20 Women Reflect On Their Creepiest Date With A “Nice Guy”

A tale as old as time is that women have been attracted to bad boys forever. It usually doesn’t end well, however, leading to heartbreak and pain. But what if a woman chose to give the nice guy a try instead. Would that lead to a happily ever after instead?

#1

Image source: the-lizard-effect, Nadia Dulina/unsplash

Went out with this guy a couple days ago. It was polite but we didn’t have chemistry at all. He was super friendly and fun so decided to still see where things could go. Went to his place to watch some tv and talk. It was fun so decided I’d agree to a second date if asked. Started to get late and I was getting tired so I told him I was heading home. He flipped out.
Blocked my way to the door ”Didn’t you have fun?” ”What’s wrong” He insisted I aswered his questions and the fact that I was tired wasn’t cutting it. He got more mad and pushed me against the door. After the push I got out of there and he let me leave. Blocked him everywhere and now I have bruises on my arm to remind me of the incident.

#2

Image source: Sta_Ja84F, Sodbayar Photography/unsplash

The date wasn’t too bad, although he kept changing pretty much every single sentence he said so it would fit my interest. Something like “I like ice cream” “Cool, I like frozen yoghurt” “oh yeah, that’s what I meant. Ice cream is nice but frozen yoghurt is amazing” and so on for 4 hours straight. At the end I had no idea what he was actually like.
He also kissed me in the most awkward way possible. I guess he thought it was going to be romantic and spontaneous but it wasn’t. Then kissed me again when he walked me to the train station. He hugged me so hard I couldn’t breath and started making weird noises (kind of like what some people do during heavy, pre s*x make out sessions, except it was a rather quick kiss in a public place).
Started texting me before I even got home and when I didn’t answer, got upset. Told him he was nice but I don’t think we’d work out. Said its cool, asked if we can stay friends. Silly me, I said yes.
We kept talking for about a month, during which he very “friendly” kept checking if I had slept with someone else and making sure I know how much of a s*x god he is (“you know, I once even made my lesbian friend c*m super hard”). This is also the time I met my current BF and was meeting a bunch of new people at uni, so we’d talk less and less each week.
Then one day he asked me out. I said I wasn’t sure if he was completely fine with us being just friends so that wouldn’t be appropriate. He went on this massive rant about how he’d actually been seeing someone else in that time, but they broke up shortly before that, how he’s so over me and didn’t even think I’m that hot anymore and how nothing would happen. I said no, because I was broke and couldn’t fully enjoy myself while worrying about not spending too much (we were supposed to go to a Metallica concert, apparently his best friend had spent £120 on his ticket but then last minute found something better to do…) but he promised he’d take care of everything and we could chill at his place with pizza and some films, as friends. I said I could consider the concert but there’s no way I’d stay over. I mentioned texting someone else to see if they would be fine with me sleeping over at theirs afterwards. He jokingly asked if it’s someone I’m sleeping with and I said it’s none of his business. Then he told me how much of a b***h I was for sleeping with other people and not sleeping with him, said it’s so unfair that he knew me so much better but he felt like other people had more rights to me than him and that we kissed and he didn’t expect me to be this slutty (btw, I did not want to kiss him, it was just so random I felt him making out with me before I even realised what his intentions were and stopped it rather quickly). The he called me a few more names, said he’s such a nice guy and didn’t deserve to be treated like that and we never spoke again.
Fun times.

#3

Image source: randomised99864, Gabriel Ponton/unsplash

Throwaway account for this as don’t want my story tracing back to me.
I met him through online dating and after a couple of weeks of chatting online decided to cool things off as he was giving off a creepy, needy vibe that frightened me. He would ask about ex boyfriends frequently and tell me that he would be good for me, ask sexual questions without any encouragement and want to know intimate details. I forgot all about him until he sent me a random message months later and apologised for his previous behaviour which he blamed on a tricky break up.

