Describe An Embarrassing Example of Trying To Pick Up Someone

So we've all tried different things to try to pick up women, men, both, or 'other' (whatever floats your boat). Sometimes these techniques work really well. Others...well, yikes. And then there are others that are amazingly embarrassing. These are the ones I'm interested in. So...share away.

Here's mine. It was at my first job. I had been there for a few months and we had just hired a few new employees. Two are relevant to this story; a guy and a beautiful woman. The guy...was, well, nice enough I guess. But he and I were both attracted to the new girl. So we spent a few weeks trying to muster as much game as we possibly could. This was rough considering that neither of us had any game to speak of. But we tried. Well, one day I decided to try to really impress her. I had a really good day of working my 'game' (it wasn't very good looking back now) and I thought we were really going somewhere. Then, I saw opportunity rise. I needed to flip a couple of fuses that corresponded to lights where I was working. I worked in a 'family fun park ' that had bumper cars, lazer tag, batting cages, etc. I was working the batting cages. The fuses were inside of the bumper car area (caged by a metal fence). Every night I worked in the batting cages I was required to turn on the outdoor lights. I had learned a 'really cool way' to enter the bumper car area to flip the fuses. I used to jump over the metal fence, land in the bumper car area, and flip the fuses. Simple, right? I had done it many times up to that point. Well, this day I decided to do this stunt extra well to impress 'my girl'. She was running the bumper cars and I thought, "I'll really impress her by jumping over this fence like a bad ass!" Because, women are impressed by stuff like that right? Well, I did it. Then I fell and every single person in the entire place heard and stared at me. This included 'my girl'. That night, I offered to walk some of my employees to their cars (it was something the bigger guys did every night by order of management). I had hoped to walk 'my girl' out to her car and turn what happened into a joke so that she might...I don't know, sleep with me (that's where my head was as a high school student). Well, remember the guy I mentioned earlier? He walked them out including 'my girl'.

Fuck.

I once clubbed a chick over the head to assert my manliness. Apparently people don't do that anymore.

Picking up a little person. Enough said.

I touched this girl's shoulder once. She just stared until I ran away.

I seem to never be able to tell if a girl is flirting with me, or making fun of me. Or I get them switched every time. Ends with me being defensive when they do flirt, and *cough* "smooooth" when they aren't flirting.

Fuck all that noise.

Or just fuck girls.

More guys should hop fences for pussy, is the message I'm trying to convey.

@jyluth:

You're right, that is creepy.

I once told this girl she was "making it hard for me", I should've kept my mouth shut and just kept staring at her. I wanted to tell her that her beauty was beyond compare and that for me to keep quiet about this was...

You know the rest. What makes it even worse is that she was super sweet about it and smiled then told me I was sweet, like I was her friends disabled brother or some shit. I'm embarrassed just thinking about it. I need a beer.

@crazyleaves said:

I once told this girl she was "making it hard for me", I should've kept my mouth shut and just kept staring at her. I wanted to tell her that her beauty was beyond compare and that for me to keep quiet about this was...

You know the rest. What makes it even worse is that she was super sweet about it and smiled then told me I was sweet, like I was her friends disabled brother or some shit. I'm embarrassed just thinking about it. I need a beer.

...I'm not sure staring at her would have been much better. That sucks though dude.

I once got called a tyrant by a woman after I pointed out that I enjoyed watching people dance from a balcony in a club.

@JasonR86: Well I wasn't really staring, I was "checking her out" as is the parlance of our times.

@Undeadpool: You are! You're an unspeakable cad!

Not really too embarrassing, but I asked out a coworker on her last day of work thinking I had nothing to lose if she said no because I'd never see her again. Of course she said no, but unexpectedly she came back to work a few months later. Now we have a few shifts a week together and it's just Awkward City and I'm the mayor.

One time I escalated before negging.

@Undeadpool said:

I once got called a tyrant by a woman after I pointed out that I enjoyed watching people dance from a balcony in a club.

Heh. That made me chuckle.

I started small talk with this girl at a bar then when I proceeded to ask for her number she told me my friend was more cute. Ouch. =/

I laughed it off and had fun with my friends and talked to other girls.

i dont really have any embarrassing stories to tell atleast i cant remember them.

i cant tell if girl are flirting or interested in me, apparently there was this smoking hot girl i was friends with that i kinda had a crush on but got the feeling that she only wanted to be friends. found out maybe 4 years later that she had a crush on me and have had for the last year. so basicly it ended with nothing.

and i dont know how to "pick up" girls either, i really dont try all that much, but when i drunk or mildly drunk i aparently got "mad skills" that i never can remember all my relationships since i was 16 has started with alcohol

Never tried before. I know I don't have a chance in hell for them to say yes, so there is no point in trying.

