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.

50. It's All For The Best


Dated a girl that liked me. We eventually grew apart but just before we broke up i recommended she date my friend who i knew liked her after i mentioned she doesn't like me anymore as a joke. She actually asked him out to get to know him, and they've been dating for a while now


49. Makin' Atmosphere

Over the summer, I was at a bar with a group of my friends. There was a man there that my friend had been eyeing all summer, but she was too scared to make a move. Very drunk me promised her that if she could just start a conversation, I'd take care of the rest.

So once they started talking... I convinced every single other person at the bar to go to the outside section instead. I talked to more strangers that night than I ever had before, convincing all of them to leave the bar for a while. I must have talked 20 or 25 people total into leaving the bar to go outside.

Bonus: once they were all outside, I hung out around the door so people wouldn't be tempted to wander back inside. If I remember right, everyone had a pretty good sense of humor about the whole thing, and it was successful - he kissed her!


48. Conflicted Feelings

I tried messing with my younger cousin: took her Ipad then wrote something ambigious like "I always wanted to tell you that..." to the first boy I saw as she was embarassed and tried to steal it back.

Apparently it triggered confession from him and she was mad at me for doing it while happily hopping around. I guess worth it.


47. Stage 4 Clinging

My friend wanted to get together with her crush, he had a crush on her. Her crush and I had a huge conversation in roblox about it and they became more than friends. He became really clingy and they broke up.


46. A Time Before Gay

Wingwoman, not wingman, but still.

Guy I am friends with wants to date a girl I am also friends with. One time they happened to be standing behind one another (facing away from each other). I ran in, tapped their shoulders, so it seemed like they tapped each other's shoulder, and skirted out of there. They ended up dating for 7 years before the girl came out as lesbian. Good times


45. A Burger Of A Time

Not exactly a wingman but I was asked by a friend if he should ask a girl out and asked me how, of all people he asked me... Well any way I sort of knew the girl from college and happened to remember how she loves a good quality burger so I suggested asking if she wanted to go for a nice burger and it worked. They have been together for maybe 7 months or so now.


44. Even When You Try Not Ruining The Moment

My best friend liked this guy. So I started playing wingman for them. He texted me saying we should get a group to hang out. He came up with the whole plan but I had to take credit. I then asked my best friend if she would be up for a mall trip with the group. She told me good luck getting the guy she liked to go (little did she know he came up with the plan) at the mall we were walking around. He went up to ask her out and I decided to run away to not ruin the moment. I ended up knocking down an entire display shelf at the store and ruined the moment. But hey in the end they are still together!


43. Happily Ever After

I had a single colleague, my girlfriend had a single friend (female), we dropped them in a group msn chat and me and my gf left immediately.

They are together for 10 years and have two kids.


42. Years Down The Line

My GF (now fiance) and I had a special relationship with her best friend. My best friend tells me he's had a crush on her best friend, and was trying to figure out how to ask her to prom. After making sure he was cool with our 'history', I told him just to ask her.

He then proceeds to ask her what she would like for a promposal, then sneakily does those exact things while she isn't looking. Homemade cards, messing with slides on the teacher's presentations, and a few others. She of course said yes, and he just asked me about a week ago to be their best man.


41. Amicable Divorce

In the midst of divorce, I was talking with the soon to be ex about my best friend. Ended up giving him her number, and gave her his, and now they've been dating for 7 months and things are serious.

I miss seeing my best friend all the time, but at least I know if things continue to get serious my kids will have an awesome step mom.


40. Secondhand Serenade


This is the story about how my friend wingman'd me once. I was in a foreign country on my birthday and decided to go to a bar with my friend and some people from the hostel. The bartender there was pretty cute and one of the guys from our group successfully convinced him that, in our strange made-up country, it was custom to kiss the birthday person. I got a kiss on each cheek from the bartender and a serenade later thanks to my friend (no idea how she did that, though).


39. The Same Goals

Wingwomen here, my friend wanted to get together with one of my friends and didn't know how to, so I told him to just go ask her.

The stupid part was that my friend he wanted to ask out was about to ask him out.

38. Yikkity Yakkity

So kinda the opposite, because my friends were being anti-wingmen for me, but it's still a good story.

I was very involved in my youth group and so I went to this big international convention. This girl from across the country who I was originally supposed to get with there dumped me (to be fair I was being really awkward). Anyway, I became super depressed (at the time seeing her was the one thing I had going for me because other stuff had also been going on, although in hindsight she wasn't nearly as amazing as I made her out to be at the time).

