Culture Women Of Reddit Describe Their Most Cringeworthy "Nice Guy" Stories  

Brandon Michaels
75.9k votes 13.9k voters 431.4k views 16 items

List Rules Vote up the most embarrassing real-life tales of so-called "nice guys."

In a world where our next date is just a finger-swipe away, you're bound to have your fair share of duds. For women, sometimes the only thing worse than sleezy pervs who immediately ask for nudes are the cringeworthy "nice guy" encounters. 

This is when you are approached and/or befriended by a guy who seems, on the surface, to be a genuinely nice guy, but really isn't. Sometimes it's a guy you just met who helps you down the stairs when you're injured, and then he throws your crutches on the ground in disgust when you don't want to go on a date with him. Sometimes it's a guy you've known for so long, you're certain he's a "nice guy," and then he waits for his girlfriend to leave the room to try to convince you to make babies with him. Either way, you are left wishing you had never met such a "nice guy."

If you have your own gross "nice guy" stories, or just want to know how to avoid becoming someone else's, check out this list, where women of Reddit share "nice guy" tales of their most cringeworthy encounters.

1 7,810 VOTES

A Cross-Dressing Regular At My Shop Told Me I Was Making Him Hard


From eleveneleventimes:

"I own a small vintage clothing store. I have a regular cross-dressing old man who comes in looking like Linda Richman and smelling like grandma if grandma was a whore. Well, he was very sweet at first but then started coming in and saying semi-perverted things. Then one day he came in and we were having a casual conversation and he interrupted me with this.. "standing here talking to you and looking at you is making me hard. It feels like I might cum in my skirt any second." NICE."

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2 6,793 VOTES

Good Guy Gone Bad


From Refinnej808:

"Met a guy in high school who was really nice. We would talk and hang out at lunch. One day, he called my house at 2am repeatedly until I answered and told him it's too late to talk. After about the 3rd time he called again and my sister (my guardian at the time) answered and told him to stop calling. He called her a b*tch and he stopped calling.

The next day at school I avoided him and he followed me around. I made sure to be around someone at all times and he would harass another guy and say "why are you trying to steal my girl?"

Then when I was sitting at my desk he sat on the ground by my feet and kept trying to slide his hands up under my clothes. After about a week of this he finally left me alone."

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3 6,588 VOTES

He Drugged My Drink So He Could Be My Hero


From sweetrhymepurereason:

"I once was out with friends and my drink was spiked. One dude stayed with me to take care of me and my other friends left because we all knew him. Turns out he spiked my drink himself so he could 'save me' and show me how caring he was.

He told a mutual friend thinking that the guy would think it was a cool move. Our friend did not think it was cool, and told me what happened.

This dude also laced the one-hitter we were using with something that same night. I could have died, but he really thought he was being a genius pick up artist. The worst part is that we had actually been talking for a week or so before this - I clearly already liked him, and he still felt the need to do this.

Keep your eyes on your drink and trust your instincts."

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4 6,628 VOTES

He Gave Me Such A Horrible Double Wedgie That I Bled


From SheWhoComesFirst:

"A guy friend in junior high. We had several classes and sat next to each other, platonic, loyal friends for 2 years before he got weird. He was hilarious, we could talk about anything. His house had a pool, so during warm weather a bunch of us would swim at his house after school.

One day he invites me over to swim after school, when I get there, no one else is there, which was weird. He was splashing me, sort of aggressively flirting, dunking me, so I get out of the pool and he pins me down to kiss me. So I play it off as joking and leave.

I give him the cold shoulder after that and he was pissed.

Two weeks later and at a different friends' house he and I are both there for a swim-birthday party and he and another guy give me a simultaneous front and back "seesaw" which is like a horrbile double-wedgie in the pool. My swimsuit cut me so badly I bled."

6,156 472
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