Online dating is a lot like gambling: sometimes you win, and sometimes you lose. These men share how they tried their best to find love, but instead, they just found straight up crazy.
(Content has been edited for clarity)
She Brought Along An Unexpected Plus One To Their Date
“We meet at a local pub for a few drinks, and we get chicken fingers. The conversation is terrible, but I notice she’s taking the chicken fingers and ripping them up in her hands and putting the breading in her purse. So naturally, I call her out on it. She smiles and says, ‘Oh, I’m just feeding Sammy’ as she pulls out a fat chinchilla from her purse. She plops the thing in the middle of the table, and it just chills out.
I play with the chinchilla a bit, and she gets mad at me for playing with it and back in the purse it goes. I am ready to call it and leave, but she mentions she could go for some ice cream, and I am cool with it. So we go to Ben & Jerry’s. We get to talking about tattoos and piercing, and she tells me she has chest piercings, and I’m like ‘Oh?’ and then she pulls down her shirt, in the middle of Ben and Jerrys at 8 p.m., and shows me her chest. I just kind of poker-face.
So then I decide to walk her to her car. She kiss attacks me, and well, she is cute, so I make out with her, sort of, her lips are tense the whole time, and she licks my teeth. I friend her on Facebook for some reason after that; she has a Facebook page for her chinchilla that had more Facebook friends then I do. A few months later the chinchilla dies, and its Facebook was a memorial page where a bunch of people (like, 35) comment how much they miss it. I ‘like’ one of her statuses and she calls me crying. I unfriend her but not the chinchilla. RIP Sammy.”
She Just Loved Playing The Victim
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“I met up with a girl for the first time after talking for a few weeks. She is attractive and fun. We have lots of things in common. During the date, she keeps checking her phone and acts annoyed by someone. Finally, she apologizes for it and tells me about some creepo stalker dude that won’t leave her alone. And I guess to prove it she calls him and kinda loudly says ‘Stop contacting me or I will call the police!’ Fast forward to the end of the date; she says she had a good time and wants to do it again sometime, kind of flirty. Then outside before she gets in her car, she goes in for a long passionate kiss. Then says ‘Call me’ and winks!
So I call a couple of days later. No answer. I text the next day, still no answer. I call in two days and finally, she answers the phone and says loudly ‘Stop contacting me or I am calling the police!’ I could just see her on a date playing the stalker victim again! Crazy!”
She Was Just Too Messy For Him
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“We meet up, and she’s immediately asking me about my job and salary. We have a similar job, with it being a new role and she’s been there for a while, so she’s making more than I am. Good for her.
We get some drinks. I hit the bathroom, and when I come back, there are three drinks on the table. One for me and two for her. Interesting. Maybe this means I’m getting lucky.
She downs her drinks and orders another two. I’m still working on my first drink. She starts talking about how her friend is getting married, and she’s single, and her life isn’t going anywhere. Then she starts crying. THEN she calls her friend and invites her out on our date.
Next thing you know, she’s in the bathroom, barfing. She comes back covered. She’s crying, she pooped herself, she doesn’t have any money on her, so she hopes I don’t mind being stuck with the $100 tab.
She messages me the next day telling me I’m a jerk for not calling her, and maybe we should try getting together again that night. Nope!”
She Just Couldn’t Take A Hint
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“The girl lied about her weight in her photo. When we met, she said she would hug me, but all four cargo pockets on the front of her jacket were filled with broken glass. There was some broken glass at her workplace, and she was tasked with cleaning it up. Guess she decided that was the best place for it. I was then regaled with a two-hour tale about her Harry Potter fan-fiction, and all my attempts to politely change the conversation were brushed aside. It got to the point where I dropped all pretenses and started chain smoking and texting other people. She didn’t seem to mind and kept talking.
I didn’t respond when she asked me for a second date.”
He Should’ve Realized This Woman Had Class And Standards
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“I started meeting slightly older than myself women online for ‘no string attached’ fooling around time. I was 30 at the time, and most of the women were over 40. It was basically, chat for a day online (or not), meet up in a pub, half a drink later and then go back to their place or a hotel to mess around. I’d probably done this five or six times when I met a 45-year-old ‘posh’ lady online; we agree to meet up in a pub. I get there, and she’s already there, looking quite a bit older than 45, more like 55 and matronly for want of a better word. She’s worse than the usual older women, but I’m now aroused and decide to go along with it anyway.
We chat, have half a drink and, then she suggests we get another drink. I finish the second drink and then ask if we’re going to get a hotel or go back to her place. She gets upset, asking if I think she’s some easy woman, and she doesn’t do that sort of thing. I get embarrassed, go bright red, say ‘Oh I must have got the wrong idea.’ We awkwardly chat for another five minutes and then I excuse myself to go to the toilet. I skulked out the back door of the pub and to my car, as I drive round to the front of the pub, she comes out and throws the content of her drink at me, calls me a pervert wanker and I drive off spluttering.”
