What are your funny wing man stories?

I was the wingman.
We were at a joke "America" party on September 11th, held by a friend's sister and her roommates. Red, white and blue jello shots- that whole thing. They did well planning.

My brain is shutting down at the end of the night because I had been pulled into a flip cup game while already drunk - thinking I was replacing someone and had a beer ready. What really ended up happening was I had to chug over half a cup of Bacardi because I was just drunk enough to be that fucking stupid. Totally won the flip cup game for the team, though. Not worth it.

My best friend has had a huge crush on the sister for the last half a year, but is currently stuck chatting to some cute, artsy/hipster blonde since the sister is proving hard to get at for him. My drunk ass approves of this new opportunity for love.

A flag is hanging on the wall, and people pass us a sharpie in order to sign the flag to commemorate all who attended or something. Next thing we know, the blonde is drawing a friggen Swastika on a flag like she never left middle school.

My drunk ass gives a look of disapproval, and concocts a game plan.

Drunk: "Where's<friend's sister>?" Friend: "I don't know. Why?"
Drunk: "Shehlikesmih." (She likes me.) "Dude, you're not going to hit on her, are you?"
Drunk: "Nahhh."
"What do you mean she likes you, then? "
Drunk: "Stwanna dater?" (Still want to date her?) "Uh, yeah. The fuck are you talking about, though? Dude-..."
Drunk: "Gotcha." (Nods and turns.)
"Wait wait. Am I going to be taking care of your drunk ass all night right now?"
Pauses. Turns back. Drunkenly Nods. "Prolly" (Pretty much) Turns again

Long story short: all throughout many hilarious half-conscious conversations and female roommates gauging my awareness by asking how much if I like tits (fuck yes, drunk me likes tits. What kind of question is that?) and seeing if I'd remember them flashing me the next morning or something weird (Easiest fucking challenge in my drunken life), already-fated-to-be-passout-drunk me takes full advantage of the bathroom and my friend's diligence with making me chug water for the night.
And the sister takes good note of this and appreciates him helping me since I have known her for many years.

Next morning, I wake up completely fine and to my friend's look of disapproval visibly conveying an expression of You fucker straight at me and my shit eating grin.

He tells me he had to stop hitting on Ms. Aryan Dream in order to force water down my throat all morning (He has this awesome habit of going overboard with water. I mean, hey, no hangover so I'm not complaining.)

I simply state, with a sublime nonchalance: "You're welcome."

Ahh... if only I could frame a picture of the next moment on my fridge - never to be replaced by anything, even my own children's drawings unless they should prove talented enough to study and reproduce that exact same scene in their childish hand. The next moment is one of incredulity. His mouth opens. He wants to say something. He begins to form words- annnnd then in walks the sister, and the look of You fucker goes even further into a kind of look meaning If I could murder you without losing you I'd do that right now... more than once which you only get to pull off a couple of times in your life.

It was perfect.

The sister sees my attempts to stifle my shit eating grin, but doesn't waste time on it yet: "I got <friend> for you like you said."
Sober: "Thanks. I owe you one. And: sorry. I hope I didn't throw up on anything."
"No! It's fine! Are you alright now? And <Friend> made sure of all that. He was in here all night making sure you drank enough water and didn't pass out."
"Yeah! I'm fine! You should really get one of him (nods head in direction of friend). Really works like a charm."

The crook of her mouth turns upward in a look of approval when I give the recommendation and thanks him for keeping her stuff safe from projectile vomit.
My friend is too focused on trying to penetrate my still totally blasé face and giving me looks in order to notice the karma points which I have brought his way in exchange for the sanctity of my liver, though. He's quite prideful about being able to pick up chicks on his own usually. He doesn't realize I'm accomplishing more in 6 hours than he's accomplished in 6 months with this girl.

She throws out a friendly, "I don't know what I would've told my brother [my other best friend] if something had happened to you!" and then pats my friend's arm, and flashes him smile.
My friend tries to remain steadfast in his chastisement, and to grunt his disapproval toward me as I continue to enjoy feigning being unphased. But now that his existence has been acknowledged, the throes of passion are already working their magic upon his great romantic heart and softening his anger, unbeknownst to him. He says in a begrudging, familial tone: "Yeah.. well... someone had to watch this asshole."

I hold out my water cup as he can take it from me now; ensuring to further indicate how I'm done with it after puking all morning.
"Ohhhh noooo. Go fuck yourself." comes his best attempt to pretend that wasn't witty.

The sister and I both laugh.
He's trying his best not to smile, but he's already trying to enjoy his time with her and when he says "You think that's funny, huh?" his teeth are starting to flash as a sarcastic grin appears as he shakes his head.

"It was, yeah" is the sister's jovial reply.
He looks up at her to see that she's still smiling. Only now she's looking at him as well.

My friend clearly tells a baldfaced fucking lie: "I'm totally not helping his ass next time."

Except he isn't looking back at me any longer.

/r/AskMen Thread