Time passed and he seemed a new person so I gave in and met with him. Our first couple of dates seemed fine with just a few odd comments that I should have paid attention to. Then he started questioning where I was and who I was with, but again I just foolishly ignored this. The first time (and last time) I stayed at his we went out for a drink beforehand and he was judging me for having a couple of beers. When we got back to his I wasn’t feeling up to anything sexual so told him firmly no and went to sleep. Later that night I woke up to him on top of me.

I never confronted him about this. I just pretended i hadn’t woke up and made my excuses the next day before blocking him from by life. I’ve never told anyone this before. I just wish I’d listened to my previous instinct and keot well away.

#4

Image source: tooscaredtospeakup, Victoria Romulo/unsplash

Nice guy story where I was the nice guy. To this day I feel terrible for my actions. This started 12 years ago when I was 19 years old.

Met a girl at a club, hit it off right away and she ended up being my girlfriend. At the start everything was fantastic, we were genuinely happy together and I was in a constant state of not believing my luck of having found a girl as awesome as her.

About one month in, I did something very stupid. I met another girl, we had drinks and ended up sleeping together. Instead of coming clean with awesome girl nr1 I decided to keep it to myself. All was fine, except for a little lingering voice which said that if I could do such a thing, surely she could as well.

This voice grew louder over time. I started joking about her seeing other guys, you know those half-jokes which arent funny at all and mainly make the other person feel bad. I started checking her phone, reading her socials etc. At some point I was certain she was cheating on me, eventhough there were no signs of it whatsoever. I started cutting her off from her friends (especially male friends) and getting angry if she did not respond to my texts inquiring where she was, with who and why she was not home. I started doing surprise visits and getting really angry with her if there happened to be male friends in in her vicinity, even if they were in big groups. My reasoning with her was always that what we had was special and that she shouldnt want to spend her time with anyone else than just us. Manipulative as I was, I’d change tactics in the span of minutes, being real nice and friendly one moment only to catch her off guard and get furious an instant later. I’d use my kindness to get information, trapping her in a constant cycle of guilt.

Fast forward a bit, we’ve been together for a year now and she has gone to uni making new friends. We are fighting every day now. One time I leave her house after a fight and realize I forgot my phone. I go back in (i hade her keys) and found her crying in her room. A moment of clarity struck and I broke up with her, justifying it to myself as a messiah act.

Surely this would have been the end of it, but nope. What followed was 3 years of me texting her, calling her, trying to figure out if she was seeing anyone and getting real angry when she was. It just did not stop. Even if we did not meet up for a few months and I had somehow convinced her I had changed, I’d end up doing the same thing over again on the very same day that we met up. As in, surely if she saw how nice I was now she should want me back. So why doesn’t she? Insert guilt trip etc. This went on for years and it k****d me. I saw what I was doing to her and felt horrible for it. But that voice and entitlement kept popping up so every time she offered me friendship, I’d unleash the guilt trip.

At some point it stopped. I started analyzing my own actions in this and shut off all contact with her or anyone of her friends (which were also my friends). I just forced it all away and every time I felt this voice popping up, I’d try to analyze where this entitlement was coming from so that I could fight it. I can’t really explain how it ended up going away, other than the fact that one day I noticed I did not feel these things anymore.

For a long time I refused any form of romance with anyone, afraid that I would start the cycle again. After some time I did meet someone else, we’ve been very happily together for seven years now. When we started dating I was very open about all this, which I think helped a lot. I rarely feel these pangs of jealousy pop up anymore. When they do, I know they are not rational and I can shrug it off with ease now. Its something that won’t ever fully go away but I know it’s all me and I know where to find help when needed.

I wanted to share this here not for sympathy or whatever, maybe just to show how creepy the mind can act from a first person perspective. I feel terrible for what I have done to another person, nobody is entitled to another person’s love, attention or affection.

