What is the most awkward/worst thing you've said to the opposite sex?

[Pythenis]

Set the scene:

I was about 22, a co worker introduces me to a friend of hers she wanted to set me up with (because I was so awesome) ran into each other at a bar.

Coworker - Lisa
Friend - Adina (really cute)
Me - Pythenis
Jim- Friend of Pythenis
Keith- Friend of Pythenis

Lisa- Hey Pythenis (hug)
Pythenis- Hey what's up.
Lisa- Not much, this is my friend Adina (shake hands- Exchange hellos) I was just telling her how her I love her new leather pants, they make her look so slim.
Adina- Shut up Lisa *embarassed*

*Here it comes, with all the best intentions of complimenting and making Adina feel better about herself.*

Pythenis- No, no, I like the leather pants, they do make you look slim.....not concentration camp slim but healthy slim.......

Adina- What...what the F*&K, did you just say not "concentration camp slim", WHAT THE F*&K IS WRONG WITH YOU MY GREAT GRAND MOTHER DIED IN A CONCENTATION CAMP!!! YOUR AN F-ING PIG! SERIOUSLY...( Lisa leads Adina away as she was going balistic)

Pythenis- (turn to my friends and is about to speak) SPLASH!! (Adina throws drink on Pythenis back)

Jim - HAHAHJAHAHJAHAHAHAHAHAHAHAHAH....fff.f..ffmn.....HAHAHAHAHAAH...Ect.

Keith - Wow, just wow........that was awesome.....(manic laughter)

Lisa - I'm so sorry, I'm sorry,...why did you say that....really..Pythenis you such a nice guy why did you say that....I'm sorry she went crazy...

Pythenis - (long island ice tea dripping down the back of my pants, thinking I just want to go home and change right now) How was I supposed to know she was Jewish? I was just trying to say something nice...and I just watched friggin Shindlers List last night.....tell her I did like the pants...

 

[Pink Ranger]

Pythenis = Young Larry David

 

[THE MR. TERRIFIC]

When my girlfriend (now wife) told me she was pregnant (the first time) my response was, "I need a drink!" She was pissed! She still married me and had 2 more of my children so I guess it all worked out.

 

[TheAQU4M4N]

When my girlfriend (now wife) told me she was pregnant (the first time) my response was, "I need a drink!" She was pissed! She still married me and had 2 more of my children so I guess it all worked out.

i think it all depends on how you say it.

 

[Immortalfire]

"You look nice"

I then got hit with a restraining order.

 

[Know One]

Honest to God - the most awkward thing I've said to a girl was...nothing. She was next to me, we were going up the escalator in the metro - we knew each other from work. But...I was like 19. And to this day - when I see a girl to my liking - I go for it.

 

[Sundancer]

As an experiment I started walking around a bar and randomly asking girls if they'd rather be serenaded by a saxophone or a guitar. Surprisingly, they all took the question seriously.

 

[Immortalfire]

I can't do either of those, but I play a mean kazoo.

 

[GoldCrest]

"You look nice"

I then got hit with a restraining order.

Did you copped a feel while you said that?

 

[Spider-Who?]

As an experiment I started walking around a bar and randomly asking girls if they'd rather be serenaded by a saxophone or a guitar. Surprisingly, they all took the question seriously.

As a guitarist, I'm curious to know which instrument won that poll, lol.

 

[socool]

"Hey, ya know, if you came on to me right now, I would TOTALLY not resist."

...I was pretty drunk.

 

[TinkTonks]

As an experiment I started walking around a bar and randomly asking girls if they'd rather be serenaded by a saxophone or a guitar. Surprisingly, they all took the question seriously.

I've always been partial to ukuleles myself.

 

[Shemtov]

How was I supposed to know she was Jewish?

Adina's a Jewish Name.....
But, really, don't make Holocaust jokes. Not even if you think there's no Jews around.
Would you tell a Joke about picking Cotton because there are no African-Americans around?

 

[bullets]

When my girlfriend (now wife) told me she was pregnant (the first time) my response was, "I need a drink!" She was pissed! She still married me and had 2 more of my children so I guess it all worked out.

haha , that's bad and couldn't have been any better than my , "I'm sorry!"

 

[Doctor Evo]

Adina's a Jewish Name.....
But, really, don't make Holocaust jokes. Not even if you think there's no Jews around.
Would you tell a Joke about picking Cotton because there are no African-Americans around?

You mean black people?

 

[knowsbleed]

When my girlfriend (now wife) told me she was pregnant (the first time) my response was, "I need a drink!" She was pissed! She still married me and had 2 more of my children so I guess it all worked out.

haha , that's bad and couldn't have been any better than my , "I'm sorry!"

My reaction was...

"****ING ****! Are you SERIOUS?!"

 

[bullets]

^lol , nice meltdown moment.

 

[Optimus_Prime_]

In protest: "I bet Pepper Potts lets Tony Stark use his iPhone while getting a *******"

 

[Pythenis]

Adina's a Jewish Name.....
But, really, don't make Holocaust jokes. Not even if you think there's no Jews around.
Would you tell a Joke about picking Cotton because there are no African-Americans around?

First off, I was not trying to "joke" about the holocost I was just trying to make her feel better about the pants and I had the holocost scenes fresh on my mind.

To your second point I think everyone makes sure there are no black people around before they tell jokes about picking cotton.....

 

[Spider-Fan83]

No matter how much you own it, "You're cute, like an aardvark", is never going to work out. lol

challenge accepted

edit: challenge failed (face still sore)

 

[Quasimod0]

First off, I was not trying to "joke" about the holocost I was just trying to make her feel better about the pants and I had the holocost scenes fresh on my mind.

To your second point I think everyone makes sure there are no black people around before they tell jokes about picking cotton.....

Who tells jokes about picking cotton?

 

[The Slang]

First off, I was not trying to "joke" about the holocost...

You made a joke involving the holocaust, thereby joking about the holocaust.

To your second point I think everyone makes sure there are no black people around before they tell jokes about picking cotton.....

Some of us don't make racially insensitive jokes regardless of who's around. We're just crazy I guess.

 

[crounsa810]

Welp, got a new one.


"Hi. Hey did you know that male goats piss on their faces to attract female goats? I thought that was really strange. Like if I pissed myself, I don't think any girls would be attracted to me. That would be insane. Nature is funny. Where are you....ok."