Wingmen Reveal The Most Bonkers Plans To Get Two People Together That Actually Worked

Being a wingman or wingwoman or wingPERSON (it's 2019) is a sacred role that only the most worthy can fulfill. It requires thinking outside the box, even stooping to levels you'd never expect. But it's worth it for helping your friends find happiness, and of course, for the stories.

Dalk126 asked wingmen of Reddit: What was the most stupid plan you made to get two people together, that actually worked?

Submissions have been edited for clarity, context, and profanity.

15. Sashay far away.

Pushed buddy into cute girl on dance floor, they got to talking, ended up married, kid, moved to England. Whole plan took like 3 seconds to come up with. Now I just miss my friend.


You literally pushed your friend out of your life... impressive, and a tad depressing.


14. Who needs to play then you've already won?

I invited some friends over to play Monopoly because I like to play Monopoly. It was the first time they met. They realized I was going to play the "all house no hotel" strategy so they strategized to gang up on me.

It's been 10 years and they're still together.

They still won't play monopoly with me.


That's how you know you've played monopoly correctly.


They scored the ultimate monopoly, life with each other.


13. Those were the days.

When I was in like 5th grade I walked up to a girl for my best friend said "hey my friend has a crush on you" started giggling and ran away they "dated" for a year.


I feel like it swings back around to this the older you get. If you're the single friend, you tend to get introduced to the other single friend at backyard bbqs. We all know why they were both invited.


12. Taking the initiative, eh?

I told my bro that I was going to hook him up with someone in a blind date. He agreed.

I knew he had a crush on a girl already, so I went and straight up told her:

"Hey, so I told my best friend (name) I was going to set him up with a blind date, and I already knew he's got a slight thing for you. Would you be interested? I haven't told him I knew he's a little into you so it's a bit of a secret."

"Yeah, I'm in," she replied.

And that's how I hooked them up in a "blind date".

Stupid, because I lied, I didn't actually have any sort of plan at all, I made it up as I went. Two, because I had already spilled the beans about my friend by the time I realized this was a dangerous game. In fairness, he didn't tell me he liked her, I inferred it by myself. So I don't feel like I betrayed any trust there.

Not the craziest story, I know, but it's what I've got.

EDIT: Sorry! Forgot the important bit. Figured it was implied by OPs request. They got together for a while before mutually breaking it off. It was a good break up, they just weren't right for each other.


11. This was a lot of work.

My best friend at the time said that I would make a good couple with one of my friends. Just to tease her, I started joking around that she had liked that same friend.

I very casually asked my friend if he liked her, to which he responded in a very unorganized and panicked manner, telling me that he was interested. I relayed this information over to my best friend, who was equally flustered and panicked. I continued relaying information between the two of them and over the course of 3 weeks, I had peer pressured these two people to get to know each other. They were in a "getting to know each other" phase for a month or two before dating officially.

Unfortunately, they lasted exactly one month and don't talk to each other anymore.


10. The straights are not okay.

On my best friends' first date with the girl I set him up with, they made out a few times. Later that day she called me and said that she doesn't want to see him any more because his breath was absolutely terrible. I told her that he said the same thing about her breath (a total lie) and that she should be nicer and give him another chance. Now they've been together for 11 months.


9. The duty was done, dutifully.

There was a girl I really liked and I thought she liked me too, but my best friend was having a really rough year and always talked about her so I decided to be the bigger man. Standing outside a party wasted on Halloween I convinced them to eat a Fruit by the Foot from either end like Lady and the Tramp. When they got to the middle I yelled kiss and they did. They ended up going on a couple dates but he blew it and now she hates me too.


Very adorable human behavior. 10/10 wingman.


8. This is how you do it.

Writing this to commend my friend for being a wingman for me but I was at a party this year with the express intent of finally talking to the girl I liked back in high school before we all graduated in 2018.

Kept holding off on approaching her and striking up a conversation so my friend went up to her and pretty much said "hey my friend basically hates everyone but he really likes you and he really wants to talk to you but hes too much of a bitch to approach you, could you please talk to him and just see how things go."

So she came up to me and we started talking and things went well.

We've now been dating for a month and things have been great.


7. Wingmaning by proxy.

I've been looking for a thread that I could post this on. I was a stranger's wingman. Got the job done for him and I don't even know his name.

I have a female friend who messaged me that the most embarrassing thing had happened to her. She has an "open house." Any of her friends may walk in at any time if they need anything. One of her friends walked in while she was masturbating. Not just masturbating a little bit, but full nude, on her knees, riding a large dildo. She was mortified!

But also turned on. She had been going through a months long dry spell, and the guy was very attractive. He came in because he needed somewhere to stay for the weekend. I think they were fumigating his house? I'm not sure, it's been years.

So there she is, hours later, kids are in bed and she's watching a movie with this guy, when she messages me again. She wants to f*ck him, but he hasn't made a move. She's from a family where the woman never makes the first move, she hasn't even considered the possibility. I not only talk her into it, but I talk her through it. It takes an hour, most of which was building up her confidence enough to just do it. She said it was great sex. She thanked me for helping her out.