To those who are currently in a situation like this on the receiving end: walk away, cease contact, break it off. People don’t change overnight. Even after years it can still linger on, buried deep in the mind. And ultimately it’s personal responsibility to face your demons and do something about it, don’t get guilted into becoming the pillar of stability for another person to hang on to. The best thing you can do for the both of you is walk away.

#5

Image source: fuqmook, Eduardo Ramos/unsplash

We were friends in high school and most of college. It was one of those things where he was a friend of a friend, but we always went to the same parties, hung together in the same group and so on.

The guys in the group would always say things like, “Ah man you and Kyle would be so great together! You should give him a shot!” I’d kind of laugh it off because for a majority of the time I had a boyfriend.

Eventually me and the boyfriend broke up, and about a week later Kyle asked me out. I wasn’t really ready, but I figured it was a first date and everyone had been pressuring me into giving this guy a chance so I went.

The whole evening was awkward. We just ordered a pizza and watched movies, which was what we did in our friend group anyways, but this guy would NOT STOP STARING. I felt like I couldn’t even eat because I was under a microscope. The evening ended uneventfully, but then there was the aftermath.

We kept texting and seeing each other in the friend group, and about a week later he asked when we can have another date. I told him that maybe I had rushed into things too fast and I just wasn’t feeling any connection with him.

“I BROKE UP WITH MY GIRLFRIEND FOR YOU!”

Yup, dude found out I was single, dumped his girlfriend of 8 months just so he could ask me out to an awkward pizza date in his bedroom…

The timely cherry on top is that they got back together, and apparently I’m tearing their marriage apart because she found a bunch of texts from me from six years ago and he admitted that he kept them cause he still likes me. I haven’t seen him in four years.

Edit for timeline: We are friends in highschool (10 years ago) and college (5-6 years ago). While we are in college, he asks me out after dumping his girlfriend. Sometime after that they get back together and are married last year. Last week, a friend informs me that they are on the verge of divorce because she found texts he had saved (screenshots) from our college chats 5 or 6 years ago.

Edit: Several people are commenting that I shouldn’t have gone out with him and just told him I wanted to stay friends… the thread is literally “girls guilted into going out with ‘nice guy'”.

#6

Image source: anon, Matheus Câmara da Silva/unsplash

He was genuinely nice and I thought I was being too picky and maybe I could see this through, if I took the effort of getting to know him. But everytime I offered a contradictory point of view on any generic topic of discussion, he would proceed to casually mock my appearance, attire and my personality, in retaliation to my disagreement. That was the last date, obviously.

Edit: He might not have been “genuinely nice”.

#7

Image source: taikutsuu, engin akyurt/unsplash

All my friends said a guy from our group of friends was very nice, even though I felt like he was creepy. Went out once, thought I’d give it a chance, to be nice. Regretted it immediately.

He asked me what I thought of being in a relationship with him, and when I said no/I didn’t want that (because I wasn’t very interested and we had only been friends before this), he said he was disappointed with my answer and expected something more worthy of him. He said that saying no was disrespectful. Big yikes.

We met once after that because he surprise visited me a few months later. He asked me to ruffle through my hair because he wanted to feel my scalp, treated me like a dog and wanted me to sit next to him so he’d be closer to me. He also thought it was a great idea to mention that he sometimes hears voices in his head and has dreamt of k*****g people.

I rushed him out of my apartment onto the street. I just wanted him to be gone. I checked my keys five times to see whether he took any. I’ve had to see him a couple times since then, and he is the most creepy, socially inept person I’ve ever met. He’s so aggressive and impulsive.. I am truly afraid he will r**e or k**l someone someday, and I’m still afraid that that person could be me.

edit: this blew up. Yes, he still is in my circle of friends. For some reason my guy friends laughed it off and don’t see him as much of a threat to anyone, let alone me. I avoid him as much as I can, and never see him in groups of less than five people.

