Women Are Sharing Their Cringiest ‘Nice Guy’ Stories And Holy Fedora (20 Stories)

u/TheAmericanWay1597 asked women on Reddit:

“Women of Reddit, what’s your cringy “nice guy” story?”

I knew the ladies would come out in SPADES but some of these are just truly atrocious and call to mind some of my own personal “oh f this guy” tales of dating. Which ones are the worst? Let me know in the comments.

1. Such a good guy

He wanted to impress upon me what a good guy he was, and he was also too scared to ask me out like a normal person. He killed two birds with one stone by having his “split personality” tell me it really wanted to kill me, but Nice Guy was bravely holding it back because he liked me so much. Obviously I fell head over heels immediately.


2. Fucking asshole

I was friends with a coworker. We had hung out a few times socially after work and got along well but it never really occurred to me to wonder if he was interested in me. At that point in my life I did not get a lot of male attention, and honestly was pretty cringey myself, but that’s for a different thread.

Anyway we were walking side by side and I guess he went to put his arm around me. It surprised me (like that ‘someone is tapping you on the opposite shoulder’ trick) and I turned abruptly. He took it as incredibly rude, gave me an angry lecture about leading people on and how disgusting you make someone feel when you literally flinch from their touch, and called me a bitch. Uh… sorry for my reflexes?

About a week later another friend came to me at work to let me know that guy was telling everyone I was a whore who was sleeping my way through the department. Nice!

The dumbest part was that I probably would have gone on a date with him if he’d asked–I just had no idea he was thinking along those lines. Bullet dodged!


3. High school

In high school a guy I barely knew tried to convince me to tell my parents that I was going to a friends house but really go hang out with him. I was normally rebellious but got the feeling that my parents would be right in telling me I couldn’t spend time with him. I politely rejected his offer and blamed my parents so it wouldn’t be awkward and he retaliated by covering my dad’s car in dyed tampons. Patrick, you’re a fucking creep.


4. See a pattern?

This all played out on social media, never met the guy in person. He found me through some posts I made on someone else’s discussion thread and tried to derail the conversation to how good I looked. A couple hours later, he messaged me. We go back and forth a little bit, him waxing poetic about how lovely I was and how he was looking to settle down and how every woman he’d been with (at least fifty) had shit on him in some way. I tried to be polite and let him down easy since he wasn’t what I was looking for at the time.

He quickly got pissed off and ranted about how it wasn’t fair and how fucked up it was that I wouldn’t at least give him A CHANCE, until I lost patience and blocked him. And that’s how I became #51.


5. 80 Emails???

I’ve seen two guys get into a fist fight at an office Christmas Party over who was going to ‘help’ an intoxicated 27 year old married woman get home…

I managed one of these guys and subsequently found out he had sent her 80 emails in one day with all that ‘why wont you talk to me’ ‘we’re friends’ etc stuff. He was fired but couldn’t see how he had done anything wrong.


6. Creeeeeeppyyyyy

Right after high school, a guy came out of the wood works and told me that he had a crush on me. I thought it was nice, but I just did not like him. He was always buying me presents and dropping them off at my mom’s house. I always said thanks, but told him I just wasn’t interested. We had the same group of friends so I would see him from time to time. When I would see him he would pull me aside and politely ask me to go on a date with him. I told him that I just didn’t see him that way. One day, I ran into him at the store and he asked me out again and I went on this long rant about how I was going off to college and I didn’t want to be tied down. He ended up asking me out AGAIN. I ended up walking away. He came up behind me and pushed me! He has this evil look in his eye, and I ran to my car and called my mom.

He ended up messaging me a couple days later and telling me that he’s just mad because God told him I was the one he was going to marry. I blocked him on all social media and my phone. He still managed to get my new address when I moved off to college and one time he drove almost an hour to my apartment. He knocked on my door and he handed me a bag of my favorite candy. I flipped out like I should have done many times before and I threatened to call the cops and get a restraining order. I’ve seen him once in the last 7 years with his wife and new baby. I hope he has changed!


7. Yikes

I met him at a party, gave him a ride home and after belting out “don’t stop believing” together, he asked for my number. We went on one date, and texted for a week. Then Saturday morning, I woke up to 50+ texts that started with asking what I was doing (sleeping because i worked in the morning) and went all the way up to “I should just kill myself since no one wants to talk to me”

I told him that was unacceptable as I had already told him i worked saturday morning, but even if I hadn’t theres no reason to text me over 50 times. If I’m not answering, I’m not answering.

