31 Cringeworthy Flirting Fails That Will Destroy Your Faith In Humanity


1. The Braggart

Overheard some kid at my university – who’s pretty obviously well off – trying to impress a chick with all the people his dad knew and places he’d stayed over summer.

Her response?

“Wow, that sounds really significant.”

Clever girl.

2. Girl Baiting

I had a roommate who would do this move after we had a party and there were people lingering … He would go up to a girl and go “Alright, I’m going to bed. Goodnight.” and then walk off.

Then about 2 mins later he’d have come back up to “get something” and be like “Man, I’m tired. I’m gonna just pass out” either right by the girl or where she would hear.

Then 4-5 mins later he’d come back up to “do something” and say “I might just watch a movie or something before I fall asleep”‘ the he’d wander off.

This sort of thing would continue. His plan was obviously that eventually, a girl would come with him. AWESOME PLAN.

Now for the wtf part. I saw this actually work at least 3 times with 3 different girls,and it may have persisted after I moved out. All three times I witnessed ended in “relations.

3. The Gnome

Overheard this guy just randomly sitting down next to this pretty girl in a Starbucks in San Francisco.

The guy wastes no time in whipping his laptop out, then saying to her “Hey do you like WoW? Let me show you my Gnome Tank!”

That poor girl looked so… Shocked and confused. And everyone in the queue had to try to hard to suppress the laughter.

(I mean Gnome? Really?!)

4. Missing The Hint

I was at a gay bar a couple months ago. There was this guy wearing the exact same shirt as me. I go up to him and say something like “Cool shirt!”

He responds: “Looks better on you.”

My drunken response: “I know, but you look ok in it.”

Run away.

5. The Manga Lover

A few summers ago I was on a business trip, catching a connecting flight in Pittsburgh. Some fat sweaty old guy in sweatpants who had been reading NSFW manga in the terminal for about half an hour starts chatting up this young woman. He asked her if she was planning on going to something called anthro-con and then showed her the contents of what looked like a sketchbook. (I couldn’t see, I was facing them.)

I’ll never forget the look on her face. This continued until boarding.

6. Overkill

Was at a wedding a few years ago. Bunch of single guys went out drinking afterwards and we were all pretty loaded. One guy is striking out all over, so decides to take it to the next level. Walks out onto the dance floor, whips down his pants and yells, “All right, who wants some of this.” We all left that bar soon after.

7. No, Just No

Girl sitting by herself on a couch just inside during a houseparty/backyard party. Diddling on her phone and what not. My friend walks in, sits next to her, puts his arm around her, looks her in the eyes and says “I have a girlfriend but she says it’s okay if I make out with other girls.” She just gets up and walks away.

8. B Squared

On my first night away at college i witnessed the most horrific attempt at flirting I’ve ever seen. There’s five of us in the basement of our dorm one night, we’d been drinking and it was very late. It’s 4 guys and one girl and were just hanging out talking on the couches. This random kid comes downstairs without saying anything and plants his ass on the couch directly next to the girl. He starts small talking her, like “whats your name” “Where are you from”, standard small talk. I glance over at one point and notice he has A RAGING BONER. He was wearing track pants so that mofo was sticking up like the eiffel tower. I look around our circle at everyone else and they’ve clearly all seen it too. From that day on, we referred to him as boner boy, or in short, b squared.

9. “No Thanks”

My flatmate who’s a girl. A guy offers her a drink. The following was how the conversation went:

Him: “Can I buy you a drink miss?”
Her: “Not if I buy you one first.”
Him: “No, thanks.”

He proceeds to GTFO of there.

10. The “Bad Guy”

Coworker who I barely ever work with knows I moved from 2000 miles away to live with my boyfriend, tells me I’m cute. Fine, whatever. Then later tells me he like me because I’m a “good girl” and “bad guys like good girls.” I tell him good girls don’t like bad guys, which is why I’m with my boyfriend, who is incredibly nice. He proceeds to tell me that he’s sort of good, like he may sell drugs but he’ll also help little old ladies cross the street. SERIOUSLY. HE SAID THAT.

…Then he asks me what happened to my hand (I’m wearing a wrist brace.) “I don’t know, I injured it.” he says “Masturbating heavily?” in front of our boss.

Are you fucking serious?

11. “Up Yours”

A friend of mine was drunk one night when a lovely young lady caught his eye. He wandered over to her and he wanted to say something along the lines of ‘Here’s looking at you kid’ or just simply ‘cheers’. Instead he just looked her in the eyes and roared ‘Up yours!’

12. “Not My Best Moment”

I once tried to tell a girl she had really pretty eyes, it came out as “woah you have HUGE pupils” not my best moment.

13. Shitty Drunk

My one buddy was shitty drunk at a party. He sat down on the couch next to a not so bad looking girl. He turns to her and says, “You look like Princess Leia.” At that moment he goes right for it and they start making out. Hard. After a minute or so he pulls back and throws up. And, that was that.

14. The Fashion Insult

My beautiful divorced mother tends to get hit on a lot, and there are plenty of stories concerning these incidents, but the most awkward flirt goes to… She was at a wedding, and wearing a new shiny brown dress. Guy comes up to her, does what he assumes was a sexy face and says “Hey, what color is that dress?”