#8

Image source: dude_areyouserious, Andrej Lišakov/unsplash

I was a college freshman. First week of school, I was in my dorm hangout area going through the calendar on my phone to add exams to my schedule. I didn’t realize that “Nice Guy” was looking over my shoulder as I was doing so.

He goes, “I see you don’t have plans on Saturday, we’re going to breakfast.” – I continually objected and said I just hadn’t gotten around to adding anything to it yet. He wouldn’t leave me alone about it all week, so eventually I agreed to go on Saturday. I was purposely on my worst behavior in an attempt to repulse him because clearly, my opinion didn’t matter otherwise. He ended the date by calling his mom, telling her that he met his future bride, that we were going to give her grandchildren.

He handed the phone to me, so I straight up told his mother that I had no interest and was only there because he wouldn’t leave me be and apparently acting like a barnyard animal wasn’t enough of a turnoff. Mom laughed and said “sounds like my boy!”

He would sit on the couch outside my dorm door to bombard me whenever I tried to go anywhere, followed me to and from classes for two months, and tried to befriend my roommate to get closer to me before moving on to a new target. She ended up with a restraining order against him.

Edit for clarification: This was not my first interaction with this guy. He lived in my (small) dorm building where we did multiple getting to know you exercises that week. He helped a ton of people move in and was a self proclaimed “nice guy” like the title had in quotes. Most people’s first impression of him was that he was nice enough, but a little off. I clearly completely agree that dude was creepy af, I just posted in a hurry and left out some background. Edit edit: since “nice guy” was in quotes in the OP, I thought it was clear that we weren’t dealing wit actual nice guys, hence why I thought my story was relevant. If it were asking a story about going on a date with an actual nice person, I don’t think it would be an interesting AskReddit question?

#9

Image source: dal_segno, Andrej Lišakov/unsplash

I was in highschool and figured I should give the guy a chance, maybe I was just being snobby.

Anyway, we decided to go to the movies.

His older sister came along to chaperone, and spent the movie sitting in my lap* to make sure we didn’t “get up to anything funny”.

After the movie, I said I had to go home…later that night, he calls me crying to confess he’d snapped a picture of me and wh*cked off to it.

There was not a second date.

*Incidentally this was when I began to have an inkling that I maybe liked girls.

#10

Image source: MissFrybread, Yunus Tuğ/unsplash

Went on one date. He just kept talking about how horrible most women are and how gross periods were and v****a in general was also brought up briefly. He was very masochistic and homophobic.

Never talked to him again. A couple years later when I was still in college a friend bumped into him at a party. Found him in a room blowing another dude.

#11

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Moved to another state with my sister and she made a few guy friends. One of them saw her with me and begged her to set up a date with me. I reluctantly agreed because she kept saying how sweet and nice he was. First date he kept gushing about how gorgeous I was and the fact that I was smart made it 100x better. He was going to make me his queen and take me around the world but I have to pay for my own meal and his since he paid this time. I told him I was only interested in being friends and he begged my sister to get me to go out on another date. I declined and we moved back home and he came to visit my sister. While he was here he kept looking at me and telling my sister to just hook him up with me. It was my birthday and I kind of just rolled my eyes and was like come on I’ll take you out too with my group of friends. At the bar, he was really into me and I was getting annoyed because he wouldn’t let me relax and have fun. I told him I really only saw him as a friend and in front of everyone he yelled at me saying what a horrible person I am for leading him on, nothing but a w***e etc. I ended up crying because it was so embarrassing. My guy friends wanted to go “talk” to him after they heard what happened. My sister ran up to me and told me to go make him happy again he came down to see me and this is how I was treating him. I just went home and the next morning my sister told me how sorry that guy was and he wanted me to come say bye to him at the airport. Needless to say I didn’t.

