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People Admit Their Most Embarrassing Flirting Fails

Mathew Burke

If there is one among us who actually knows what the right thing to do is when they have a crush on someone, let him or her speak now or forever hold their peace. Either way, I am sure that most of us know what not to do under such circumstances.

Sadly, the same cannot be said for the following 42 individuals. Here are the stories of how each of them, in their own unique ways, turned attempts at impressing would-be significant others into lifetime memories that they’re still trying to live down. And for the love of all that is good and sacred, do not try these at home!


41. No Second Chance at Making a First Impression

Was at a festival, and went over to talk to a girl I was interested in. For some reason I tried to get her attention with a water bottle, that was unknowingly open. I completely soaked her with it. There is no coming back from that.

AzusmattyboyTM

40. C’est la Vie!

I was about 18 and trying to flirt with a guy who I was sure had a French accent. I wanted to ask where he was from, and said, “Je suis de France?” which, unbeknownst to me at the time, means “I am from France?” He was completely unamused and goes, “I’m from Hungary.” Ten years later and I’ve never tried to speak French again. Or Hungarian.

somegirlyaknow

39. When One Door Closes, Another One Opens

I was talking to a girl and her friend in a nightclub and it was going well so I figured I’d whip out the ol’ iPhone 3G (long time ago I know) to ask for her number.

I was far too enthusiastic and it went flying out my hand and landed on the floor and reset so it displayed the Apple logo.

I just picked it up, sighed, and said “Nevermind” and walked away with my shame.

Little did I know the girl who is now the mother of my child watched it happen and was laughing from afar.

blazingwhale

38. What a Joke!

When I was in middle school I had a crush on a girl, so I decided to write her a love note. I googled “love poem” and wrote down the first few poems that came up. At the end of the note I wrote “will you be my girlfriend?” Well since I was an awkward kid, when we were leaving school the next day I gave her the folded note and told her “read this, here are some jokes” and went home. I then went to school the next day as if nothing happened and I never asked her anything about it since I was too shy.
We still talk sometimes and that was never mentioned again.

sapelgas431

37. Lollipop, Lollipop, Oh Lolly Lolly

My college crush and I were riding in the elevator and she was sucking on her lollipop. She looked at me straight in the eyes and asked me if I wanted it, pointing the lollipop at my lips. I said, “Nah, I’m good.” Elevator opened on my floor and I went to class.
I strongly hated what I did for the rest of the semester.

HTPark

36. I Can’t Be-Leaf This One!

I took a solo trip to Toronto to see my first Leafs game and get away for a bit. I like to spend my vacations just walking around a city, riding (relatively) decent transit, maybe smoke a couple joints, and eat good food.

It’s my second to last night there and I was going to Greektown cause Greek food is the best and I hadn’t been yet. Got maybe four joints rolled in my cigarette pack, ready to go. Stop in this slightly classier place (but still relaxed enough to seat me wearing my Leafs hoodie) with decent reviews. My waitress was this tall redhead, just gorgeous.

She was super nice and we talked a bit about the Leafs, how my vacation has been, what I should do the next day. You know, the regular server stuff. Had my fantastic meal, ouzo to finish, and left. I go to grab my smoke pack to find it’s not in the hoodie pocket, (oh no). I must have dropped it somewhere.

I walked a little bit back the way I came in case I dropped it before I went in and hoped by some miracle it hadn’t been picked up but no luck. So thinking maybe I dropped it in the restaurant I went back to see if I left it there or if it was under the table but it wasn’t. I think it was about an hour before closing, and she walked out the door with me as I expressed disappointment at losing my joints.

“I’ve got a couple in my car if you want to come back for one”

“Nah,” I answer, “I’ll be alright. I’ve got some left in my room, thanks though.”

“Are you sure?”

“Yeah, no worries. Have a good night.”

I got off the subway at Union and my brain said: “You dummy, a stone fox who knows you’re here to get away from regular life and leaving in 36 hours, is clearly 420 friendly, and near the end of her shift invited you to her car for a joint.”

I’m willing to accept that she was just being nice cause she’s a server and I’m a pretty easy customer from out of town, but I’ve run this story by a couple friends and it’s always ended with them saying “You dummy.”

About two blocks away from the restaurant after I left there was an unmistakable smell in the air, I wasn’t getting my joints back; I guess a couple of the homeless around there had a better night than usual so I’ll take that as a win.

ninj4b0b

35. Should I Take Your Word For It?

I got you fam.

I had a very pretty friend of mine from college stop in town and call me to catch up after work. We go to happy hour and she starts talking about how she has only slept with one guy and she wants that to change. She then goes on about how her friend I had slept with had a very high opinion of me.