15. Painfully Awkward

I once tried to hit on a girl on a train. It went terribly.

She was sitting across from me and I thought I saw her smile at me. So I went and sat down next to her.

Me: “I saw you smile.”
Her: “What?”
Me: “I saw you smile at me.”
Her: “No.”
Me: “Hey, am I bothering you? Would you rather keep listening to your iPod?”
Her: “No, it’s fine.”
Me: “So, where are you going to? I’m on my way home from visiting my brother.”
Her: “I was visiting my boyfriend.”

(long awkward silence)

Me: “Oh shit, is this my stop?”

I ran over to the train door to make sure it wasn’t actually my stop, and then sat back down in my original seat and avoided looking at her for the rest of the ride.

I think the entire train car must have been watching me and thinking, “Wow, this guy is a complete idiot!”

16. Smooth Move Ex-Lax

I was in 7th or 8th grade and I was having lunch with my Dad when I saw this really cute girl about my age looking at me. I thought I was the shit back then and started glancing over at her. She notices and smiles at me and I smile back. I decided to go to the bathroom to do a walk by. I stand up and start my walk by. The whole time I am eyeing this girl. Suddenly, BAM!!!. I had been watching this girl and never noticed there was a low wall. I hit the and almost went head-over-heels. My Dad sees the whole thing and bust up laughing. I make the best recovery I can and run into the bathroom. After a few minutes of hiding in the bathroom, I hear the door open. My Dad comes in looks at me laughs and says smooth move ex-lax.

17. Who Doesn’t Like Gum?

In middle school the girl I obviously liked but was too much of a pussy to talk to got fed up, approached me, and struck up a conversation. After a few awkward sentences I had the brilliant idea of offering her some gum…because who doesn’t like gum? She thought I was implying she had bad breath and left.

Same girl like a year later asks me to dance at some party. I say “well, no one else is dancing” cause I didn’t want to look dumb in front of my friends as the only guy dancing…she thinks I don’t want to dance with her and leaves.

I was such an idiot back then.

18. The Rejected Liar

When I was in high school, before I could drive, I was waiting outside for my mom to pick me up after school. I was a junior, but recognized a sophomore that was known for getting with tons of girls. He walked up to this poor innocent freshman girl who was also waiting for a ride, and tried talking her up. She barely acknowledged him, giving him one word answers and then turning away. The kid KEEPS trying, for a solid fifteen minutes. The girl looked miserable until her ride finally came. Poor girl stands up to leave, and this kid goes in for a hug. She’s totally NOT having it, awkwardly escapes, and gets in the car.

The worst part was the next day, when I heard him telling all his guy friends about how he talked up this freshman girl and brought her back to his place for a bit.

19. The Man Who Couldn’t Take A Hint

I guess this sort of applies.

I used to be a “Check out Chick” at Woolworths in Sydney.

There were two customers in their late 20’s/early 30’s in my line who realized they went to the local school together. She was smoking hot. He was awkward/meek looking.

The conversation went something like this, soundtracked by the beeps of me scanning her items, so the guy was behind her in the line.

Boy: “Hey how are you? You still living around here?”
Girl: “Yeah yeah, I live just around the corner still, commuting to the city.”
Boy: “Wow, yeah yeah, that’s great. So do you still see random girl names from school anymore?”
Girl: “Yeah, I still see them at the pub and such.”
Boy: “So are you up to anything this weekend.”
Girl: “Nah, nothing on. Just a relaxing weekend actually, a weekend off.”
Boy: “Oh ok, cool. So would you like to hang out, go get some dinner this weekend then?”

Time freezes as everyone in the shop realises that everyone else in the shop was listening to their convo. It’s fucking tense.
The girl doesn’t know what to do. She stutters.

Girl: “Oh, ahhhh, thanks, but I’m actually really busy this weekend.”
Boy: “Oh Ok, but you just said…”

Mercifully, I had scanned all her shit and it was time for her to pay, so I interjected asking her for $30 or whatever the fuck it was. She rummaged in her purse and slapped down two $20’s and rushed out with her head down.

We all looked at the guy. He stayed looking down at the conveyer belt. I scanned his one item, disposable razors. He paid, then left. No words spoken. Rejected like a motherfucker.

The Grandma behind him in the line moved forwards and smiled at me.

Grandma: “That was awkward. Like a soap opera.”

20. Necrophiliac Undertakers

Some girl tried to tell me a joke about necrophiliac undertakers and pearl harbor day last weekend at a party and then when I laughed awkwardly, she attempted to plant a really nasty, wet kiss on me and missed.

21. The German Student

My cousin flirting with a german exchange student.

Still in high school and his opening line was “What classes are you taking”

She replies “Uhhh…. English, math, science, history… you know…. same as everyone.”

22. At The Movies

Back in first year, I took a girl I’d had a huge crush on to see a movie. Near the closing credits, I leaned in to kiss her, and she leapt out of the seat and screamed “NO!!!!” at the top of her lungs in the middle of the theatre. Driving her home was pretty awkward.