Anyway, at this time Yik Yak was still a thing, and now you could meet and dm people through Yik Yak because they added handles. I decided to try this and met a girl. She sent a picture over Yik Yak to show me what she looked like. The picture didn't make her look as unattractive as she really was, and my standards had significantly dropped, so I was down to meet her up the last night of the convention. We tried to meet up a couple times but couldn't find each other, but she was still trying.

Anyway, I kinda came to my senses and realized I didn't wanna get with this girl, so then the following happened:

First, this girl I was friends with who used to have a crush on me prior to the time of the convention (I never liked her back like that) was kinda friendly with this girl who was trying to get with me, and when my friend heard her mention me by name, she told our mutual friend who also knew this girl trying to get with me. He just stalled her, and then after some time said "no!" and jokingly tackled her (he was a small guy and it wasn't like a real violent assault). The thing is this mutual friend was someone who I previously had some issues with, and after I found out about what he did I came to appreciate him more.

Second, one of my best friends, completely unbeknownst to me, also decided to look for someone on Yik Yak and met the same girl a bit later (I guess after she started to give up on me). Except here's the thing: my friend wasn't at the convention. He was at home (he lives in my home town). He just set his herd where the convention was so he could follow the shenanigans, and he has a hacked version of snapchat where he can use geofilters from wherever, so he decided to pretend he was there to screw around with her (my friend's kind of a jerk btw). Anyway, it was a nice coincidence because it got her off my tail.

Fast forward some time and we find out we're doing the same summer program (and it was a small program so we'd be seeing each other a lot). I felt bad and wanted to apologize to her about the whole situation at some point on the program. While on the program, I was talking to this other girl who I made friends with and I told her the story about what happened. She told me that she talked to the girl who was trying to get with me prior to the program.

At this point, she had set off a bunch of red flags during the program and every else grew to dislike her. I still kinda felt bad for accidentally leading her on and dealing with all that other stuff, but I am still glad that I really dodged a bullet there.


37. Abroad Is The Key To Your Heart

Four years ago my best friend was interning abroad and was often talking about not having a girlfriend. Once we were on the phone and I heard his roommate (a girl) asking him if he wanted to join her at the bar with another (girl) friend of hers. My best friend had already had pizza and beer and just wanted to stay home. I told him "If you're not going, I'm never talking to you anymore !", both of us obviously aware that that was an empty threat. He still went, met his roommate's friend and they dated for 3 months !

Then, two years ago, exactly the same situation. Internship abroad, no-girlfriend talk. I convinced him to install OkCupid and he met this girl once. He felt she was not "that" cute and didn't want to see her again. She asked him out for a second date, wanting to meet at the bar to dance. Same situation as before : already ate, already had a beer and I was on the phone with him when she asked. He didn't want to go but I spammed him with videos of the kind of dance they do in her country (bachata) and told him the exact same thing "If you're not going, I'm never talking to you anymore !". He reluctantly went, loved it and by the third date he was in love. They've been dating for the past two years now and just got engaged. They'll soon get married and I'm so proud and happy about it :')


36. Shoesies

It didn't work long term, but I took my buddies shoe, ran and gave it to the girl he had a crush on. I just ran up to her and said "hey can you hold this for me" She looked confused and said okay. He had to go and talk to her to get his shoe back and she was so confused as to why she had his shoes that it gave them a conversation starter which then led to them going on a few dates.


35. International Relations

I once managed it from the other side of the globe, which I was impressed by.

I had two friends. One from Girl Scout Camp, and the other from college, but we bonded over working summers at Girl Scout camps, and being queer.

So my college friend mentioned that she was doing graduate work in Dunedin. She told me in PMs that she was having a hard time meeting queer women in this new place.

It was the very town my camp friend lived in (I knew because I'd visited). I also knew she had a thing for American girls (I walked in on her making out with the lifeguard at camp and didn't out her, and she was dating a different American student when I visited. I had a huge crush on her, but never made a move because I never saw her single). I didn't know the current relationship status of the Kiwi friend, so I just told my college friend that I knew someone who could probably show her around. I then asked my Kiwi friend if she'd help my college friend figure out where to meet women. When they were both keen on the idea, I gave them the others contact info.

A month later I saw that they were in a relationship. I thought I did well from so far away.


