Cringe!: The All-Time Worst Attempts At Flirting

These advances are just genuinely bizarre.

Inept Pupil

"My friend in college started hanging out with 'pick up artists' and decided to demonstrate his prowess to us on the quad. His strat was to approach a girl and ask what she thought he should make for dinner that night (I guess it was supposed to lead to an invitation?) He then very-much-not-confidently approached a girl who was clearly in a hurry and, staring at the ground, delivered the line. The girl glared at him and, with great annoyance, said 'I have no idea! Spaghetti, or something?' And my buddy, still staring at the ground, said 'Oh-oh-ok. Uh, thanks' and shuffled away."

He also “learned” from this group that you’re supposed to touch a girl’s arm every time she laughs to condition her to associate your touch with a release of dopamine or endorphins or something. So I witnessed this several times as well, never done with any subtlety or charisma. He did finally get laid after about eight months of trying but the whole thing seemed creepy to me."

– Dr_broadnoodel

Weird Pitch

"It was me. In sixth grade I wrote a girl’s name on a rock and threw it at her during recess. Apparently they don’t like that 🤷🏻♂️"

– neon_eyeballs

"Did your approach change much from those days with the introduction of pokeballs?"

– OP

Stranger Danger

"On a walk with my dog, hot sweaty and not in the best clothes. This man drove behind me following me for a few minutes and I looked and said can I help you? He said let’s go on a date! Hop in!"

"I said no thanks and he revved his engine, asked if I was sure then sped off. I was legit scared."

– Allieora

These attempts at flirting are straight from a sitcom.

Down The Rabbit Hole

"A man asked a woman sitting next to me, 'I think your name is Alice since I'm lost in Wonderland.'"

– boukaree

"Oof. That made me cringe, imagining it."

– No_Letterhead_7683

Hairy Situation

"Guy on a trip saw a new girl in our group that he found cute. Decided to take the insult-as-a-form-of-flirting path and told her she had really hairy arms for a girl. Mind you, she had incredibly fair skin, so her hairs stood out more than usual. She, having too nice of a personality to say anything, laughed it off, covered her arm in a real smooth manner, and went on with whatever conversation was happening. My guy thought it worked because it 'made her laugh;' and you know you've got the green light when she laughs at your jokes. The next day he goes up to her during breakfast thinking he locked it up and exclaims, 'Oh my god your arms are so hairy that it's gonna make me sick!!' She doesn't laugh this time, runs back to her room, and changes into a long-sleeve shirt. She proceeded to wear long-sleeve shirts or sweaters for the remainder of the trip...in the middle of July. They didn't have a single interaction for the remaining 4 days."

– TYRONEmonies

Fumbling For Words

"My own. Drunk at a party talking to a cute girl she takes her glasses off. I thought this would be a good time for a genuine compliment. What my mouth said 'I like your face better with your glasses on' she just laughed. Pretty sure what I was trying to say is I like your glasses, and you have a pretty face. I just combined them."

– HooterEnthusiast

Clumsy Gymnast

"When I was in 3rd grade I had a crush on my babysitter."

"I decided to impress her by demonstrating my acrobatic prowess. I sprung from the side of a spiral slide and grabbed the monkey bars without touching the ground. Unfortunately, my hands slipped, I flipped through the air, and shattered my wrist in two places upon landing."

"My first thought was, 'Don't cry; be tough.' then I saw my wrist, it looked like a sine wave. I immediately started crying."

– ANerdCalledMike

Some guys come on way too strong

Hey, Barkeep!

"I saw two girls talking at a bar, and this guy walks up and interrupts them with a 'Heheheyyy, what are you ladies drinkin tonight eh? (Slaps the bar) Hey Barkeep, lemme get a couple rounds for these two!' They of course took the drinks, but promptly relocated away from that obnoxious dude."

– Xdude199

Bye, Scooter

"When I was younger I worked in a bar with a guy nicknamed 'Scooter.'"

"He'd say to any girl that was alone at the bar, 'Hi! My name is Scooter. I like to f'k. How do you like me so far?'"

"Some would glare and walk away, and a couple of times he got slapped across the face...but eventually he'd get a giggle."

"And he never went home alone."

– PJMurphy

Scene From A Gas Station

"When I was working at a gas station I had a dude just walk up to the register and just go ‘hey you have a boyfriend’"

"Of course he didn’t take ‘I’m not interested’ for an answer after. My assistant manager had to all put shove him out the door to get him to leave."

– SilverSoulFox

Daddy Cringey

"I worked in retail for a long time."

"I’ll never forget the time when this late 50s looking guy blatantly cat called an older woman who was wearing black boots. He said, 'Damn baby you gonna wear those boots all day for daddy?'. Then she goes, 'Not a chance.' He went quiet and she walked away. I had to hold in my laughter cause it was just so cringey to see."

– xSevusxBean4y

Either one's advances can come off as presumptuous and cocky or vulnerable and meek.

In most cases, people looking for love are overthinking it.

Here's a tip: Just relax and be yourself when approaching someone you like.

Being natural will not make you look desperate.

While there are no guarantees in scoring a date with this approach, chances are that with practice, you'll gain more confidence without overdoing it.