He whined about being so nice, and how good he was to me and blah blah blah blah blah. Thankfully, when my friends asked why i was ignoring such a nice guy, showing them the texts was enough for them to drop it.


8. Stood him up

This guy messaged me on OkCupid. He was 62. Not necessarily a deal breaker… except I was 20 and he was a dozen years older than my parents. I said thanks but no thanks, I was uncomfortable with that much of an age difference, good luck out there.

He flipped. Nonstop messages vacillating between how I would regret this, wheedling, compliments and apologies, and call me a whore, a slut, a blueballer, etc. Literally dozens upon dozens of messages a day. He was a lawyer! He had ways of making me regret this! I would never do as good as him! No other man would treat me so well and I’m a whore if I say no! On and on. (This was many years ago. At the time, you could report someone for harassment on OkCupid but it didn’t stop that person from messaging you.)

Finally, I told him I would meet him in the city, at a popular college bookstore, at 2pm. Wouldn’t you know it, I somehow ‘forgot’ to go. After another day or two of berating for standing him up, he got the hint and disappeared.


9. Rapist

I used to work at Gamestop and the building was connected to a Starbucks. He recognized me from high school, but was a year under me, so I had no idea who he was (I generally kept to myself). He’d talk to me as I waited for my order and he seemed pretty cool.

A couple weeks later he tells me I’m pretty and if we could hang out. I’m engaged, so I told him outright. He promised me that he just wanted to be friends, and I’m – apparently – a very gullible person. He’d get me free Starbucks, tell me I’m a great artist, yada yada. About 2 weeks later he asks me to meet him at a bar because he’s upset about something. Trying to be a good friend, I go to comfort him.

So, I go to the bar, and he’s already drunk. I didnt drink because if things turned sour, I could just leave. He gets all feely on my thigh. I tell him I’m uncomfortable, so he stops apologizes that he’s drunk. I kick his ass at pool and he asks me to go smoke with him. I dont smoke cigarettes, but sure I’ll go talk.

He pushed me against the wall, kissed me, and put his hand in my pants. I fought him back, but a dude leaving the bar got him off of me.

No “nice guy” will ever be trusted again.


10. Uh, what the hell, dude?

There was a customer who came into the coffee shop where I worked. I asked him what he wanted to drink and he moaned, “Something that will fix a broken heart…”

I forced a smile while he told me that he had been stood up… again. I smiled through all of it and when he still hadn’t told me what he was going to order, I suggested what I like to drink. He asked what it would cost, and I said, “No charge. Tomorrow’s another day.”

I made his order and went back to finish washing dishes.

He came back in and brought me a Cosmo magazine, saying he was a magazine vendor and he thought I might like it and thanks for being nice. I said no problem, wished him a good night and forgot about him.

A few days later, my co-worker races to the back to tell me this guy was back and blocking our drive thru. Now, when he came in last time, I had my wedding ring on a necklace because I didn’t like to wear it when I was washing dishes. I asked her what he wanted and she said he was demanding to talk to me.

I said, “Tell him I’m not here.”

She says, “He saw your car.”

OKAY THAT IS CREEPY. He knew what I was driving?

I reluctantly come out after popping my wedding ring on my finger. The guy has a large bundle of carnations and a box of chocolate and is in one of those big old 1970s vans with the little circle window on the back row.

I made sure my ring was very visible and made sure to fiddle with it. I came up to the window and asked how I could help, and he saw my ring. His face reddened and his tone became very threatening.

“Where did you get that ring?”

“This ring? My husband gave it to me on our wedding day seven years ago.”

He is pissed. He begins to bellow at me.


“I was, you just didn’t see–“


He threw the carnations at the window as we pulled it shut in a panic. He beat on his steering wheel and honked the horn and yelled profanities. We were about to call the police and were locking the cafe doors when he squealed out of the drive thru, almost knocking the patio furniture over.

Yeah. He was a super nice guy.


11. Leading him …on?

Some guy messaged me online and seemed nice enough. Asked if I’d like to meet up with him. I said sure. He tells me a Starbucks between our places and said he’d see me in 30 min. I was like, “woah, not right now, it’s 10pm” He said okay, but he’d like to keep talking to me if it was alright. Few days later this exchange happens over messenger: Him: “hey what’s up?” Me: nm, how are you Him: I’m good. Me: good 🙂 5 min pass so I assume he was busy for a sec Him: Well if you don’t have anything to say you fucking bitch, don’t lead me on and let me think that we can be together. You’re nothing but a fucking whore anyways. Only whores lead nice guys like me on. Fuck you fuck you you fucking whore.