After that I had a lot more confidence asking girls out, because I figured “What’s the worst rejection that could happen? Scream in terror in front of more than a hundred people? Been there, done that.”

Dating and flirting got a lot easier after that.

23. The Dancing Machine

I once saw this guy wait for a girl’s friend to go to the toilet, leaving her alone, then he danced this really goofy dance (he put his arms out to the side with his elbows bent, then basically bobbed his arms up and down) all the way across the room to her, and – while still arm-bobbing – said, “hey……… wanna dance?”, to which she replied “No”, and he said “Okay”, then did the arm-bob dance all the way back across the room to where he started in 1 slick motion.

24. The Elevator

I was talking to a girl in the elevator of my faculty, I asked her name as I was raising my hand to make a finger gun gesture. The space was so small I ended up touching her tits with it.

25. God Bless You

When I was in college, I had long hair for [edit]being[/edit] a guy. I’m also a redhead (yes, no soul), so it was quite a mane. One brutally cold day, I was wearing a long black overcoat while pumping gas and I heard a voice behind me said “Hey baby, want to go back to my place to get warm?”. I turned around thinking it must have been directed at someone else, but instead saw the most surprised old man I’d ever seen. When he caught sight of my full beard, he jumped like he just touched a live wire. He stammered “ohh.. god bless you… ohh… god bless you… ” as he backpedaled back to his pickup truck, then ran over a curb trying to leave the gas station.

26. The Middle Man

Oh, man, once in 6th grade, I was sitting in class when I noticed the girl I had a massive crush on sticking her tongue out at me in a playful way from across the room. Well, I took this as an invitation to reciprocate. Back and forth, we traded silly faces. That moment may have been the greatest of my entire childhood had it not been followed by the worst. I felt a tap on my shoulder, and spun around to see the guy who made my life a living hell (tall, good-looking, captain of the basketball team, bullied me constantly) looking at me like I had just raped his dog. Apparently, she had been trading looks with him, and I was caught in the cross-fire. Yeah, that one still stings.

27. The Drama Queen

I had an uncontrollable crush on a gorgeous, tall unaffected guy named Alan my first semester of college. He lived on my floor and couldn’t be any less into me. I could tell that I had a snowball’s chance with him, but the hormones, they are impossible to ignore.

Being very inexperienced, I thought that creating drama would inspire him to see me as the cute vulnerable stereotype I thought all boys wanted. So I manufactured some reason to need to have a long, emotional talk in the hall and, with what I thought was superb timing, I looked up at him with big, teary eyes, paused for two heartbeats and then lunged at him for a kiss.

He called me on my shit so fast, my head spun. “I knew you were going to do that” he said. “You know I’m not interested in you. What made you think that was going to work?”

It was the first time I’d made a pass at a boy since moving to the city from the boonies and it was the first time I’d been rejected. He did me a favor in a way, though. I never used artifice or stereotypes or created false drama again.
I still wish he had let me kiss him, though.

28. The Sneeze That Ended The Evening

Sigh… I was flirting with a girl in a bar (and it seemed to be going well). About a half hour into our conversation, I had one of those very strong sneezes (the ones that come out of nowhere and cannot be stopped). I ended up snotting into my hand and had a string of goo from my hands to my face when I pulled my hands away.

I just walked away.

29. The Mysterious Rejection

I was once at a party in a dorm, heading for the toilet but still on the dance floor. This chick came to me and asked me if I wanna dance and I said “OK”. She looked at me confused and asked “What do you mean OK?” I replied: “Well.. yes”.
Then she says “no” and leaves.

I never understood what the hell happened over there.

30. The Burrito Discussion

I used to work at the mall, and many days we would go to a certain burrito place for lunch. None of us employees knew the cute hispanic girls who worked there (one guy just called them all “Maria” by default). There was one girl there I thought was especially cute, so I decided “By God, I’m going to ask her out!” So I went to the taqueria in question and, when she asked me what I wanted on my burrito, I asked for her number. Since that wasn’t a burrito topping, she paused, and then repeated the question. I looked around. There was a line of hungry, impatient people behind me. Staring, unamused. My momentum was gone. I mumbled something under my breath about “I’ve seen you here before” or some shit. Misinterpreting what I was asking her, she leaned over, pointed helpfully at one of the possible burrito toppings, and said “olives?” It was at that point that I realized that she did not speak English, beyond the basic vocabulary needed to make a burrito. I relented, and ate my lunch in defeat.

31. The Hippie

When I was 18 or 19, there was this cute hippie girl who I had an absolutely massive crush on. We’d been talking for a little while, and things were looking positive. So, myself and a group of folks went to meet her and her group of people in a park. Get there, everybody’s greeting one another, and her and I kind of drift together to do a little “greet with a hug” kind of thing.
Hippie girl. Wearing birkenstocks.

I step in to give her a hug, and kick her big toenail clean off. Completely off.

So yeah, she’s bleeding and in a lot of pain. I’m not sure what to do. 15 or 20 people are there gasping and commenting. Pretty awkward.