Sometimes Distance Doesn’t Make The Heart Grow Fonder
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“I was in middle school when AOL first came out. In one of the first few days in which my family had it, I met a girl in a chat room. She was a few years older than me, and we happened to live in the same state. We had a pretty solid connection and talked a lot for about year or two; online, over the phone, through letters, all the goofy stuff teenagers do, and we even sent each other pictures once. I guess you would call it a relationship. Anyways eventually we got rid of AOL and we sort of lost touch for a year or two, but once AIM came out we found each other again. By that time we were both in high school, I was like a freshman, and she was a senior, and we were both dating people, so we became more like pen pals. We always talked about meeting in person but we lived about 10 hours apart, so I never really thought it would happen, and once she graduated HS I believe she joined the military if I remember correctly and we lost touch again.
Skip ahead another two years or so, and I’m a senior in high school. One day during spring break after one of our high school baseball games some teammates and friends of mine come back to my house to hang out. We get there, and my youngest brother is home and says some girl came to the house looking for me and asked to use our computer. I have no clue who it is, so I asked my friends to hang around. About 30 minutes later she shows up, totally catching me off guard. Apparently, she was visiting some friends two hours away and wanted to make a surprise visit.
The next 4 hours are some of the most awkward moments of my life, and not only that but I morphed into a total pinhead. I didn’t want to be alone with her because I had a girlfriend (whom I’m now married to), and I wasn’t attracted to her. I had no idea what she wanted to do, and I wasn’t entirely sure what she was expecting. So sensing how uncomfortable I was with the situation my friends and even my brothers start to leave, and all I have left is one friend and my mom. So for the next 4 hours, my friend and I sit in my living room playing PlayStation while she watches and makes awkward conversation with my mom. I think at one point she did order us a pizza which was cool and she may have even fallen asleep on our couch for some portion. When she got up to leave, I walked to her to her car and said goodbye and never saw or heard from her again. I tried finding her on Facebook, but she’s either not on it, or got married and changed her name. So if you’re reading this J, I just want to apologize for how I acted, it was out of character. You just caught me way off guard and being 18 I didn’t know how to react, I’m sorry.”
“When You Find Meaning In Your Life In God, Call Me”
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“I met with a woman who started a conversation with me on an online dating site. I wasn’t there so much to get to date, but I just graduated college, my friends were mostly gone, and I wanted to make some friends.
So, I meet with her (it was understood that this meet up was indeed a date, not a ‘friend-finding’ thing). She is older than me, something she kept pointing out. In general, she’s nice, has a good job as a speech therapist, thinks what I do is interesting (advertising), and it’s going pretty well.
Near the end, she gets a serious look on her face. She says that she wants to get married, and have kids. I say I don’t really like kids, and I’m not a fan of marriage as a whole, but I am not opposed to it if the right person comes along. Well, I guess she glazed over those answers in her mind, because then she says, ‘I am very religious, so it means a lot to me that you are.’ I said, ‘Actually, I have no religious affiliation at all, it’s not important to me.’ Well, she gets up, puts on her coat and says ‘Well it’s important to me that you are. When you find meaning in your life in God, call me.’
I have not called her.”
He’s Still Waiting On This Special Package
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“I met a girl on Match.com that wasn’t truthful about the fact that she had a kid in her profile. After we met, she told me she had a daughter, but I let it slide because I was attracted to her and she was an aroused girl. I ended up sleeping with her on the second date and we hooked up a handful of times over the course of a month. But she ended up being quite the drinker, every time we would hang out she would pound a bottle, sometimes more. Having dated a big drinker in the past, I didn’t want to go down that road again, so I ended it. That’s when she decided it was time to be conveniently pregnant.
Even after I called bull, she kept insisting that it was true. I asked if she would let me go to a doctor with her, but she wouldn’t let me. She texted a picture of an ultrasound with her name on it, but the date blacked out. (It was the ultrasound when she was pregnant with her daughter). She kept sending me messages telling me it was true but refused to give me any proof. I never believed her for a second and told her that. She eventually caved and told me she was lying. Fast forward a few days, she was miraculously pregnant again. She told me she was going to send me a packet with the proof I needed…she never did. One year later, I’m still waiting for that packet.”
The Legend Of The Bog Witch
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“A girl messaged me one night on OkCupid. The message was short and went something like, ‘Hey, you’re cute. I love zombies too (I mentioned in my profile I’m a professional zombie actor) text me xxx-xxxx.’ She looked decent in the one picture she had up, which really should have been a red flag. I texted her, and she wanted to set up a date for the following Monday, January 3rd (2011).