12. What in the world?

Met up with a guy from collegeclub.com and we had planned for a quick bite to eat. I had forgotten my wallet so he came to my dorm room with me to quickly grab it. We get there and He immediately starts looking around at all my of photos etc. around the room. He finds my Homer Simpson slippers and a rooster beanie boo my nephew had left there. He takes the rooster and stuffs it in Homer’s mouth and makes it move (as if the slipper was chewing) and says “Look at me. I am vain. I create suffering for animals so I can feast. Selfish hungry bitch”. I was speechless but then he opens my drawer and starts throwing makeup around saying “this is tested on animals – I am vain. Animals suffer for my beauty” And THEN opened my wardrobe and started throwing clothes around saying “these things have been made in sweat shops” My friend called security on him.


13. Manager banned him

I once (about 9 years ago, when I worked in a liquor store) had an older customer that would come in, and (I thought) play flirt with me.

A lot of customers play flirted with me, so I didn’t think anything of it. Plus, this guy was, like, twice my age….and I was no spring chicken. I had no idea that he seriously thought we were really flirting.

Until one day…

…he asked me out. Not in a regular way, mind you…oh, no. He said, “So, we’ve known each other for a while, now….I’ll just wait until you’re off tonight, and then we can go out. I’ll take you to (expensive restaurant)!”

I politely declined.

He went ballistic!

Long story short, the manager banned him from the store for life.


14. *Owed him my body*, he says

I lost a bunch of weight and my ex from high school contacted me out of the blue. He pretended he wanted to catch up and claimed that he was in a committed relationship so I let him visit me. I was very naive. Long story short, we had non-consensual sex and he outright said that the reason he contacted me was that I owed him my body because he suffered so much embarrassment having to date me while I was fat.


15. Sure, sure, just don’t UNDERSTAND you

He was a nice guy but had his friends stalk me in an online mmo after I was late texting him back. He was also super passive agressive like “I see you online, but you aren’t responding to MY messages.”

The straw that broke the camel’s back was when he showed up at my college campus, which was an hour from where he lived, and wanted to randomly hang out. But [he said] he wasn’t a creepy stalker, he was just a nice guy I didn’t understand.


16. Friends like that…

I’m a girl, but this story is about my husband and how he caught the bad end of a “nice” guy.

A few years before I met my husband, he decided to go to a party. He gets there and some random girl walks up to him, says “Your cute” and kisses him. This amused him, so he started chatting with her. While chatting, he notices a very angry, short man standing next to her. The man is scowling at my husband and it’s making him uncomfortable. He can tell the guy is pissed at the attention girl is giving him, and it’s just not worth it, so he stops talking to random girl, turns away, and starts walking to another room. It’s at this point husband feels short man punch him in the back. When he turns around, short man is running away and actually runs out of the house and never returns to the party. Husband laughs it off, cause it wasn’t even a hard punch. But then somebody notices husband is bleeding, and there is a hole in his shirt. The short fucker hadn’t punched him, he stabbed him.

Random girl saw this all go down and was pretty mortified. Turns out the short dude was obsessed with her, they were “best friends”, and he accompanied her everywhere.

The knife was pretty small, so it didn’t do any real damage. But he still has the scar.


17. I report all these assholes

I was on a dating website but hadn’t logged in in a little bit. When I did I found two messages from the same guy. The first one was telling me that he thought my profile was great, he had a dog and loved hiking. Okay, cool, I enjoy those things. The second one came two days later saying how “I guess you don’t want something real, bitch”. His first message was actually decent so if it wasn’t for his crazy nice guy follow up I might have given him a chance.


18. Made it up

The one that was the most upsetting was a guy who had been my friend for years, who I was close to and confided in, telling me my boyfriend at the time had cheated on me. I wanted to confront the boyfriend and this “friend” kept dissuading me, telling me to just drop contact with him, and trying to comfort me with physical contact.

Obviously I still confronted my boyfriend. He said no such thing happened. And it turned out my friend had made it all up.


19. Uh, okay.

A guy at a bar bought me a drink (even though I really tried to not accept it), and he asked me if I was single. I told him that I was dating someone and he took the drink back and called me an “ugly whore.” Uh… okay… haha


20. Oh no, a fedora

I was sitting at the bar by myself and this guy in a fedora comes up to me and we just start talking. He seems okay, we got into some casual conversation, then he starts talking about how he thinks girls should be nice to him if he does something nice for them. i.e. open the door for them or buy them a drink.
I tried for a sold half hour to get him to understand that a girl was not going to fall head over heels for someone who thought that opening the door for them meant that they were a knight in shining armor. I tried very hard but he just would keep talking over me.