People Share Their Absolute Best AND Worst Wingman Stories.

A wingman is essential in providing emotional support as you muster up the courage to approach a potential partner. Sometimes this is for the best. And sometimes...well, not so much. Here, people share their best AND worst wingman stories.

1/22. I was flirting with this girl in a bar - we'll call her Jill, but her friend Beth was totally killing the mood, being negative and generally bringing the table down.

At one point, I turned to my buddy sitting next to me and said, "I wish we could get Beth to leave, so I'd have a shot with Jill." My buddy shrugs his shoulders, picks up his beer and blatantly pours it all over Beth.

Not spills, picks it up and pours it down her chest and into her lap. The entire table sits there stunned for a second, then Jill looks at me and says, "You were just talking to him, did you ask him to do that?"

Before I can reply, my friend just quips, "Yup, his idea. Well, I need another beer, anyone else?" before getting up and heading to the bar.

Needless to say, things didn't work out with Jill.


2/22. I was trying to boost my friend's confidence to get him to talk to a girl. Gave him the age old advice of being confident and a slight jerk at the same time. He proceeded to walk up to a beautiful girl and ask her, "What's up, ugly face?" Needless to say, he didn't have much success that night.


3/22. I promised my best friend I would find him a girlfriend.

I ended up being that girlfriend. Laziest wingwoman?


4/22. My wingman blew it for me once. Freshman year of college, we went to a party in our dorm (the floor below). I had a crush on the girl who was running the party and wanted to hook up with. Her clingy best friend was there and my friend was supposed to keep her occupied (just by talking to her or whatever) while I flirted with the roommate.

It was working out great and by the end of the night it was just me, the girl I liked, my roommate, and the clingy girl left at the party. Clingy girl left, my roommate says to her,"Okay bye," and proceeds to stay in the room with us.

Even after 2 hours of subtle hits to him he stayed in the room. Eventually it hit 3AM and she could sense that he wasn't going to leave and heads to bed.

We both leave.


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5/22. I was working for a theme park as a show host, as well as being part of their technical team. This theme park, like many other smaller parks, outsources its main stage shows to one of a number of companies that specialize in that. These companies then hire people from across the country and set them up in an apartment.

The regular employees had, of course, a welcome party for the contractors. We're all in our twenties and performers, so we're drinking. My friend Kyle, who was my lead tech, comes up to me during the party and says, "Man, I really like Johnny, but Rob won't leave us alone."

This was a man I had trained and I had spent a year seeing every damn day. So I distracted Rob with drinks and accidentally led him on all night.

The next morning I woke up on the floor with Rob spooning me.

We got in the car to leave, and I turned to Kyle and said, "I brought my wingman A-game last night, you owe me.


6/22. My buddy was really into this girl on a party, so I started talking to her (he is really shy), and got her 3 tequilas to make it easier..

Ten minutes later and she pukes all over my friend.


7/22. In college my roommate befriended a little cutie from Minnesota in his biology class. She would come to our dorm (with an open floor plan- no privacy) to study. It was obvious my roommate wanted to get wit her. We commenced to come up with a plan to do so. He and I decided we'd invite her and others to our dorm to drink, and see if he could manage to find his way back to her dorm after things winded down.

Things go well. We all drink a lot. Our neighbors leave our dorm, leaving only my roommate, the girl, and myself. I was very drunk- I quickly passed out.

My roommate decided to roll the dice and attempt to have sex with this girl a mere five feet away from me. I woke up at maybe 3am to weird noises. Though shaken, I played it cool and feigned sleep until he could wrap things up.

Im proud I didnt alert them of my consciousness.


8/22. This was at an adult beverage festival. I was taking a photo of two friends wearing ridiculous hats when two girls photobomb us. The two were cute, slightly inebriated and flirting heavily so clearly the right thing to do was to approach them, however I honestly wasn't feeling it.

Our other friends left us and being the stand-up guy I am, I continue conversing with one of them while my friend is clearly hitting it off with the other. This goes on for what felt like forever, but finally we broke away with the girls promising to find us later.

So I ask my friend if he got her number, he replied that he hadn't bothered and asked the same back. At this point we had a man-to-man moment and we both realized we were being the wingman for the other but neither of us were interested.

That's friendship.


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9/22. I was in a club with my friends and I started dancing with one super attractive girl. Her annoying friend was trying to get her away from me. Enter my best friend. He slowly got the annoying girl away long enough for me to dance with the hot girl and get her number and so on.