34. ARK

I was the wingman for my older sister when I was in 8th grade. She had a crush on some guy in high school but was too shy to talk to. I asked her what his name was and she said his name was "bob". My sister overheard him talk about Ark: Survival Evolved on PS4, so I went to the nearest GameStop and bought Ark: Survival Evolved on my PS4. One day I shadowed her at her high school for a day and talked to him because he was 2 seats in front of my sister in their class. I asked what console he plays on, and he said PS4. I said I do to and asked for his username so I can friend him later.

The day comes and I set a little server for just me, my sister (we have to share) and him. Before I told him the password for the private server, I tweaked a bunch of things to be easier for my sister, who never played a game so hard. I turned Dinosaur Damage to 10%, and multiplied XP boost and gave my sister a tutorial.

He comes online and I give him the password and hand the controller to my sister. They had a great time and I heard from her that they talk a lot more now and are considering going on a date soon


33. Nerds Are In Now

Oof, Craigslist.

This was maybe 10 years ago. A good friend of mine was having trouble in love. Typical nerd, had a nice place, job etc. but kept meeting girls that liked him up until they saw his shelves of video games, manga etc.

Me and another friend made a post for him on Craigslist without his knowledge. The post was honest. It explained the situation, listed his qualities both good and bad and had a few pictures.

We didn't pose AS him, we were honest about that too.

Got maybe 5 actual responses, we vetted that down to two that wanted to go on a date and then told him everything. He took it well and went on the dates. I was best man at him and girl #2's wedding, and they are still happily married.

They asked me not to mention Craigslist in my BM speech, it already had a fairly bad stigma and I just had no idea


32. Drugs Are Always A Good Negation

I mentioned this once, but I was an anti wing man.

My buddy wanted to go home with this girl he just met that was into him too, but he had a girlfriend and felt he should be faithful ( he should've broke up with her, it was complicated). He mentions I'm part of the package and I caught on with what he was doing and acknowledged it. She agreed.

Didn't expect that. I then say I'm not feeling it tonight. Buddy's is like oh no...I guess the plans are off. She pulls me over and shows me her friends, tells me to pick 2. That's just not me, but I stare for a bit and finally tell her, I'm still not feeling it. I then go into this semi depressed, its okay guys, you can go back together, I'll be okay. My friend is doing a no, I can't do that to my ______ bear. He's making a pouty face. All of this goes on for a bit.

She's getting frustrated, goes to the bathroom with her friends. My buddy refuses to ghost her, but wants an excuse to not go home with her. They come back and sit down. My time to shine. I get between them, put my arms on both of their shoulders. I ask, " do you ladies want to smoke some." They freak out and run off. Problem solved.
Ridiculous plan worked technically in both directions.


31. Eternal Gratitude

Andrew if you ever read this, Still can't thank you enough for this one.

I am the person that got the girl, and Andrew was the "wing" man for this. I had a big crush on a classmate back in freshman year, I kept hinting at her and talking to her about wanting to date her but she always refused me. Being down in the dumps, our mutual friend (wingman) kept pushing her away because she had a crush on him. So he told her why aren't you dating so and so? He has been working on dating you for over half a year now. He really wants to date you, you know that. She is Vietnamese and the whole reason why she wasn't dating me, was because of the whole date within race mindset from her parents. Strict Parents. She was afraid of her parents, and our friend just told her love has no boundaries or reason to be held back. Next day when I got her a valentines candy gram at school, she confessed to me and we dated for two years.

Thank you again Andrew if you read this.

[username deleted]

30. Not So Eternal Gratitude


I don't think this counts but here we go.

I got told by my ex that his best friend liked my best friend. I told the best friend as a joke and she looked dead serious at me and said "really? That's amazing!"

So that's how I ended up having to spend a year hanging with my emotionally manipulative ex while our vest friends went out and did nothing but hug and talk.

We were 16.


29. Creation

Me and two friends were supposed to go to the gym, but I got lazy and decided to take them to a pool my ex worked at to visit her, then i took on him on the slides and i knew the girl working the slides, I thought id be funny and slide down so that he would have to wait up there and talk to her... I waited 15 minutes at the bottom of the slide only to walk back up to them laughing and talking. They have been together for almost a year now and they are beyond happy. Fun Fact Im known as Wingman god between all my friends.


28. I Just Wanted A Coke....

He was to afraid to ask her so I wrote a letter without him knowing and I tell her to go to the vending machine and I tell my bro to go there and I would catch up 2 minutes later they are making out.


27. Paid

Was chilling outside the club with the girl I had a crush on at that time. We were just talking and complaining about the bad music and stuff, when suddenly a random drunk guy came up to us and blurted "Now kiss her already". Worked out, we dated for a while.