Well, I guess there was the time I asked the girl to prom but it wasn't anything more then us being friends and her saying yes out of pitty because she knew no one else would go if she didn't offer. Anyway, she basically told me to ask her out to the prom and she would say yes through a friend of a friend kind of thing, and I didn't find out until after the fact that she was actually dating another guy in the same class as me at that time. As far as I know he didn't care since he had already had plans for years to go with someone else, some family thing iirc, but it was weird doing the slow dance and stuff with her boyfriend not far off and her running off to go talk/hang out with him in between all the scheduled nightly events.

All and all it was a really painfully awkward and terrible night that I wish I had never gone through, but the only reason I did was for my mom. At this point she was in the last year of her life, she was hospitalized and stayed in there for the last few years she was alive because she couldn't be at home, and all my life she talked about wanting to see me graduate and go through all the usual graduation ceremonies so I just went through it for her. We didn't know at the time that she was going to die the next year, but she lasted long enough to at least see me get out of High School and a year into college. At least she died thinking I was doing something with my life and she didn't get to see the joke that it has become after.

I don't trust pretty women, so I've made it my agenda to humiliate, offend, and break the hearts of as many of them as I can. I have no problem picking up women and I do so quite regularly with the intent to break their hearts. So fear not brothers and sisters for each painful rejection you have faced I have slept with a hot women and tossed her to the side like a mere play thing, leaving her confused and her ego bruised. You can have your vengeance vicariously through me.

@mlarrabee: Sir! You insult my honor! We shall dual with fountain pens at forty paces!!

I take offense to this "other" comment :|

Funny story....

I was at a Reel Big Fish concert with my friend, and we were rolling our balls off on ecstasy, which makes you really horny as well as relieving you of any inhibition whatsoever. As I make my way out of the skanking pit dripping with sweat and with pupils the size of nickels, I find a nice spot outside the crowd where I can take a quick breather and enjoy the music. There's a girl next to me, she's got a bit of a gut, but my lower-than-low standards coupled with the drugs made me ignore it completely. It's funny how being under the influence changes your confidence, because sober I'd have just left her alone. That night all that was going through my head was "Dude, she's fat, you could totally get with her!"

And what was my award-winning Casanova line? "What's your name?" She just looked at me like I raped her puppy. An expression of genuine fear and anxiety, followed by her weakly mumbling her name, pulling a 180, and walking back to her friends. It doesn't sound like much, but when I tell that story to people that know me they tend to laugh because I'm such an awkward mess around women, even when I'm fucked up.

In my first year of uni I often ended up in the possition of sleeping with girls before chickening out. My very first night I went to the student union with some people from my building after a party. One girl had been sticking close to me all night, shared her wine with me and was generally being lovely. We ended up seperating from the group who were a bit drunker than us and I invited her back to my flat, with the pretense of, 'a cup of tea'. She sat on my bed and I put some music on. I swivelled arround on my office chair to look at her, planning to kiss her. I lost my nerve, stood up and said 'I'll just put the kettle on...'. I believe she took offence as she wouldn't talk to me after that.

Later that year I failed to realise that when a beautiful girl from Hong Kong askes for help with her assignments every day, regularly gets into your bed, knocks on your bedroom window to talk to you and drapes herself over you in bars; she probably wants to sleep with you.

On a seperate occasion I vomited while making out with a second year in a night club.

It is unclear how I have managed to maintain my current relationship for ten months.

I saw this beautiful chick in a club and I slid up to her and said "You're so pretty, I bet you've had loads of abortions." which is my most flattering chat up line.  She said "No I haven't, but I've performed loads of them!"  We both laughed and went home and did loads of sex.  In the mouth, up the chutty, in a paddling pool out the back... anyway and you wouldn't believe it, but she was only my mum!

@jyluth said:

On a couple occasions I've had men follow me home from late evening trips to the corner store. I suppose that's a bit more creepy than it is embarrassing.

