Random Most Cringeworthy 'Nice Guy' Stories (16 items)

• (#10) He Tried To Pick Me Up At A Funeral

  From Redditor /u/summersintheair:

  When I was 17, one of my most favorite people in the world passed away very unexpectedly. After the funeral we had a wake at the pub, then family came back to our house... My cousin brought his girlfriend - who we knew and liked - and another friend who we'd never met before.

  I'd spent the day crying constantly (and I'm not a pretty crier) and at some point, [my] cousin's girlfriend came up to me, giggling, and said "our friend really likes you." I said I wasn't interested and after the usual comments "oh but he's so lovely! But he REALLY likes you!" she went away.

  After a half hour she came back and said "He's outside crying because you rejected him. He really wants you to go out there and cheer him up." I got my uncle to go out there and tell him to bugger off.
• (#3) Good Guy Gone Bad

  From Redditor /u/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 2 am repeatedly until I answered and told him it's too late to talk. After about the third 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.
• (#9) He Changed His Mind About Not Liking Me When I Started Dating Someone Else

  From Redditor /u/soggybutter:

  I had a crush on a dude in high school, he was part of my BFFs circle so we were together a lot. I'm up-front so I was pretty clear that I had some feelings for him, but he was uninterested in being anything more than friends. Whatever, I had another boy kinda chasing me so I gave him a shot and we start dating, and I kept the friendship with the Nice Guy.

  Flash forward a year, Nice Guy has become one of my closest friends. We eat lunch together, hang out like everyday, and my boyfriend is often included, although they weren't close at all.

  Then a week before Nice Guy leaves for college, he confesses that he's totally in love with me, my boyfriend will never fully understand me or treat me right (it's been 4 years and we are still together soooo), and I pretty much owe it to him to dump my bf and f*ck him before he moves to school.

  I said no, obviously. He freaks out and tries to make me pay him back for all the money he spent on me, which I had never liked in the first place and was always done sneakily, like putting movie tickets on his card before we got to the theater or paying for our food when I was in the bathroom.

  He spends like 3 weeks messaging me just really mean, vile sh*t all the time, including some deeply personal stuff he was aware of due to our friendship. It hurts a lot to really regard somebody as a good, close friend and then be dropped like a hot potato when he realizes you still won't put out. He still messages me occasionally, usually to try to hit on me and get pissed that I still love my boyfriend, and then complains about being single. Gee motherf*cker, I wonder why?
• (#15) A Guy My Grandfather's Age Held The Bus For Me... So I Would Kiss Him

  From Redditor /u/Tsunoba:

  There was this guy last year that got on the westbound bus a little after I did, and then we got off at the same stop and waited together for the northbound bus.

  He was nice. He was friendly. He took an interest in the classes I was taking. I kinda viewed him as this kind of grandfatherly type of man, since he was in his 60s or 70s. I'm in my late twenties, for reference.

  One night, I had to go to the store that's right by that bus stop we waited together at. I got stuck behind someone who took a while in line, so I was rushing to make the bus (because even though it's a "Time Point," where they're supposed to stop and wait if they're ahead of schedule, some of the drivers don't).

  I'm running up, and the driver did actually wait like he was supposed to. He was taking a smoke break out by the stop, and said, "Don't worry, the old guy let me know you were coming."

  Awesome, super nice, right? I go in, old guy says pretty much the same thing: He let the driver know I'd be out shortly, and the driver decided to take a smoke break while they waited.

  Then the old guy passed me a note, told me to read it when I got home.

  It said, "Does that deserve a kiss someday?"

  I know that's not the worst thing in the world, but...

  I started taking a later bus. It meant I didn't get home until about 9, but I didn't have to deal with him anymore.
• (#6) Dated A 'Nice Guy' For Five Months To Find Out He Thought We Were Just Friends With Benefits

  From Redditor /u/Eshlau:

  We met in a group in undergrad, became friends. Slowly we became closer, I developed a crush on him, [we] started hanging out more on our own, and one night after some drinks it escalated to kissing/cuddling.

  I messaged him later letting him know that while I enjoyed what happened, I didn't think it was a good idea for us to keep it up, as I had feelings for him, and wasn't interested in a friends with benefits kind of setup.