#12

Image source: TVsFrankismyDad, Sed “Creatives” Sardar/unsplash

Badly. Seriously, it was the worst relationship of my life. He was the nice guy who was always there for me, etc, etc. Until we started dating. Then I saw his mother more than I saw him, when I did see him he pressured me constantly for s*x, and he cheated on me.

I think he just built me up in his mind so much, that it became more about “winning me” than actually liking me, so once he got me he had no reason to be so “nice” any more.

#13

Image source: yeahokaymaybe, Faruk Tokluoğlu/unsplash

After a few years of tepid friendship (something was always a bit ‘off’ about him, but I thought he was such a nice guy and I was just being a judgy b***h, plus he always claimed to be so in love with me), I agreed to a few dates with my friend. On one date, we went out with a whole group of couples to this state park a few hours away, and during the ride home, I dozed off. I woke up to him groping me under my clothes, and when I told him off, he twisted it around like I was being ridiculous and imagined his hand under my bra. Like, we’re on a date, why was I being so weird, etc etc etc.

When I told him I had to cancel out 4th date because I’d gotten grounded after accidentally setting the kitchen on fire, he punched me. Mostly in the face. *Punched me*.

He spent the rest of high school periodically stalking me/my sisters, ranting and raving to literally everyone about how I just didn’t understand and he loooooooves me, he’s just so emotional with his true love for me that sometimes he acts without thinking, he’s not like those other guys that would make sexual comments about my appearance, why did I have to be such a Stacey, he’s the best friend I ever had until I ruined it all by willfully “misunderstanding” and refusing to hear him out or give him closure, on and on.

What a nice guy. Guess he tried to break into my bedroom window out of love and concern, huh?

#14

Image source: anirezz, Getty Images/unsplash

He was the nicest guy I’ve met. Super sweet and charming and all that good s**t. Good at ACTING nice, sweet, and charming, that is.
I’ve always noticed how self-centered, guilt-tripping, and manipulative he was but hoped he’d grow out of it.
He did not.
Then after so much psychological abuse from him, I finally just snapped. Then, from his perspective, I somehow ended up being the person who guilt-tripped him and abused him and I had soo many red flags.

Go figure.

#15

Image source: lamethrowaway18, Blake Cheek/unsplash

As it turned out, he lied about just about everything, from his favorite movie to his moral opinion on bathing suits.

He would not take no for an answer. If I persisted, it meant I didn’t love him. He often threatened not to kiss me ever again if I didn’t do xyz (like send nudes, do certain sexual things, etc).

He taught me that my opinion and my feelings meant nothing. Even on a basic “how was your day” level. At first he would ask and acknowledge my answer. Then he would ask and then immediately change subjects, as if he hadn’t heard me. And then finally he stopped asking.

But he was a catch. Girls never gave him the chance he deserved. They were all missing out. /s.

#16

I married him! Literally the best, most reliable, dependable and sweet guy who supports me in absolutely everything. Gives me everything I never knew I needed. He is my absolutely hero and I couldn’t be happier!

Image source: nuitnoir23

#17

Image source: SleepySlowpoke, Kate Miheyeva/unsplash

Wasn’t really a date. I was at a hiking trip with my sister and other people from our village when we met a group of guys, drinking and having fun. Was on (german) fathers day, so it wasn’t an unusual sight. For some reason my sister got into a talk with the guys and somehow got me and her invited for the party at one of the guys house later. No big deal, we brought her boyfriend with us and were expecting some good time. My boyfriend was on a biking trip with his dad, so he couldn’t come.

We arrive and nobody else is there, guy says they will all arrive later and we are early (30 minutes after the time he told us to be there) and we start drinking, having fun and everything. He clearly has a thing for me, invites me to go on festivals with him, sisters boyfriend tells me I would be stupid if I say no and he would totally be going. The others arrive and at some point the homeowner asks me to go out for a walk, he needs some air.