We put back a few drinks and then I left because I had to get up for work the next day. I told her she was really pretty and shouldn’t have any trouble hooking up with a guy of her choosing.

A year later it dawns on me…

I swear I’m usually not a social idiot.

Thebanks1

34. Nice Try, Mother Goose

I liked this girl named Sydney and I was like “you know, Sydney and pretty rhyme for a reason :)” and she was like “Sydney and pretty don’t rhyme tho lol.” It was the biggest L of my entire life…

TwainZ__

33. I Have a Feeling She Didn’t Mean a Cake

I had a girl at a birthday party suggest we go to my room so she could give me my “birthday present.” I just laughed it off and walked away.

I did end up having sex with her, but I didn’t get what that meant until like a week later.

Heroshade

32. Different Method, Same Result

Does sending her a five paragraph long email describing how madly in love you are with her count?

I don’t know if it necessarily counts as flirting, because it wasn’t subtle, but it definitely failed lol.

DoritoKat

31. We’d All Like to Erase This Memory…

In year one there was a girl I had a crush on, and in my little child mind I thought a good way to get her to like me back was to leave those Smiggle erasers that you put on the end of your pencil on her desk. Smart little child me forgot to actually think about how that would work, since she had no idea where they came from and just gave them to the teacher because she thought someone lost them.

BlaMU

30. The Jig is Up

So back when I started learning how to flirt, a few prior successes made me decide to try my luck with this intimidatingly hot girl. So I walk up to her brimming with confidence, tap her on the shoulder, she turns around and I said “Hey” with a raised eyebrow. She’s looking unimpressed so I follow up “Why would a girl like you feel the need to hide that pretty brown hair?” (her hair was black at the time).

She’s smiling, now I’ve got this. She gets really close to me all giggly and bright eyed asking how I knew her hair was brown. Her hotness shatters my false confidence and I start mumbling about her having freckles, genetic impossibilities, and deductive reasoning… it was all downhill from there.

Not-an-Ocelot

29. An Unmistakable Strategy

All my flirting is like the Kool-Aid man, in my mind I break through the wall shouting “OHHHH YEAHHHH,” but in reality I’m broken and drowning in my own blood.

ancientkillerX

28. Well, That Was a Bold Move…

Not me, but a guy I sort of had a crush on totally failed at trying to flirt with me. We had been flirting and bantering back and forth for months and nothing ever came of it. But one day I ran into him when I was shopping at the grocery store he works at.

We had not seen each other in like six weeks at this point so we hugged and made small talk. As we were hugging to say goodbye he turned his head and full on licked my face. It was incredibly strange.

salutbrooke

27. Why Did It Have to Be Twice?

Cute bartender I’d been lusting after brought me a drink and sat down with me. I freaked out so bad I spilled the drink on myself TWICE before I actually managed to get any of it in my mouth. Sigh.

Permalink

26. Like Taking Candy From a Baby

I was a not-so tactical kid, so I put a piece of candy on a doorknob, approached the girl I liked and told her there was something for her “in that direction” and walked away before I could even see a result.

angry_snek

25. Take It as a Learning Experience

Messaged a girl on Facebook when I was about 14 saying “You’re really cute.” She messaged me back “You’re really not, bye!”

14-year-old me was heartbroken.

stonerplumber

24. Cut it Out!

Sent a note to a boy in first grade. “I think you’re cut.” The fact that I could correctly use “you’re” and yet misspell “cute” is beyond me…

snixone6

23. The Only Option to Explain This One is Poor Word Choice

Accidentally told my boyfriend I was dating him because “[he was] my only option.”

What I meant was “you’re the only one that gets me and the passion + commitment we share is so far above anything anyone else could offer that dating other people is not even an option anymore.”

22ndsol

22. Won the Battle, Lost the War

The first time I had a flirting fail was many years ago when I would walk to my work a couple miles away from my place. A girl I worked with offered to give me a ride, even though I could clearly already see my destination from where I was. She was persistent; as was I. I won out, but came to find out, I had truly lost. She wanted to give me a ride specifically so she could get romantic with me in the car.

ProjectShadow316

21. Second Time’s the Charm?

The second time I messed up in a flirting situation was when I was out with a recreational sports team of mine. I had walked there (20 minute walk; I needed the exercise), and she offered me a ride back. After being persistent, I relented this time. I thought she was into me, and I asked her out to dinner after we got to my place. She loved being around me and all, but just wanted to be friends.

ProjectShadow316

20. Finding Common Ground

Found out halfway through what I thought was a date that she was a lesbian (I’m a guy), and had thought we were just going out for a drink as friends. To be fair, we’re still friends years later. We bonded over our shared taste in women.

lagoon83

19. This One’s On You, Man

I asked this girl for her number and forgot to note it down.