Years later I found out, that my best friend actually 'hired' this dude for a beer to get us together.


26. How To Set Them Up

I wanted two of my friends to meet, so when friend A was moving I told her my buddy has a truck and we we would come help. Then I told her I couldn't make it for some reason but my friend was still willing to help. He helped her move that day and now they have been together for 10 years and married for 6.


25. Lazy Success

My roommate was planning on going to this big casino night charity thing the rec-league we played in was hosting. I couldn't go and he was texting me saying he was thinking of bailing rather than go alone. I texted a lady friend of mine and was like "aren't you going to this? Can my roommate tag along with you so he's not by himself?" I then texted them each other's phone numbers. They hooked up that night and dated for a couple months. I wing manned both of them without even leaving my couch. It was probably my finest wing man moment.


24. Makin' Eyes

I worked at a movie theater for a few years in high school/college. Most of us employees were aged 16-25ish and were a bunch of immature jerks having fun while working and getting into trouble together after work. In the same shopping center, there was a fast food restaurant that a school friend of mine worked. Us theater employees would regularly walk over to said restaurant for lunch.

One day, like many others, we were making inappropriate jokes while cleaning a theater after a showing, and one friend joked about how he hadn't gotten any in a while. I jokingly volunteered my fast food friend to assist my theater friend with his "problem". Later that day we wound up at the fast food place for our break and, lo and behold, fast food friend was working. Their eyes met over the register and that was it. They got married the summer after we graduated. Eleven years and one kid later, they are still together.


23. Mental Gymnastics

My best friend had confusing feelings about this guy (he liked her tho) so she set me up on a date with him, we went to the movies, they get together like the week after because she got jealous about the date and realized she actually really liked him. They've been together for over a year now. Also wingwoman I guess


22. Connection In An Isolating Age

I felt like they fit so without asking her, I sent her picture to him on snapchat with a caption "oh I miss my bff" he immediately asked who she was and I said my close friend and oh by the way she's from the same town as you so you probably know her? To which he answered no but what's her name? So I told him and then I was like you know what? Maybe you should meet! So I gave him her number after asking her.

They didn't end up with each other though. They're now both married to different people.


21. C. Profit

A. Make this guy ask out all the girls in the school out. Obviously get told no

B.Girl takes pity and asks him out


i don't know why it worked it just did


20. Rebound


She was alone at the bar. A few friends and I were at a table having a few. One friend is getting over a breakup. We both need a new drink. I go up to the bar and order 3. Start talking to the girl. She seems nice. She's open to talking. And she's cute. Bartender brings back 3 beers. I wave my friend over. Hand her a beer. Hand him a beer. Get my beer "I think you two have a lot in common." and walk away. He got her number. They went on a date. It didn't work out cause he wasn't over his ex. But hey I tried.


19. Life Happening

My friend met a guy at my bachelorette party in a different city in 2002. They started dating immediately after. I got married, divorced 9 years later, was single for two years, dated a new guy for 4 years and married him two years ago. Those two are still together. And I'll be the first to admit I never thought they'd last. Good for them.


18. Now My Sister In Law

My first year in grad school there was a girl I thought would be perfect for my brother. So, I started joking with her that she was going to marry my brother. I sent around a picture of him one day when he was home from Iraq and she said he was cute. A few months later he was assigned to a base near her hometown. She went home to visit her parents and I sent them both an e-mail saying they should have coffee.

She married my brother.


17. We Will Never Know

One of my friends did this for his friend from home and I got to witness it first hand. A couple years ago in college, my friend invited me and a few other people to go to bars with him because he has a friend visiting. The friend's 21st was that weekend so he decided to wingman for the friend.

They both caught the attention of a cute blonde. Anyways, my friend eventually started making out with the girl but then 10 minutes later whispered something to the girl and the girl went to his friend and they apparently hooked up that night. My friends and I that tagged along were confused and shocked. If you ask him about it to this day, he doesn't remember because he was drunk and we will never learn about how that wingman technique worked.


16. Elaborate Lives

I walked up at our friends' wedding and started dancing with the girl that my roommate wanted to talk to. We danced for like 2 minutes and then I purposely cut myself out and redirected her to him instead. It was also an open bar, so at the time I was enough drinks in to assume it was a good idea. Low and behold, it was. They talked and got to know each other for about 2 weeks before realizing that their opposite life schedules wouldn't work out.


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 b 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 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 pleasing herself. Not just a little bit, but full on.