I could see my friend trying to get my attention and trying to shout something to me but I couldn't hear. He kept on trying to shout when suddenly the music stopped as he was still shouting, "WHY DO I ALWAYS GET THE ANNOYING ONE?!?!?!


10/22. I'm gay, and my friend is straight. I took him to a gay bar to hit on the straight girls that came there just "to dance."

Anyway, we approach this group of girls and I put on the I love your shoes and Here's my straight friend who came out to support me but now wants to dance with someone routine.

Instead of being flirtatious and jovial he starts going on and on about his mother...needless to say, they promptly walked away.

Being a wingman is tough work sometimes.


11/22. Friend told me about a smokin' hot tan girl he wanted me to wingman with him. I walk over and introduce myself and say "Hey my name's _____. You must be the tan girl!"

I swear I swatted at the words as they floated out of my mouth. There was no taking them back.


12/22. I was friends with this really great guy, and he'd been single for a while. He was fairly shy and quiet, so I decided to help him out.

One night, we went to Applebee's for dinner, and I left his number for the waitress. But it was him, my 2 kids, and myself; I realized after we left what it probably looked like to the waitress. We both laughed, though.

I tried to set him up with every single female friend I had. They'd meet him, hang out with him, and then tell me, "He's great, but it's not going to go anywhere." I figured I had stupid friends.

Well, one day, one of them breaks it down for me. The reason no one wanted to go for him is that, to him, they'd always be second to me.

I figured my friends were joking. Until one night, one thing led to another and three months later, we moved in together, and a year later we got married.


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13/22. I had been flirting with this waitress for a while and went to her restaurant one night with a friend after hitting the bar. She and I are chatting when she mentions something about her recent ex. I love my friend but he's a bit clueless and he says, loudly, "[My name], she's saying she's single!" I was like, "Thanks bro..."

We left shortly after. I told him what he said the next day and he was embarrassed and apologetic.


14/22. My mate was having a party at his place, and had invited a girl he likes as well as some university friends. Unfortunately that girl couldn't make it but she told him to come over for movies at hers the next night.

I knew another girl coming to the party had a serious interest in my friend and he had slept with her several times before. This other girl is out of this world hot.

Skip to the end of the night and I had seen the girl flirting with him and deciding to do the friend thing and not the wingman route, I tried to keep her away. Once people started heading off to bed, I went and claimed his bed as my own, assuming he would just collapse into it knowing he couldn't bring her in since I was already there.

Skip to the next morning, I wake up to me and him next to each other and then the amazing figure of beauty on his other side spooning his body. I knew they would sleep together if I left before everyone else woke up, so I laid there staring at the roof until the rest of the house started moving and it was safe to leave them alone.


15/22. We were out partying in another city, a group of friends having some short vacation.

And there she stood, in a group of girls there was this cute brunette. And so the game of exchanging looks began, no one daring to do the first step.

Trying to get courage I tell to a friend.

"Hey, that girl over there and I are ogling each other"

And so came his answer from the bottom of his hearth."Do you really believe she looks at you?"

Disdain in his voice. I was less than a worm. Confidence was so crushed that you couldn't watch the remains without setting them aloft with just your breath.

I haven't forgotten, forgiven, or gotten over this yet. More than ten years and it still stings. This deep wound hurt our friendship until it ended.


16/22. One of my best friends is super outgoing and better looking than I am, and was unknowingly one of the worst wingmen I've ever had. I remember one night there were at least 5 different times where I would be talking to a girl, he would join the convo, and 10 minutes later he was grinding with said girl on the dance floor.

The most frustrating thing was that he has a girlfriend that he's very committed to so he wasn't even looking to hook up. I called him out on it after that night and ever since then he's been the best wingman I could ask for.


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17/22. I was at the bars with a couple of my friends. One of my friends says he is gonna find me a "nice girl." Well shortly after that he succeeds, he finds a couple of cute girls and introduces them to me. We are all talking for a little while, one of the girls asks where we are from. We are all from a town about 200 miles away from where we currently are. Then they ask what brings us to our current location...

My friend says, "It's his bachelor party!" and points at me, when it was in fact, not my bachelor party. My jaw drops and I just stare at him. Shortly after that, the girls bailed.


