Wait, They Actually Tried That?! 71 Men Flirting So Bad It’s Hilarious And Horrifying
Alright, buckle up! Today we're diving into some of the wildest, cringiest, and downright creepy ways men have tried to flirt with women. Spoiler: some of these moves are so bad, you'll wonder how they even got past hello. Let’s jump right into the madness!
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Wearing a backless dress, my bra peeked out and this guy actually pulled on it at a club. When I turned to slap him, he grabbed my hand and said, 'I love women who fight back. Want a drink?' Uh, no thanks. I kneed him and bolted.
Leaving work late after bartending, I got followed and cornered way too many times—even digging through the trash doesn’t keep creeps away. Spoiler: age, clothes, and time of day don’t matter to these predators.
At 15, a 42-year-old and his mom tried to pressure me to go home with them. Later at 19, a guy said he wanted to break into my house and hide under my bed. When I refused, he threw a tantrum. Weird much?
Some guy kept telling me I was pretty and asked if I went to high school. I said I'm 27. Surprise! He lost interest. He was clearly 40+. Gross alert!
A guy asked if I was 18, then knocked on my mom's door to ask permission to date me—while I was still in high school. Mom shut that down fast, but dude screamed, 'I’m just being polite!' Nope!
At 12, some boy sent a letter to my dad asking to be betrothed to me, promising to keep me away from sin and make little soldiers. My dad laughed so hard he still teases me about my 'future husband.'
After finishing work, a maintenance man hung around my basement and popped the question. Another one? Two cops pulled me over while walking my dog, exchanged numbers, then pressured me for feet pics. I reported 'em!
Some guy tapped a lady in a wheelchair and said, 'I can roll you anywhere, and you can't do anything.' Turns out, flattering wasn’t on the menu.
Driving home at 3am, a cop pulls me over, chats casually, then starts asking out of the blue if I want to date him. Things got pushy, so I scared him off with a fake cop friend. Phew!
Walking and a car pulls up, dude says I’m cute and wants my number. Spoiler: it’s not cute, it’s creeeeepy. No one needs a stranger tailing them in a car. Just no.
Guy flirts at work, I’m shy and give him my number. I don’t respond much. He stalks me, his cousin too, shouting ‘Wifey!’ across the yard. My mom stepped in and threatened cops. Finally, peace!
Maintenance guy was fixing stuff, leaves, then casually mentions rifling through my underwear drawer. Yeah, that happened. Then he asked me out. I was 15. He was maintenance MAN. No thanks!
Worked at Wendy's, dude comes in all cash, grabs my hand during change with intense eye contact. Years later, I match with a guy on a dating app, turns out it’s HIM. I blocked faster than lightning.
A coworker hid a young woman’s phone, offered his to call it, then bam—he's got her number. She was a third his age. Yikes on top of yikes.
This officer showed up at my house after following me home. Tried my door while I showered. Then came to my workplace asking me to wait tables for him. Banned by two police agencies soon after. Good riddance!
Working customer service, the married stepfather of my teen coworker tried chatting me up and dropped a ‘you're so hot’ before walking off. I was 19; he was definitely in his 40s. Ew!
Guy asked if he could cut a piece of my hair to keep forever. Another told me I looked so delicious he wanted to bite me — then pulled out dentures and started gnawing gums. Next!
At 15, while painting on a ladder, a guy working there snuck behind me and grabbed stuff he definitely shouldn’t have. Nope, nope, nope.
At 18, at a bar with my dad, some dude comes over and asks if my dad is my boyfriend. Once he found out my dad wasn’t, he asked him for permission to take me out – saying he’d bring my dad a beer. This man was definitely at least 30. I left, fast.
Stayed at a hotel for weeks, chatted with one guy, then a DIFFERENT night worker I didn’t know calls my room at midnight asking me on a date. How did he even know who I am or where I was?! Super creepy.
A plumber had my landlord call me to ask out! Mind you, he was 20 years older. Landlord said he was great, but I said, no thanks, that’s just inappropriate.
Working at Sam’s Club, I demoed cheese and a guy around 40-60 asked, 'If I buy all this, do you come with it?' I was 23 with a baby face. Another guy awkwardly tried chatting me up, stumbling when I said I had a girlfriend. Savage.
At 19, I babysat for a family who referred me to another. A man called, asked my age, then told me I could make money 'on my knees.' Mortified then, still gross now.
At the hospital, while helping a patient fill paperwork, her dad came up and asked me out—right in front of his daughter. Awkward penguin moment.
In Paris alone, guy stared at me on the metro, changed seats when I did, followed me through trains and nighttime streets. When I yelled, he said, 'Madame, you attract me.' Heart still racing.
At 16, working cashier, ice delivery dude flirted while on the job. After leaving, he called the grocery store asking when I got a break. His low voice said, 'You know why.' I hung up. Boss saw him waiting outside. Creepy alert!
At a Halloween party, a friend’s high school son’s friend kept pestering me for my number at 14. I was shy, didn’t push back, but the host’s son decked him, yelling 'She’s 14!' Then the creepy dude was kicked out. Good move, host.
Regular at grocery store always bought rubbing alcohol (wink, vodka). Asked me out, got mad when I said no and called me a stuck-up. Card declined. Then promised to buy me shoes if I said yes. Bro, you were declined on $3!
A county sheriff recognized me from work and asked me out while I waited for my divorce to finalize. I didn’t even look at him. My lawyer however stepped in, asked for badge number, and told him to find another target.
Worked night shift at a liquor store. A man threatened to kidnap me and followed me to my apartment. This isn’t persistence, this is nightmare fuel.
Bartender stalked by neighbor who told everyone he’d wife me up. His cousin too. He followed me, messaged non-stop, and even pestered my friends. Only stopped after relocating. A 3-year saga of obsession.

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