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 sleep with 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 sleep with me 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 basically 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 :')


Have you ever found yourself in an argument so stupid and/or pointless that you were sure you were being punked? Like you keep looking away from the other person to check your surroundings for places Ashton Kutcher and a camera crew could come popping out of?

You're not the only one.

u/Anti-hollowkid asked: What is the dumbest argument you've ever been in?

Brace yourselves, folks. Some of these arguments are breathtakingly bonkers. The sheer number of people who are willing to argue with someone over provable facts and what that other person likes or doesn't like is just ... stunning. It's stunning, you guys. Just not in a good way.

I Know What I Like


My wife and I once argued over whether or not I liked mustard on my hot dog. I was for me liking mustard, she was against me liking mustard.

The argument lasted way longer that you could ever imagine it would.

- AardvarkAndy

A Stair Step

My brother and I argued if our staircase had 13 or 14 steps, based on an argument about if the floor of the second floor counts as a stair-step or not. We still have no solution.

- RazerWolf04

My dad is a stairbuilder and I spent many summers working at his warehouse, so I can clear this up. 14.

- Apples9308


My husband and I have this thing where we only say "I love you" on Saturdays. Every other day it's "I love you, but only on Saturdays." I don't know how it started, but it's been going for 11 years now.

We're both shiftworkers, so sometimes we have to stop and think what day it actually is. We had an argument recently over whether it was Saturday or not. I said it was Saturday, he said it was Friday. It was Monday.

- FormalMango


I remember when I was about 13 my parents had an hour-long shouting match that ended with them almost getting divorced. The issue? Whether or not the nation of Iraq has a coastline.

My mother arguing that Iraq had a coastline, while my stepdad argued that it did not. This was back in 2004, and they are still quite happily married to this day. That incident is something they look back on and laugh about, and both of them admit it was really a pretty stupid thing to argue over.

- dontcryformegiratina


With an ex:

"I owe you $80 for the bills of ours that you pay, and you owe me $40 for the bills of ours that I paid. Here's $40 in cash; we're even."

She did not understand this.

I literally had to go get another $40 out of the ATM, and hand the $80 to her. Then I had her hand me the $40 she owed me.

"Now how much do you have in your hand?"

She still didn't understand.

She somehow has a college degree.

- Speedly

Mini Wheats

When we were kids my brother and I got in a physical fight because he said I like mini wheats and I insisted I didn't. His argument was that I always sang the mini wheats song and I was deeply offended that he wasn't aware that it was just stuck in my head but I hated the cereal. I actually did like the cereal I'm not sure why I was arguing with him about it but I remember how genuinely angry I was.

- shicole3



I'll tell you about the only legal trouble I've ever been in, the fight that got me arrested. It started over whether we should return a box of crayons or not, and to this day I don't have any idea how it escalated to the point of the cops being called, but they were and I was the one taken in.

- CorrectionalChard

That's Unfair

My boyfriend insisted that when two people are in an argument and one makes a point so reasonable and logical the other one can't disagree with it - it's unfair. I tried, logically and reasonably, to explain several times why that is just winning the argument, proving your point thoroughly and is completely fair.

His answer was that I was being unfair.

- ShyAcorn

Pure Masochism

How the ch in masochism is pronounced. My friend caught me saying "masoKism" while he would say "masoSYism."

To be fair, he grew up speaking French, in which the ch in masochism is pronounced in "his" way. But he insisted that I was the wrong one here and that was just infuriating.

- argofire

Emailing NASA

A woman was adamant that looking at the big solar eclipse on the television was unsafe unless you were wearing glasses. She wouldn't believe us and insisted on emailing NASA to check.

- derawin07

A Non-Standard Ruler? 

I worked for a company that made signs. We had a customer ask for signs that were 7mm wide that were to go on a door. Our sign makers figured the order meant inches because 7mm is pretty small, so made them 7 inches. I got a phone call from the customer who went mad at me for making them the wrong size. So I put a reorder through for 7 mm.

Argued with the sign makers over it but they eventually agreed to do it after I shown them the order in writing. I even had the customer put her complaint in writing, reiterating the size they wanted.

7mm signs went out and a day later I get the customer on the phone literally screaming at me.

Cue the dumb argument - we ended up having an argument over how big a millimetre is, and obviously everyone in the office were laughing, but this customer just wouldn't accept it and said we must be using a non-standard ruler to measure.

Ended up being escalating to the sales department manager who refused to issue a refund. We still don't know what they actually meant.