Safe to say, didn’t get a date.

ancientkillerX

18. Not the Result You Were Expecting…

Tried hitting on a group of female cheerleaders, a male cheerleader was also there.

Ended up talking to the male cheerleader about how to get pretty in the morning.

inabackyardofseattle

17. Was It At That Point in the Conversation That She Said She Was Busy?

There was a time when I went to go get drinks for some girls, so I bought us a bottle of wine and got distracted by the football game. They came in like 20 minutes later and I’m just sitting there with a bottle of wine and four glasses completely ignoring them.

And at one point later they were talking about how aprons are unattractive and I started talking about how I had to wear one so I didn’t get all covered in blood from all the animal carcasses. I went into great detail about that one. I was a butcher for a while and I was pretty passionate about it.

Sadly, I have too many of these to count.

v******carnage

16. You Really Dodged a Bullet There

I had been invited to go with a friend to Chicago. We brought along a friend of hers, but someone I hadn’t ever met. He was a cute guy though, and we talked a lot, had a lot of similar interests.

At one of the museums in Chicago, my friend wanted to go see a deep sea movie, and I… can’t do anything deep sea. Her friend offered to stay outside with me so we could both go look at the Lascaux cave painting exhibiting, which was VERY exciting to me. It wasn’t all just about the cave painting, but about ancient life, knapping, hunting, the way they made things, etc…

So I, not being able to control myself because I have zero social knowledge and I’m also yeehaw country, at the exhibit about hunting specifically, ask this very cute guy I am very interested in if he knows how easy it is to skin a deer. He looks at me. I look up at him and keep. Going. My brain is screaming at me to stop but it has no control over my stupid honky mouth.

“Simple as getting a truck, a knife, a rope, and some rocks! You cut around the neck, make a kind of ruff, and tie the rocks into that? Then you tie the other end of the rope to the truck and drive slowly forward. It comes off like a sweater!”

This weirdo dated me and married me instead of running for his life.

Four years married this May. Love you forever, babe, through brightest day and blackest night.

Okay, okay. In the long run, this was CLEARLY not a fail. I get it! But I definitely didn’t know that at the time!

rainoverorgonon

15. The Sounds of Silence

She was talking about Alaska and jokingly said she thinks her dog could run in the Iditarod. And I responded with, “Hey, just like that one book we had to read in middle school! Stone Fox! Wait, but not the ending.”

And we sat in awkward silence for a few moments as I realized I made her visualize the death of her dog that she loved so very much.

LegendofSki

14. She Should Have Been More Patient With Her Response

So I’m a nurse and there was a coworker I was crushing on pretty hard. He had a bottle of Diet Coke or something similar at work one day in which he took one sip out of it, then asked if I wanted to share it with him. However my dumb self misheard him, and I thought he said that he picked it up out of a patient’s room and that he saw the patient take only one sip out of it so it was “barely used.”

The thing that I misheard was that he said he took a sip out of it, but I heard a patient did instead. I had no idea he was drinking from this bottle, and I thought he was offering me a random patient’s bottle of Coke who went home. I proceeded to belt out “EWW! Heck no! What’s wrong with you?!” while laughing pretty hysterically.

He looked so sad after that but I couldn’t really understand why until later that night after he went home and I replayed the situation in my head and realized that I completely misheard him.

Pink_Sprinkles_Party

13. Love At First Sight

Not me but this story fits and I love it.

It was probably 1968-ish and my mom was in high school. She hated cigarettes because her whole family smoked, but nevertheless she wanted to impress this guy she liked who smoked. So she borrowed a cigarette from her sister, lit it and walked over to him. She took one puff and threw up all over him.

That’s how my parents met. They were married for 39 years.

Mortico

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12. Dart of the Deal

Oooh about a decade ago when I used to smoke, I was on the rooftop of a bar with the rest of the smokers when a girl came over. She offered up a dollar for a cigarette, which was pretty common. So I said “I’d rather get your name than your dollar” and she said, “I’d rather just give you the dollar.”

It’s not like I had the “A” game or anything but it happened in front of everyone I was there with. She won, got two darts and I didn’t take the dollar.

mydogisamy

11. Don’t Be Cruel to a Heart That’s True

Not really a flirt, but I finally got up the courage to tell the pretty girl in my class that I had a crush on her. She told me she needed to think and I went back to my desk, heart pumping so fast I could hear it. She walks over and says, “You wanna be my boyfriend?”

“Yeah!” I said excitedly.

