'm oblivious to flirting. One time I was in a pub with my friends and went to go to the toilet and said "excuse me please" to these girls who were in my way. Went back to my table, carried on getting drunk. When we were outside I was joking around with my friends and one of the girls was there too and she said "move your hair away from your face so I can see what you look like..." and I completely ignored her :S Still feel really bad about it. She must have felt stupid :(
 

Lord Thodin

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Jul 1, 2009
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I got one that'll make you gringe.

It was the 4th of July. There was an open fireworks show at this large beach where i live. I went with some friends and this girl i didnt know but they were friends with. Needless to say she took a shine to me and i was quite fond of her. The night progressed and i made jokes, she giggles and we cuddled watching the fire works. It was all going swimingly, then while we were walking back to the car i decided, instead of leaving now, why not wait for the sea of people to subside. So we did and me and this girl continued flirting however. I lost my suave. we were talking and "play" arguing id guess you call it and we pressed out foreheads together. I was considerably taller than her so i had to bend down quite a bit. Well from my angle it looked like she had a old 1970's porn star stash because the way my hair was in my eyes in correlation with her face. So i actually blurted out "You know, from this angle, you have a mustache.." She just sat there mouth agape then walked away with my friend who drove us there laughing his ass off at me............i think a little of me died that day
 

Baris345

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Aug 3, 2009
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Hmm, mine feels kind of timid compared to some of the more embarrasing ones posted.

About a month back I was visiting my half sister who lives in Turkey and only speaks Turkish, the language which I've basically completely forgotten thanks to living in Ireland for 8 years.
Since she was graduating the week I spent with her there was a lot of drinking everynight and I started to really like her best friend, whom I eventually confessed to after many beers. At which point everyone we were with at the bar (7 friends of my sister who also speak very little English) broke into laughter, it was still going on after a whole minute and I excused myself to take a piss.

To this day I have no idea what I said.
 

Insert Comedy Here

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May 22, 2009
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Don't know if this counts but...

Walking right past a group of girls that were pretty much screaming out my name, not the best way to endear yourself to the women.
Also, I was listening to my Mp3 player at the same time, at decently loud volume, so they must have been screaming 'blue murder' for me to be able to hear and ignore them.
 

gewuerzgurke

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Jun 29, 2009
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I was in a bar in France with some friends. We saw a really good looking guy, and as he was talking french to his friends, we supposed he was french, and talked in german about how extremely hot he was. At some point he turned around and said "oh, so you're from germany aswell?" That was VERY embarassing. It turned out that he was half french half german. Nevertheless we spent some very funny nights with him.
 

Trivun

Stabat mater dolorosa
Dec 13, 2008
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Cpt_Oblivious said:
King_Paco said:
singing to a chick while under the influence is a horrible way to go.
Only if you're bad at singing. It worked when I sang a disney song to one girl.
If it's from the Golden Age then any Disney song is straight away acceptable. Provided you can sing. If so, then go for it... (starts humming Circle of Life)... hmmmmmmmm

Ahem.

Anyway, moving on. I don't have any funny stories because I'm too shy to chat girls up, I usually wait for them to make the first move. Which usually never happens. The one time I did make the first move it went well until the girl in question had to go back to her home in Scotland. Fortunately we're still friends though :)

However, I did once muck things up with one girl who was actually the ex of another friend. I'd actually met her only once before when they were together, then we got in touch when they split up. Anyway, she came over to my house once and we went out, but again my crippling shyness kind of drove her away. I really need to get some more self-confidence...
 

dwightsteel

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Feb 7, 2007
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Trivun said:
Cpt_Oblivious said:
King_Paco said:
singing to a chick while under the influence is a horrible way to go.
Only if you're bad at singing. It worked when I sang a disney song to one girl.
If it's from the Golden Age then any Disney song is straight away acceptable. Provided you can sing. If so, then go for it... (starts humming Circle of Life)... hmmmmmmmm

Ahem.
I know for a fact that "A Whole New World" is effective. And I won't go into details, in what is probably the most humiliating episode of my life. Just take my word for it: You can't go wrong with "A Whole New World".
 

maddawg IAJI

I prefer the term "Zomguard"
Feb 12, 2009
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I had a friend who started flirting with this girl who sat next to him in Geometry (Becuase it always happens in Geometry.) Anyway he gets shot down multiple times. After about two weeks of trying he came into home room one day looking like he saw a ghost. He tells me that he went to a family party and found out that the two of them were related.

Basically he spent two weeks trying to hook up with his cousin.
 

Emeli

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Mar 9, 2009
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Fat Man Spoon said:
Walking over to a girl and getting hit in the face with a football halfway there.
I can one up you. While I was lost in my crushes eyes and he was smiling at me a dog came out of nowhere, knocked my knees out from under me and then slobbered all over me while I lay ont he ground.
 

Dyp100

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Jul 14, 2009
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maddawg IAJI said:
I had a friend who started flirting with this girl who sat next to him in Geometry (Becuase it always happens in Geometry.) Anyway he gets shot down multiple times. After about two weeks of trying he came into home room one day looking like he saw a ghost. He tells me that he went to a family party and found out that the two of them were related.

Basically he spent two weeks trying to hook up with his cousin.
Oh God. >.> That must be horrible.

I've got a GF and never flirted, I fail, but I love these threads.
 

Erana

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Feb 28, 2008
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Once, I was sitting outside of the coffee shop, my nose in my school books, and this guy kept trying to talk to me in this almost stuttering tone. I'd been in a bad mood that day, so I kept shrugging him off, agitated. Eventually he tried to extend his arm for a handshake and he knocked my hot tea onto my lap. I left, flustered, and didn't say a word.
Apparently the poor boy was a friend of a friend, we had actually met before (I thought he was just trying a bad pickup line), and he was just trying to ask me to go to a gallery downtown to go see a local band I had voiced some interest in.
Fail from both parties... >.<
 

maddawg IAJI

I prefer the term "Zomguard"
Feb 12, 2009
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Dyp100 said:
maddawg IAJI said:
I had a friend who started flirting with this girl who sat next to him in Geometry (Becuase it always happens in Geometry.) Anyway he gets shot down multiple times. After about two weeks of trying he came into home room one day looking like he saw a ghost. He tells me that he went to a family party and found out that the two of them were related.

Basically he spent two weeks trying to hook up with his cousin.
Oh God. >.> That must be horrible.

I've got a GF and never flirted, I fail, but I love these threads.
Actually it gives me a little thing I can hold over his head.
 

Hikikomori Ookami

New member
Jun 26, 2009
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TaborMallory said:
Being nice.
Seriously.

I was turned down 9 times last year for being nice. Not creepy nice, or overly nice, or whipped. Just average nice. Goodbye, self-esteem.
I hate hearing that one. Used to happen to me all the time too, then I turned into a bitter ass hole (from unrelated events) so at least I don't hear that anymore.
 

Fulax

New member
Jul 14, 2008
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Last year a friend of mine walked up to a girl in a bar on a student's night out. They got talking and she asked him what he was studying. He said Computer Science. She immediately walked away.
 

Antlers

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Feb 23, 2008
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I used to tell people I did Science instead of Engineering. Unless I thought I'd like to progress our relationship beyond that drunken night in the pub.
 

Dottie

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May 6, 2009
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savandicus said:
Card tricks are a great way to get into a conversation with someone your interested in, they grab attention, sometimes impress and allow you to break the ice so to speak.

You just have to use them to get things going and then move on from there.
Sounds like you read that straight out of a book. It doesn't work that way...EVER.