  He told me that he kind of had feelings as well, and that it might be nice to see how a relationship developed. So we did. We start dating - dinners, movies, all the physical stuff that comes with a relationship. When he was briefly hospitalized, I spent every night there with him.

  I opened up to him over time, and told him about my history of sexual abuse, family history of substance abuse, etc. He opened up about his history of being used by his exes, how they were all horrible and had treated him horribly, how he's just always been so nice that everyone takes advantage of him, that all he wants is to find a nice girl who will love him for who he is and that he can treat like a princess.

  One night (probably about 4-5 months in) we're laying in bed together watching a movie and I started telling him about a funny conversation I had at work, "So then I was saying, my boyfriend..." and I feel him stiffen up, and he kind of awkwardly says, "You know we're not dating, right? Like, I thought we just had a fun thing going..."

  So, apparently we're FWB. The exact thing I told him I didn't want. I asked him if we could start dating then, and he said he was just too busy for a relationship (even though we were basically in one), blah blah. I told him I was hurt and felt used, and that I wasn't interested in being anything more than acquaintances in the future.

  After that, I slowly started seeing someone, a guy who was actually pretty great and had actively pursued me, and guy #1 FLIPPED OUT. Apparently, even though he didn't want to be in a relationship with me, I wasn't allowed to be with anyone else.

  For months afterward, he spent most of his time badmouthing me to whomever would listen, talking about how I used him, how I'm just like every other sl*t who thinks she's too good for everyone, how he had treated me so well and I had ripped his heart out.

  The worst part, though, was that he told numerous individuals and groups of people all about my personal history. Apparently, a couple of times, after a couple drinks, he would even start to cast doubt on it, comparing what I "did to him" to my past abuse, stating that it was surprising to him that an alleged [abuse] victim would "r*pe" the feelings of innocent men. We no longer speak, but I still hear about things he's said about me a couple times a year.

  It really made me wonder about all those "terrible" exes he had, and made me put more faith than ever into the thought that the way people talk to you about others is the same way they'll talk to others about you. What a nice guy.
• (#12) He Spent Two Hours Explaining How He Manipulated Me (And Nine Other Women) Into Going Out With Him

  From Redditor /u/midnighteyesx:

  I was on OkCupid for two years and had over a hundred messages and about 30 dates, two of which became relationships, one of them I am still currently in.

  It was a dry month, mostly one liner messages asking me "how many fingers do you use when you masturbate" or "u seem cool I wanna talk more dtf" and then one guy, Alex* asks me about my degree, and how he [too was] pursuing higher education and working on a thesis. That got the ball rolling so we had very nice conversation for days where each of us would respond to the message, make a few comments, maybe tell a story, and then ask another question or two. Honestly the best conversationalist I'd come across. We agreed to meet at a Starbucks.

  I get there, order, pay, and sit down. He arrives a little late, has to wait on line, and we sort of steal glances every once in a while as he waits.

  Then once he sat down, we said how nice it was to finally meet, he says "next time I'll give you a different time to come so I can be here to buy your drink." And I said, "that's very nice of you but it's no problem, you don't have to buy me anything." To which he turned his whole body to face me, put his elbows on the table and said, "Thank you. Thank you. You know that's a great outlook on life and that's something I'm really looking for in a woman because you know I dated this girl who I met... at some macaron place and you know what they charge for macarons these days? Three dollars. Three. So I order two and she orders three and a drink and I took out my wallet and was a dollar short so I asked if she'd cover that and would you believe she did not have a dime on her?"

  Then a few moments later we talk about OkCupid (macaron girl was also off OKC) and our weirdest dates and most random messages, and this was the moment. 

  He said: "You know I've had 9 dates in two weeks from my new method. Get ready because I'm about to explain to you the method for getting you girls in the chair. It starts with messaging. You always respond to a specific, add a story, and then ask a question. In that order. Then you say you'll meet somewhere for something quick like a drink or a cafe. Then you drop the bomb that you're the total package, you're the man, you're in the zone, and they can't do anything but agree because it worked. It totally worked I mean, here you are in the chair, and here I am on date 10."

  Then for the next two hours, explained to me just how great he was at getting women in the chair, but had no desire to be in a relationship, he was just a serial dater because it would be too much work, and that he was too considerate of the woman who he would be leading on with hopes of being official or growing past dates and open hookups.

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