- Lovelocke

This Unusual Vegan Argument

Was in a pub with a few friends, and some random Dude dropped an ear, and somehow figured I'm vegan. Well, people like him are the reason I usually avoid mentioning it. He came up to me and insisted on starting a discussion about veganism. He claimed that by the end of it, I would be eating meat again.

He listed some stupid arguments, I told him I was not convinced and then tried to keep on drinking beer with my friends. He followed me, and wanted me to "try to convert him to a vegan." I stupidly listed some of my reasons thinking it would make him go away. He told me he still was not convinced, so I was like whatever. Again, I really just wanted to drink beer with my friends.

That dude followed me all night and expected me to try make him vegan. Doesn't matter what I said, and all the reasons that for me are obviously good enough to be vegan. He'd be just like "No, that doesn't convince me, therefore your argument and how you life is stupid."

Didn't matter how often I told him that I honestly don't care; 5 minutes later he would come up to me again "I'm still not vegan, so veganism is stupid, all your arguments were stupid, now give me a good reason to become vegan!" At one point, I was literally yelling at him that I don't give a single flying f about what he eats and why, that it's in no way my responsibility to "turn somebody vegan" and in no way his business what I eat.

Honestly, for that dude, I would have bought a whole ham, just to shove it up his stupid annoying face.

- onlytruebertos

Monty Python

In college my roommate and I argued about a line in Monty Python & the Holy Grail. The scene with the Black Knight where the line "Alright, we'll call it a draw" is uttered. We argued about who said that line, whether it was King Arthur or the Black Knight.

It went on for hours longer than it should have because I was stubborn and refused to admit I was wrong.

- Skrivus

Albert or Arnold


Whether Albert Einstein or Arnold Schwarzenegger would be more useful to have around during a Zombie apocalypse. How on earth would Albert Einstein come in handy!?

- Gerrard1995

Below Sea Level

I live on an island and when you go upland and you look out the sea looks like it's higher than or on the same level as the land. It's just a weird perspective thing because of the horizon. One day some kid says that it's because the island is under sea level.

I'm like wtf bro all of us would be with the fishes. He argues that no that's not true and if I just go upland I'll see. We then spend a good 5 minutes of my time arguing about it until I decided to leave this kid in his stupidity. He even said we shouldn't believe everything adults tell us and sometimes we need to think for ourselves.

This kid was older than me and was going to a good school. Lost my respect for him ever since then.

- -justforclout-


Someone tried to fight with me over how to spell my name.

Now, my name is in a lot of languages with slightly different spellings. I would have accepted any of those spellings, but this one was just... Not even close. It didn't make any logical sense.

An analogous example is if my name was Thomas and someone was insisting it was spelled Tomash. And not just the name Thomas in general, but that me specifically, on my birth certificate, was named Tomash. I know how to spell my own name.

I swear to god, it went on for like an hour.

- TK-DuVeraun

Whales Are Mammals

I was in an online chat room one day, and we were talking about whales. I commented on how whales are mammals and the next thing you know, someone was arguing with me and trying to convince me that a whale was a fish.

- kawaii_psycho451


Stupid microwaves. Having a man child talk down to me about how microwaves work only for him to google it and prove me right. He slept on the sofa that night.

- sun_phobic

Shower Schedule

My friend keeps telling me that the norm is that a person should shower once a week. This has been going on for years. I'm almost convinced he's trolling me.

- LibrarianGovernment

No Balloons For Grandma

My cousin and I argued over a balloon going to Heaven. We were at his big sisters prom send off and he let a balloon go and it went high into the sky.

He then said this balloon will go up past space and go to Heaven and reach grandma (God rest her soul). And I was like no it's not and it's probably not even gonna reach space. Releasing balloons is terrible for the environment and kills/harms so much wildlife.

He got really mad and defensive and started telling me to google it and do my research and I'm like I don't have to google it you idiot. He was mad at me for a good week.

- Dskee02

Spontaneous Dolphin Existence


How dolphins reproduced. It took me a few solid minutes of explaining to her that dolphins have reproductive organs and that they did not just pop into existence. The argument began with her saying she wanted to work with sea creatures.

Personally, I hope she was messing with me cause I lost a little faith in humanity that day.

- thebeststory

Male Chickens

I repeatedly had the argument with a friend over whether roosters were chickens. She was convinced that only the females were chickens (hens). We were 18 at the time.

- bee_zah

Lightning McQueen

Me and my friend were drinking underage, we ended up in an argument of whether lightning McQueen's eyes were blue or green. Somehow throughout the whole thing both of us never thought to straight up google a picture.