We walk a bit and suddenly he turns around, telling me I am the love of his life, the girl meant for him, most beautiful, smart etc. he has ever seen. I was shocked and didn’t know what to say except “I have a boyfriend, you know..”, he said he doesn’t care, we’re clearly soulmates and then just kisses me out of nowhere. Tells me he would break up with his girlfriend for me (he never mentioned her before) and I should do the same.

Luckily, my sister blacked out on the toilet and someone shouted at him for help unlocking the door, so we went back up. I took care of my sister, his girlfriend arrived, he pulled me aside and told me he would do it now, right here. I said “no” and he told me to take my sister and leave, what I did then. He messaged me on facebook the next day that I was a w***e and I lead him on and he almost broke up with his future wife for a b*tch like me.

Tl;dr: Met a guy, got invited to his house, he wanted me to break up with my boyfriend, he wanted to break up with his girlfriend, kissed me, called me soulmate and then a w***e when I said no. All within 24 hours.

Edit:
Since a lot of you asked “why would you let a stranger kiss you” or if I told my then-boyfriend about it… we did not make out and did not kiss him back. He smooched my lips after he approached me in the middle of a sentence at high-speed and let go of me seconds later before I could even process what had happened.

I CAN take care of myself and would have given him a good kicking, but I honestly was worried about my sister, even though I used the word “luckily”. At least I could make you laugh about that.

#18

Image source: Andromeda321, Getty Images/unsplash

Most were just awkward, but I do remember one that got horrifying. I don’t remember quite how we got on the topic of conversation, but in an attempt to get me to see that feminism was bunk, he asked me “would you rather be r***d, or sent to jail for 20 years?”

Night ended pretty quick after that. I’m still not quite sure what he was going for there except proving the opposite of his argument.

#19

Image source: RtrdedN00B, Allef Vinicius/unsplash

Well I might not be a girl I was the nice guy in my first “relationship”. I was meeting a girl which I knew from a friends girlfriend. Well at first everything was nice and we weren’t having anything serious just meeting like friends playing paintball and billard and so on… however I really liked her and she did recently break up and I tried to cheer her always up … so then I asked her politely if she would consider trying a relationship and to my surprise she said yes. I was the happiest guy on earth this day.

So we started dating seriously going to cinema and doing stuff alone. But I don’t know why however I really got clingy. Like I wanted to see her all the time I wanted her to come over to me and it ended up creeping her…which in hindsight I really understand and she got continually creeped out until she broke up and I was devastated. I didn’t force her to anything but I was as I said clingy. After that I was depressed for over a year and than got my s**t together however I am sorry that she had to experience me like that and I also apologized for that and now we are just normal friends. Not as good as before but well.

But all in all it ended up good for me since cause of that I ended up with my current girlfriend and without seeing my failures from past I wouldn’t be able to hold this relationship.

#20

Image source: inked-ocb, Michael Tucker/unsplash

I was that girl who loved the bad boys.

My nice guy had been my best friend for a number of years and I always knew he liked me but I was busy chasing a******s.

9 years we were best friends and grew up together and he watched me pick all the wrong people and get hurt. Other friends kept telling me to give it a chance etc. Two years ago he asked me to come over for dinner – it seemed fairly casual until I realised he’d asked me for Valentine’s Day. I can’t say I was guilted a-such but it still felt a little awkward. I was mega nervous thinking it was gonna be so awkward but when I turned up it was fine he’d cooked me a meal, bought flowers, a bottle of wine and chocolates and lit candles on the table. I don’t drink much so he ended up getting through the whole bottle of wine because he was so nervous but it was a lovely evening and things felt very natural so I decided to give it a go.

We’re now headed towards our 2nd anniversary, have a lovely home together, a beautiful (but evil) Egyptian mau cat and couldn’t be happier. Because we were friends first we know we get on, we finish each other’s sentences and never run out of conversation. Yet to have one argument that goes beyond whose turn it is to wash up lol. He is genuinely the best thing to happen to me ever. Sometimes the nice guy does win!