The next day I tell a different friend that I had done this. He looks thoughtful for a minute, and he says "Ya know, I wonder how many times a girl wanted to f*ck me but no one was there to talk me through it."


6. Extreme but effective.

I pretended to be a gay boyfriend to my "bi" friend so he could get closer to her. We "broke up" and they got together.




Yeah, he was my homie.


5. Getting schwifty.

To preface this, I'm a fairly big guy, gentle giant type, not so gentle when drunk. I was drinking with my gf at the time and our mutual friend at a club. Mutual Friend spotted a guy dancing with his mates and told me she thought he was cute. I was fairly inebriated and thought it would be a great idea to dance into his friend circle, dance/hipthrust him out of said circle, and forcibly dance him into the arms of Mutual Friend.

They dated for 4 years after that so it was a success but probably wouldn't recommend that tactic.


I tried to picture that in my head, and it's hilarious. You basicslly became a human bulldozer.


4. What a bro.

Wingman recipient here.

My best buddy knew I wanted this girl but I didn't know how to pull the trigger. This girl was gorgeous. He was outgoing and good friends with this girl. He also knew she was into me. The three of us were wasted at a party at her house. He told us to come upstairs to her room. In her room he said we were gonna play a game and all strip down to our underwear.

By the time she and I were down to our undies, he was fully clothed still, gave me a butt smack and closed the door as he left the room.....

closed the deal, twice.....

Never forgot it.


Lol. His plan was simply "get them naked."


3. She's a mess.

My college roommate was heavily flirting with this one guy from our dorm. He hadn't officially asked her out, but it was pretty clear he wanted to. And that Roommate had a huuuuge crush on him.

Problem was, there was another guy who'd been hitting on her. He was creepy (I don't mean that in the "ew, he wasn't hot" way- he'd get overly sexual and physically aggressive at frat parties to the point where multiple frats banned him). Roommate didn't like him, but kept talking to him because she had weird emotional issues about saying "no" to people and blowing them off.

So she wasn't making it clear which guy she liked, they were kinda fighting over her, and the whole thing came to a head right before they were gonna leave for a frat party. Creeper demanded she pick who she was "going" to the party with.

I half shouted, "Well she HAS to pick [Roommate's Crush.] She owes him for teaching her pool today."

Roommate's Crush jumped on that, claimed his "right" to take Roommate to the party, and they were officially dating by the end of the night.


How does it end?


Badly. But it was probably Roommate's fault. She was a neurotic mess and CRAZY high-maintenance.

Like, over Valentine's Day, our dorm had this thing where they put hearts on our doors so everybody could anonymously write nice things about one another. She counted the number of nice things on everybody's heart, averaged them, and had a meltdown when she got one less compliment than the floor average. I came back from class and found her curled up in a ball, SOBBING, in her closet. Took me two hours to calm her down, and I only managed it by convincing her that her friends were procrastinators and hadn't gotten around to doing the hearts yet. (That night, I snuck out of the room at 2 am with a bunch of different pens and wrote random nice things on her heart, and several other people's because if I just wrote on her's she'd have figured out it was me and had another meltdown about being "pitied.")

I can't imagine what dating that mess was like.


2. Sometimes roommates know best.

So I'm the one who got coupled up, but here it is. For about 4 months my roommate would invite this girl over to watch trash movies together, once a week. I had no intention with getting together with her cus she is 2 years older and obviously out of my league. It worked because he didn't tell me that this was his plan, because otherwise I would definitely have messed it up. Once we started dating he came up to me and spilled the beans, and said "I was close to losing all hope with you, finally."


1. Be who you are, and accept nothing less.

Oh I actually have one! I have a friend with a medical condition called Alopecia, which makes the person lose all the hair on their body. She suffered from depression and really low self esteem because of this, and always wore a wig.

So we were at a party 10 years ago, and she saw this guy that she found very interesting. I told her to go talk to him, but she didn't dare to. So I asked her to come with me to the bathroom, and when we passed the guy I gave her a small push so she kinda fell into him. Well, they spent the rest of the night talking and started dating.

Then one day about two weeks later she called me crying saying she really liked this guy, but she was so afraid of him finding out she didn't have any hair and wore a wig. I told her to go tell him, and if he didn't accept that part of her, he didn't deserve the rest of her.

She called me that evening saying she told him and that they were now boyfriend and girlfriend. Today, ten years later they are happily married and expecting their second baby :')


Fame always come with a price!

Fame is a tricky, tricky mistress. It can be intoxicating and make you crave it; until it ruins you or until it does you right. And thanks to cable television and the internet anyone can be famous for literally anything and nothing all at once. Who knew being a "Meme" could garner you a fan club? What does one do with that sort of fame.

Redditor u/AnswersOddQuestions wanted to hear from those who are part of Meme fame by asking.... People who have had their pictures end up as memes. How has it affected your life?

I wanna be Memed!

Keep reading... Show less