- 23071115

But ... Ice Floats

Waiter/Host here.

Woman wanted ice on the bottom of her drink.

Now read that sentence again and try to imagine arguing with that particular brand of stupid.

- FarWoods

Time Zones Exist

Coworker claimed that it was the same time of day and the same season on the whole globe. Had to get 4 coworkers to confirm to him that time zones do in fact exist.

- JustARegularToaster


My brother is colorblind. And he CONSTANTLY tries to correct me on what color things are.

"Hey could you hand me that red _____?"

"that's orange"

"no, it's red"



It is the base of our most common and heated arguments.

- droneb2hive

Andre 2000?


I'm late, but I saw this question and instantly remembered that I was booted from a Facebook group because I called someone out on a lie that was not only bull, but extremely pointless. She was friends with the moderator and they made the case that my argument over such a little lie was more of a problem than the lie itself (though they didn't refer to it as a lie.)

The woman said that she used to babysit for Andre 3000 and that his name was Andre 2000 - but he changed it after the year 2000 had passed. This was so easily disproven it was ridiculous. Their debut album came out in 1994 and he was already going by Andre 3000 at that time.

The argument wasn't a huge long drawn out thing, but the fact that either of us were on Facebook at separate times meant that the responses were over a long period of time so this argument lasted a few days.

It was stupid.

- P1ST0L_Wh1PP3D

Stars Like Our Sun

I was arguing with my grandpa about stars he didn't believe that there are other stars like our sun. Basically he thought there is only the sun, the moon and the earth.


Richard Nixon

I have a degree in history. I mostly focused on nationalism. Wrote a 50 page paper on it and Richard Nixon with around 50 100 sources. Looked at micro film for hours on end. Part of the paper focused on how Nixon being chair of the house committee of Unamerican Activities was used as a powerful weapon to use against political enemies. It also inspired Joe McCarthy. Have had people tell me I was wrong and Nixon was never elected to a position besides the president and Joe McCarthy came before Nixon. I stopped trying to talk history to people.

I also know quite a bit about the history of the Balkans its amazing how many Serbs refuse to believe Tito did anything wrong.

Wrote 100 page paper on nationalism in Israel. Its frustrating to talk about because for some reason a lot of people think Palestinian firing rockets randomly into Israel is ok but if Israel retaliates the people get up in arms over a targeted air strike that kills 3 people.


Balloon to Heaven

My cousin and I argued over a balloon going to Heaven. We were at his big sisters prom send off and he let a balloon go and it went high into the sky. He then said this balloon will go up past space and go to Heaven and reach grandma (God rest her soul). And I was like no it's not and it's probably not even gonna reach space.

And he got really mad and defensive and started telling me to google it and do my research and I'm like I don't have to google it you idiot. He was mad at me for a good week.


Binder Clips

I got into an argument with a co-worker over how we were attaching two pages of a letter together: small binder clips or paper clips.

He felt that paper clips would leave a "dent" in the paper when removed, but binder clips won't. He refused to staple them together. I felt that binder clips would also leave a "dent", so we might as well just use the paper clips.

It ended with him saying: "Do what you want [me], I don't care!" and storming off.



Once got accused of faking being Jewish. Why? I have no clue. We argued over the course of a month, any time I'd bring it up and she heard about it, she'd begin going after me for "faking it".

My mother's side is ethnically Jewish. Grandparents were practicing.




3 friends and I once got into an argument about how to pronounce Nutella. It lasted for about 3-4 months. It was hilarious how serious we took it, it'd get heated but never for real serious.

I think someone even called the company that made it to check, or that may have been for the Cheetos company. We were really bored in high school.


Lingerie Boxes

Late to the party, but there it is.

I'm a manager at a small store. We're only 4 working there, so my team and I grew very close and we joke around a lot. Once during a slow shift, my employee and I had an argument because we were looking at the lingerie boxes, and I thought that two specific boxes had the same woman on it, but she was 100% positive they weren't the same person.

Looking back, I don't know why it was such a big deal to us at the time, but we even called another employee who lives across the street to come and tell us what the heck was up with that. Turns out I was right, and she was pretty salty about it. It was a great night.


Wicked Witch of the West

I almost got into an argument with an old girlfriend over Glinda the good witch from Oz. She insisted that Glinda was manipulating Dorothy to assassinate the Wicked Witch of the West and convince the Wizard to leave to create a political void she could fill.

I conceded the issue when I heard the whole premise because I thought it was too damn stupid to get worked up over.