I really just wanted to say hi, I promise :( I am shy.

while yes i do. it was pretty funny one.
 
it was june. my friend and his family invited me to go on a cruise. i went on the cruise. one time during dinner my friends and i saw these three hot girls eating. we decide that once they get up we will follow them. we follow and then a big group of people come so we lost them. we decide to split up to find them. i find them and my other friend went somewhere else. i start talking to them and then i saw my friend. we start talking and it was awkward to talk to them. we finally ask their age and to find out that they were 15 and 16, and then i said, i have to go. i was 23 at the time.

Every time i try!

When this one girl clearly wanted me to do something and got drunk.  She then took off my fitted cap and put it on her own head.  If you own a hat you would know what this means.  I guess that was a sign but being the big dummy that I was, I didnt do anything.  

it's just Awkward City and I'm the mayor.

@the_OFFICIAL_jAPanese_teaBAG: I'm definitely missing something here. Perhaps it's because I don't own a hat, so I don't know what it means. :(

I've never really had an embarrassing failure or whatever you wanna call it, mostly 'cause I only am the most awkward guy ever and I only ever try anything if I am certain.

Although, I have realised, whenever I'm walking along, through town let's say, and I see an attractive lady, instead of like popping a sly smile or something, I'll do something nervous looking glance thing and have a somewhat pained expression on my face as I do whenever I walk through crowded places. I can only imagine what kind of psychopath the ladies in my city think I am.

In middle school I was skating down the street and saw two hot girls on a nice walk. I skated up to them (skateboard) and was just coasting next to them trying to talk them up and not paying attention. After a couple min I ran into a parked car and fell off my skateboard, not in a graceful way. The girls busted up laughing and kept walking while I chased down my board....I decided to keep a small sliver of my dignity and just went the other way once I caught my board. Another time we had met these girls at the skatepark, pretty good lookin chicks. One of them was out of this world hot though, and her friend told me later that day that she wanted to hang out with me. We hung out three or four times, just being flirty and getting to know eachother. Fast forward a week or so and me and my moron friends are at the skatepark again just hanging out, and we decide to do the gallon challenge (drink a gallon of milk in under 45 min). Naturally after about 30 min I fire hose vomit all over the place. About 5 min later the girls showed up and Maggie asks me to come with her because she wanted to talk. We go get in her car and she immediatly starts making out with me. There was nothing I could do to stop it and it was totally unexpected, plus she was super hot so I just kinda went with it.....she didnt call for about 4 days after that, so I called her friend to see what was up. She told me that Maggie said I tasted like sour milk when she kissed me lol. I tried to explain the gallon challenge to her but she wasnt having it. I have to laugh now because its hilarious that she had to pick the 10 min window after I vomited milk to initiate our first kiss. Oh well, you win some you lose some.

I have this thing where I talk to a girl for a bit, get her laughing and such, and then just grab her hand and say "Let's go get some pizza" and start walking off. Has worked every time but once, when the girl pulled away screaming "LET ME GO!"
 
Haha, that was awkward. 
 
I've never asked a girl out, I just take them. :p

Back in early high school at a party i asked my crush to dance with me. She said she was going to dance with this other guy, so i said ''Okay''. Then the next time, i loaded courage and was going to ask again, when a dude i remember i fucking hated, picked her up.

Bad memories, man.

This thread makes me sad.

I think I blocked out all of those bad memories because I can't remember any of the super awkward ones.

I haven't struck out really badly too often, but that is mainly because I have been with the same girl since I was 18 (27 now), and most of the girls before her started off as good friends.

The closest I can get is that I had gone through a really messy break up with my first serious girlfriend, we'd both cheated on each other and generally hated each other's guts.

After about 6 months of being broken up, we ran into each other at a party. At first it was really cold, but as the night went on she started getting really friendly, and my courage was worked up from a few drinks. We started reminiscing about the good times, and before you know it her tongue is down my throat and her hand is down my pants.

Even with all the negativity, I still really loved her (and she was pretty smoking), so my heart was soaring at the chance to get another chance. Then she pulled me up, dragging me off to a bedroom...

...where we promptly met her new bisexual boyfriend, who apparently desperately wanted to have a devil's three way. The both of them had been popping pills all night and decided to hatch the plan to "seduce" me and then discard me afterwards; her because she wanted to get double teamed and to hurt me, and him because apparently he, too, wanted to get double teamed.