Fast forward to that night, and I’m driving to pick her up because she said she didn’t have a car or a job. Red flag two. When my GPS led me to an empty grassy field, I called her, and she told me to wait in the parking lot of the nearby Panera Bread. I waited a few minutes, and after a bit, I saw a figure emerge from the treeline at the back of the field. I could see it was my date. Her hair was black and greasy in front of her face, she wore this billowy fishnet thing that kind of hid her figure, but the worst part was her lazy eye that just…rolled and rolled about in her socket and would settle and stare just several inches away from my face, so it seemed like she was staring at an invisible horn growing out the side of my head. I should’ve fled, but I was too much of a nice person and if this bog witch wanted to go on a date, then by golly I’ll do it.
We went inside, and I immediately discovered I had a pet peeve for people who talk several decibels higher than everyone else. I grabbed us a booth in the far corner, so she didn’t end up shouting our entire conversation. I said to her, ‘So, tell me about yourself,’ which was probably the worst possible question for me to ask. She began with talking about how she’s not like other girls; she could pull off the goth/emo/punk look all at once, that most of her friends were furries and they’d love to meet me. She was also looking for an obedient sub, she enjoyed watching tranny threesomes, and she loved foot torture. Now, this was the third red flag, but, at this point, I made my bed, and I was sleeping in it. She asked me about myself, and I went on about my normal hobbies and interests, and she was fighting me all along the way, telling me that airsoft promotes weapon violence and that I’d never go anywhere with a degree in graphic design (I did, thanks). She cut me off and asked me to talk about any female friends I had. I began to describe a few when she kept jutting in with ‘Well she sounds like a witch!’ and ‘I don’t think she likes you!’ I stopped and asked her if she had a problem, and she dropped this line: ‘I need to eliminate all competition if I’m going to have a chance with you.’ Uh, no.
There was a long pause as I ate my food, but she eventually broke the silence with asking me, ‘Do you know what breaks the ice? Getting intimate. Want to hear a personal story?’ What wasn’t personal already? She went on about some past relationship and how good it was and everything seemed fine until it ended with: ‘…and then he gave me herpes.’ Now that was all the freaking red flags. I stood up, told her it was nice meeting her, but I had to leave. She followed me out and got in my car with me (of all the times I left the doors unlocked). She demanded I drive her home. She told me to pull up into the grassy field, which had a dirt road I couldn’t see earlier. The dirt road went into the woods, and I expected it to come out upon a clearing with a dilapidated shack and a firepit with animal bones and a bog which she’ll walk into and sink back to the depths from where she came. But no, it came out to a rather nice looking house. But then she dropped the line, ‘Yeah, I’ve been living here for the past two weeks with a guy I found on Craig’s List.’ I pulled up, she tried to kiss me, I pushed her back, told her to get out of my car, and I drove away. I still remember her silhouette waving to me in my rearview mirror. I sped home, took a shower, acid-washed my face, burned my clothes, and cried myself to sleep until Sunday morning (remember, it was a Monday). A lot more has happened since that day, but this was the initial date. I ran into her twice more in public since that day, but thankfully she never recognized me because I was in costume.
The first time I saw her, she was holding hands with some gangly looking dude and the second time I saw her she was pushing a carriage. A friend of mine who I told this story to met her at a Halloween party and became friends with her. When I saw the photos of them arm in arm with each other on Facebook, I flipped my lid, told my friend she had become friends with Bog Witch, who then promptly dropped contact with her. Sometime later I had a falling out with this friend, and I guess in her version of a sick joke texted me a pic of pregnant Bog Witch she found online. She looks like a fat gimpy hobbit. I show people the pic who don’t believe me. This date-gone-wrong had become a bit of a legend amongst my friends, and I usually end up telling it at every party.”
He Learned Never To Be X’s or O’s In Future Messages
“We met on PlentyOfFish. I sent her a message, and she responded saying something like ‘Hi! You seem nice; I’d rather text than chat here. Here’s my number.’ I thought OK, that’s a little unusual, but I’ll roll with it. So the next day we texted for the whole day, getting on quite well. In the evening she asked if I’d like to chat on the phone. Now I wasn’t expecting this, and it made me nervous, but I agreed. So again we got on well, we chatted for a couple of hours and arranged to meet that weekend.
In our conversation, I picked up that her self-esteem maybe wasn’t high, but hey that’s no real problem. Immediately afterward she texts saying ‘I like your voice,’ I couldn’t decide whether this was creepy or cute, so I shrugged it off.
The next day I was busy at work, around midday she texts me with ‘Hey :).’ I immediately thought ‘Oh no, not one of those.’ I replied briefly, she replied, I replied, etc., but basically, I wasn’t very responsive as I was busy at work. Over the afternoon she texts more and more becoming incredibly needy.