Keep Your Hands to Yourself

Just the other day I legit got in an argument with my co-workers on why I don't like my butt being grabbed by anyone (I'm a guy). Seriously.

They went on about "I don't mind it. Mike and I do it all the time and we don't care." Yeah, that's nice dude, but I'm not you, and there's something called "Keep your hands to yourself" (which was taught to a good portion of us growing up). Just like how Karen wouldn't like it if I touched her boobs or her grabbing your crotch or frankly ANY area you wouldn't like being grabbed, keep away. In general, you should not be touching me in any areas after I've told you not to several times before.

So unless you're sleeping me or dating me, keep your damn hands off my toosh.



My best friend and I argued over whether or not telekinesis was possible. Her argument was that humans don't yet know what the human brain at 100% usage was capable of, and that telekinesis was inside the possibilities.

I said the brain does use 100%, just at different times.

We didn't speak to each other for four days.



How dolphins reproduced and whether or not ghost existed (back to back with the same person). It took me a few solid minutes of explaining to her that dolphins have reproductive organs and that they did not just pop into existence (the argument began with her saying she wanted to work with sea creatures).

How it shifted to the existence of ghosts is a solid and reasonable question to ask (I don't remember why). I had to then proceed to tell her that ghost hunting TV shows do not constitute as undeniable evidence.

Personally, I hope she was messing with me cause I lost a little faith in humanity that day. This was in high school SO... hopefully she was kidding.


Dogs and Chocolate


I told this stupid woman that chocolate is toxic to dogs. She went on to tell me how a little bit will just make them hyper and then they will calm down. I told her to google it. Her and her bf shut right up. Now they have a kid. Good luck, Jeremy and Andrea. morons.

I should also add that this argument started because Jeremy was giving his tiny dog chocolate and I told him it was toxic.


Is water wet?

My roommate and I have a recurring argument over whether or not water is wet l, and whether or not a person is considered wet underwater.

For the record, it is no to both questions.


Mission Trip

A kid a church telling me about the mission trip I went on. Not only was I not on that trip, but I had never been on any mission trip. We were good friends, so it's not like he would've mistaken someone else for me.

He insisted I was there as if an entire week long trip would just fall out of my memory. He even had stories of things we'd done together. I'm not sure if he thought I was lying, joking, stupid, or crazy, but I was pretty sure he was some combination thereof.


Dragon Tales

One time I got into a shouting match with my mom and little brother in the car. The issue? The names of the two-headed dragon from the PBS kids afternoon show Dragon Tales. I swore it was Zack and Macie.

It was actually Zak and Wheezie. I don't even remember why we were yelling about it.


Green Or Yellow?

When I was about 15 or so my mother and I spent about 20-30 minutes arguing about the color of a shirt. We agreed it was blue/green, but to me it was just a shade more blue, while to her it was just a bit more green.

Turns out, your eyeballs yellow as you age and hers were 24 years yellower than mine, so I think that skewed her color vision.


Stars In Their Multitude


I once got in an argument over whether or not a line from the song "Stars" in Les Mis says "...but mine is the way of the lord" or "mine is the way of the law".

I didn't even really care what he thought but he was so adamant and cocky that it got me heated. By the end of it we were shouting at each other and I had to apologize, which I think is what he wanted the whole time.



My brother is colorblind. And he CONSTANTLY tries to correct me on what color things are.

"Hey could you hand me that red _____?" "that's orange" "no, it's red" "orange" "YOU CANT EVEN KNOW".

It is the base of our most common and heated arguments.


Hot Water

About five years ago, my girlfriend (now wife) once had a very intense argument about whether or not hot water cleaned things better than cold water.

She genuinely believed that water temperature didn't matter. This is someone who has not one, but two masters degrees.

We argued for something like 2 hours, and we seriously almost broke up over the whole thing.


Biology Class

I had an argument with a girl IN THE MIDDLE OF A BIOLOGY CLASS in high school about how humans are not mammals. She thought a human was a human and we are not mammals because "mammals are animals and humans are not animals"

I tried explaining to her the difference between reptiles and mammals and how humans fall under the mammal category to try and educate her... but she just wouldn't listen.

I still have no idea why the BIOLOGY teacher did not get involved...


Solid Or Liquid?

Some classmates and I got into a heated debate as to whether or not the human body could count as a soup, salad, or sandwich. The teacher got mad at us, but hey! All we were doing was watching a movie.

For the record, my logic lays with soup- Liquid contained within a solid, at a hot temperature.