With a manly cry of "you people have got to be fucking dreaming," I got out of there extra fast and didn't see her again until I rather awkwardly ran into her in hospital when my grandmother was dying.

ugh too many to mention.

ive got to say the worst ones are times when you really think you were in with a chance.

got shot down by a pretty girl? derp, of course! as if you had a chance anyway but get shot down by the fat and boring type then you start to realize you really are fucked.

OP i hope you are happing making duders remember moments they would really rather forget about.

@Djangosix said:

OP i hope you are happing making duders remember moments they would really rather forget about.

I am.

@jyluth said:

@the_OFFICIAL_jAPanese_teaBAG: I'm definitely missing something here. Perhaps it's because I don't own a hat, so I don't know what it means. :(

The way I see it, if a girl takes your hat and wears it she's likely being playful. If she doesn't know you really well and she does this she's being playful because she's interested in you. If she's interested in you it's time to make a move.

And get your damn hat back.

@Animasta said:

I take offense to this "other" comment :|

I agree we're people too

@sk8nob said:

it's just Awkward City and I'm the mayor.

Lol

I can't share my stories... some aren't good enough to share others are too awkward.

My entire life is an example. I'm terrible at meeting new people, or interacting with them. I've never approached someone. It's either just happened out of chance (co-workers, for example) or just friends turning into relationship. Me hitting on a girl ends up being me sitting quietly and looking at her while I think about all the nice and awesome things I would say. :T

@LooseChange said:

@Undeadpool said:

I once got called a tyrant by a woman after I pointed out that I enjoyed watching people dance from a balcony in a club.

Heh. That made me chuckle.

I started small talk with this girl at a bar then when I proceeded to ask for her number she told me my friend was more cute. Ouch. =/

I laughed it off and had fun with my friends and talked to other girls.

damn that's cold

So there I was, senior year of college with prom fast approaching. I had been flirting with this girl off and on for a while so I thought I'd ask her out, only problem was I had some pretty extensive foot surgery done earlier that year so I was temporarily in a wheelchair. So one lunch break I have my friend tell her that I need to ask her about homework or some bullshit. She comes over and I start to chat with her. Right when I ask her out, my other douchebag friend comes over and says "hey Ben let's go for a ride" and starts to roll me away mid proposal, so I basically have to yell "DO YOU WANT TO GO TO PROM WITH ME?!" at her as I'm being rolled away helplessly, to which she shouted back "NO THANKS."

@SSValis said:

@LooseChange said:

@Undeadpool said:

I once got called a tyrant by a woman after I pointed out that I enjoyed watching people dance from a balcony in a club.

Heh. That made me chuckle.

I started small talk with this girl at a bar then when I proceeded to ask for her number she told me my friend was more cute. Ouch. =/

I laughed it off and had fun with my friends and talked to other girls.

damn that's cold

Yeeeeeouch!

@GlenTennis: And that's the story of how you went to prison for murder.

@Undeadpool said:

@SSValis said:

@LooseChange said:

@Undeadpool said:

I once got called a tyrant by a woman after I pointed out that I enjoyed watching people dance from a balcony in a club.

Heh. That made me chuckle.

I started small talk with this girl at a bar then when I proceeded to ask for her number she told me my friend was more cute. Ouch. =/

I laughed it off and had fun with my friends and talked to other girls.

damn that's cold

Yeeeeeouch!

I love how he brushed it off though. That's about the only thing you can do in that situation.

One time I got a flat tire on a first date. I had to change it at a gas station and it took about a half hour. When we got to the movie theatre her sister was there to pick her up saying I must have been reckless on the road when in reality I hit a pothole with a few nails in it. I was 17, still the worst date I've ever had.

Started up something with this one broad and asked her out towards the end of '11. After a week of waiting date night came along and she told me she couldn't go out cause she wasn't feeling well. Facebook really isn't that bright at keeping things private if it has status updates saying "(insert interests name) was tagged in this photo on (date night)". To which I squinted and said "Hmm". Asked a couple of her buddies what was up and they all said she wasn't sick.

She gets turned down by the guy she was eying about a week later. I get a text saying "Hey. How've you been? Been busy myself so sorry for being a stranger xD"

Kept playing Deus Ex: HR without a fucking care in the world.

I once told this girl she was "making it hard for me", I should've kept my mouth shut and just kept staring at her. I wanted to tell her that her beauty was beyond compare and that for me to keep quiet about this was...

You know the rest. What makes it even worse is that she was super sweet about it and smiled then told me I was sweet, like I was her friends disabled brother or some shit. I'm embarrassed just thinking about it. I need a beer.