18/22. Came home from work and my roommate was at the computer helping some hot girl with her homework. I knew who she was, and knew she was single, and had no idea how he got her home, but good for him.

Unfortunately, the guy was a slob and his stuff was laying around everywhere. But I didn't miss a beat.

"Hey man, I didn't know you'd be bringing anyone over, or I would have cleaned up my mess."

He comes back with, "What are you talking about?"

"All this stuff is here, I wouldn't want her to think this is your fault."

"It is my fault... this is all my stuff. What are you talking about?"

I looked her right in the eye and said... "Well, I tried. You saw it." Turned around and left.

I could hear her laughing on my way out the door.


19/22. This one night I was high and drunk. My former roommate's brother was this desperate freshman kid who kept asking me to hook him up with a girl. I was senior by then. I felt bad for the kid because I was inebriated and couldn't talk to any girl for him. Plus I didn't know that many people at the place. So I let him hit on my girlfriend.

She obviously turned him down. I pretended to not be aware of his moves. He didn't know that she was my girlfriend. I patted his back later and my girlfriend explained to me how this young kid had the worst pick-up moves ever. Apparently, he was came off as really creepy.


20/22. My friend and I got dragged by a few girls from class to this country bar/line dancing club. I'm hanging out with them in the general vicinity of the dance floor and a girl taps me on the shoulder and asks if I want to dance. I'm not single so I tell her I'm taken and she moves on.

Not 10 minutes later another girl taps me on the shoulder and asks the same thing. I assume I stand out because I'm one of the only guys there not wearing a John Deere hat and a plaid shirt tucked into my jeans. I tell her I'm taken and she leaves me alone. My buddy with me, who was also bored as hell, was single at the time so I decide to try and send someone his way if any other girls want to dance with me.

Sure enough another girl taps me on the shoulder and I begin the sentence, "Hey, I'm taken, but you should talk to my friend over here." Unfortunately my friend only hears me say, "I'm taken...", sees me point to him, and he gets the wrong idea. Before I finish the sentence he immediately puts his arm around me and says, "Oh, I'm sorry honey. He's with me."

The girl just stares blankly at us for a few seconds and goes, "Good for you guys, totally buying it. My only regret is that we doubled over laughing before the girl even turned around.


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21/22. I was talking to a girl at a party. Now, this place was on the 18th floor of a high-rise and we were out on the balcony admiring the view. My friend comes up and tells her, "[My name] told me earlier that he could pick you up and throw you off the balcony." I did no such thing. It did not go well.


22/22. I started college in a new town and didn't know anyone. I met a guy and we bonded, became pretty good friends in a short amount of time.

One of the girls here, she's been friends with him for a couple of years. Now, we're out in town and having a good time, he tells me he's had a slight crush on her since they met. I, in a strangely confident tone, proclaims that I will wingman him out of the friend zone.

We enter the most popular bar and what do ya know, she's there. He, along with more of our friends, get a table and chill, while I go over to her to talk, with the intention to change her thoughts about my friend. I'm sitting there, just talking, and you probably get where the story's going. We order more and more drinks, and the conversation is really flowing. I also notice how incredibly attracted I find myself to this girl.

I couldn't help it.

I kissed her. And before you know it, we're sitting there, making out like there's no tomorrow. We part lips and I suddenly realize what I just did. I look over to my friends' table, and saw my worst fear. My friend, looking absolutely heartbroken. He stormed out of the bar before the girl could notice him.

Now I had a choice. I could either run after him and try to mend the wound, or I could most probably get laid with this girl. It took me about a second to consider the two choices before I ran after him.

He was sobbing at the street corner, and we had a nice, long talk. Mostly about how I'm a jerk. But then he surprised me. He thanked me. Because he was now over her, somewhat. When he saw us doing the tongue-tango, he wasn't that hurt because she kissed another dude. He was hurt because I, who he thought was a friend, betrayed his trust.

I apologized profusely, and he forgave me. We went back in, and he told me that if I wanted to, I could have her, though I could tell he didn't mean it.

So I paid for two beers, gave one to him, and found a different girl for him. This time, I did my job right, and my boy went home with this new girl.



Breaking up is hard to do.

And when you get the law involved, it's even worse. But sometimes people don't need the law's help to make things overcomplicated, they just have a grand ole time making that happen themselves.

People on the front lines of human cruelty include divorce lawyers. These are their stories.

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