“Ok, well now I’m gonna dump you.” I look over and her friends are snickering in the corner while she laughs in my face and walks off.

Didn’t ask out another girl for years. Secretly thought all girls were horrible for a while. Feels bad man.

Jaymezians

10. Well, That Came Out Wrong…

I’m female. I wanted to try to flirt with the cute cop guarding my work building, so on my way back from walking in the rain without an umbrella, I tried to make small talk about the weather. What came out instead was:

“In case you didn’t know, it’s raining outside. Just take a look at me, I’m nice and wet.”

His face turned bright red and once I realized what just came out of my mouth I stuttered something like “no, no, I mean….uhhh.”

And then I ran up to my office and hid the rest of the day. Never saw him again.

leashyb

9. Always Think Before Speaking

Feeling I needed a neutral opener to start the conversation, I approached him and awkwardly started talking about someone else we both knew. He just thought I was being nosy and gossipy, and told me I should shut the hell up and mind my own business. Ouch.

I wasn’t intending to gossip, and didn’t say anything bad about our mutual friend; but with hindsight, I can understand why he wouldn’t have appreciated my approach. I should have tried to find any other common interest, but I was nervous and didn’t know how to initiate a conversation.

Also, to clarify, I’m a guy.

InbhirNis

8. Take the Hint, Fella

Biggest fail of when someone was trying to flirt with me: I was leaving a party in college, a cute girl offered to drive me home, I said no because I lived one block away, she was persistent, so was I…

Took me a couple of days to figure that one out…

TheCSKlepto

7. Talk About Bad Timing

Was hitting on this girl in college, was at a party we had going on in one of the halls (end of the term I think).

Things going well, both having drinks and stuff, just as I’m starting to “make a move in” for a kiss this guy walks past with his girlfriend on his shoulders and the girl I’m flirting with goes “I wanna do that.”

So, very drunken me picks her up, proceeds to walk her straight to the next hall, then I trip, she slips down and falls flat on her face, lots of blood pouring from her nose.

I stand up to see her on the floor like this, and stupidly say “your face looks bad.”

She never spoke to me again.

zornyan

6. A Little Elbow Grease Isn’t Always the Way to Do the Job

Went to put my arm around a girl and drilled her in the nose with my elbow.

ShlomoKenyatta

5. Straight to the Point

I was working at Tim Hortons when I was 16. I’d had a crush on this one regular who was much older (40 or so.) After filling his order for a dozen donuts, I slipped him a piece of paper with my number. My hands were shaking and I couldn’t look above the visor of my hat. He declined and just said flatly, “Too young.”

neptunesunrise

4. At Least She’ll Always Remember You

When I was seven I had a crush on this girl in my class. I was the only boy in the class who actually liked girls by this age and I tried to hide it. At the same time though I really wanted her to be my girlfriend, whatever seven-year-old me thought that entailed.

So I tried a bunch of different things, I invited her to my birthday party, where my brother made fun of me the whole night, I always picked her when we played seven up, stuff like that. My favorite was when it was Valentine’s Day and I wanted to impress her, so I tried to smell really good, I didn’t own cologne because I was seven, so I covered myself in baby powder. No joke like head to toe underneath my clothes were covered in baby powder.

On top of that, I made this huge Valentine’s Day card that had this picture of me and her holding hands I drew myself. When it came to hand out the Valentine’s, we did, but I was so nervous when I did it, and everyone started mocking me saying I had a crush on this girl. It all became a little too much for me and I vomited… right onto my crush.

As if that weren’t enough, upon realizing my mistake I blurted out “I’m so sorry, I love you!” as I was trying to clean the vomit off of her with my bare hands. Safe to say she didn’t feel the same way.

_will_sex_for_food

3. Prehistoric Mistake

Fancied a lass for ages. I was around 23, she was 22. We were heavily into raving/clubbing at the time, to Hard House specifically. Now, this girl Steph was really pretty but had a very unique bone structure to her face, the type models have.

So I was pretty smashed one time when we crossed paths in a club and small talk ensued, so I basically said “Steph you are really hot and unique looking, you have the bone structure of a velociraptor.”

She was genuinely horrified and we spoke very little after this.

Ph0en1xGeaR

2. Brace Yourself: This One Is Rough

I was like 11 on the monorail at Disney. There was a girl I thought was pretty but I couldn’t think of anything to say. Right before she left for her stop I just said: “I like your braces.” She looked at me like I had a third eye. My dad had a look of disappointment. It’s a moment that still haunts me.

HotforSega

1. That Is Quite the Freudian Slip!

I meant to say “hi” or something but his arms were so beautiful. I ended up saying “biceps.”

FamiliarNameMissing_

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