Around the time I got home from work, I got a question ‘Why fewer kisses? 🙁 xxx.’ This confused me, so I asked, and apparently, I’d put a couple of kisses after the texts the day before and only one that day. I laughed it off, said it wasn’t a big deal. She responded saying it isn’t a big deal, but she would like to know why. This escalated throughout the evening, me feeling incredibly trapped as I’d arranged to meet her for a date and she already seemed to think I was her boyfriend, and we had our first argument.
In the end, I diplomatically told her I think she needed someone a little more attentive than me and left it at that. I got a barrage of texts moaning at me then it died off. So much trouble for a girl that I didn’t even fancy that much, but just seemed quite cool.
As I write this, I remember that as I understand all you Americans out there don’t go for the whole kisses on texts thing. You’re right to do so! I no longer add any, it’s a ridiculous convention.”
He Could Write A Novel About Horrible Online Dating Experiences
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“I used OkCupid and other sites, for a bit. I met some winners. Above and beyond the weirdest encounter was a girl that messaged me.
A little backstory: I was near 300 pounds at the time my profile picture was taken. I didn’t feel the need to change it, as I hate pictures. I lost 100 pounds at the time. I was lean and in shape, figuring this was ok… as most the time it’s the opposite problem of gaining.
We start chatting; this girl is a 9, almost a 10 for me. Dark hair, thin and has her own place. In internet dating, this is a gold mine. So we set up a time to meet in a local town where she goes to college. After work, I make my way over to said town to the Denny’s. She tells me that she is there and sitting at a table by the window.
I walk in and tell the waitress that I am looking for someone I am meeting. It’s not busy, but there are several people. Suddenly I get a text. It’s her. She says, ‘No thanks, I thought you were bigger.’ It turns out she was scoping me from the parking lot, and bigger guys were her thing.
Other oddities in dating were from PlentyOfFish: She was into roleplay and loved the Bonnie and Clyde/Harlequin and Joker idea. Trying to expand my boundaries (and she was friggin hot) I say ok (I’m still about 250 at this time). She knows how big I am and it’s fine. We talk on the phone, and then we hang out at her place. Her friends are there, and we are getting along great. They leave, and we are alone. She comes back with costumes of Joker and a skin-tight Harlequin custom. Swwwwweeet. We do the deed, and it was fun. The deal breaker came in the middle of the night. She declined to mention she believed in certain things. I wake up to candlelight and her at the end of the bed in a black gown with tarot cards just murder staring at me. She screams ‘YOU ARE GOING TO BREAK MY HEART’… I’m out.
Another winner was an addict that told me she wouldn’t put out except if she were married. That night she stupidly texts me to come over and bend her over a picnic table.
Another one for PlentyOfFish. This girl messaged me and said she liked my profile and I didn’t seem like other guys. I was shy still and socially awkward. However, I was beginning to get my life together. My weight was about normal again, and I had a good steady job. None of that matters as we never went on a date.
She gives me her Facebook, and we are just having a great time messaging. This chick is a blast, and she’s all over the place. Something I find endearing. The conversation just moves right along. And I guess I upset her when she just errantly says, I want some gobstoppers” just after talking about her cat. I said, ‘that’s weird.’ Everything goes dark. Facebook removal and PlentyOfFish blocked to her profile. Just gone. Meh.
I started talking to a girl, and she was really in the throes of depression. Life had beat her into submission. Which was fine by me. I was indeed in a bad phase as well. I was just trying not to be lonely. This girl and I talk for about a week. I find out that I am working near her house, so she invites me over. It all seems great. We are hanging out watching tv, and it’s about to winter storm. So I mention that I need to get going and she asks me to stay (shawing).
We are both large (this is the defining moment I went weight loss centric) and things are easy for us to do but we get it done. We enjoy each other. So for the next week, it’s just us having fun, but she lives with her mom and stepbrothers (everything about the stepdad was absent).
Well, I had a pretty bad childhood. Some people took advantage of my always out-of-it mom and I ‘stayed over’ at someone’s house a lot. Barring going into it, I’ll just say I was a victim of some child assaulters. Well, I hold this secret pretty close to certain situations, involving real life. People like the following actually exist.
I told her about my childhood, and apparently, she told her mom. I got to her house one night about week three, and her mom had a bat and was standing at the door telling me to ‘Go away.’ She didn’t want me around her boys because I may have urges to do to them like what was done to me. She claimed she talked to the police and if I went inside, they would arrest me for trying to fool around with her boys. Her boys were standing there with the ‘what the heck?’ face. The girl I WAS dating was crying.
I still am not mad at her or her mom. I’m shocked. It was the first time something done to me has been held against me as an adult. Attributing it to ignorance is the only thing I could do. But I never spoke to that outfit again.”