Horrible Online Dating Stories To Keep You Single


Holy shit: the internet is teeming with awesomely horrible people for you to date. We asked for your stories, and you good god, you delivered. Let’s skip the foreplay and get right to the dirtiest half-dozen.

1. Say Uncle

I have known a girl — who we will call Molly — since we were young. I know her immediate family very well. We grew up and drifted apart, but stayed friends on Facebook.
Flash forward to last year, when I was a college student. I received several messages from a cute lady on OkCupid, and I was psyched until I saw that there was a steep language barrier and she was looking for women to have sex with her while her husband watched, which is not my bag. They were all about a subservient master/slaves relationship, with the big strong man dominating the little women. Her entire profile was “my master” this and “my master” that; he was this remarkably jacked bald white 40-something, and she was a slender, pretty Asian 20-something who had met him while he was stationed overseas. Her pictures didn’t show full frontal, but she basically came as close to all-out porn as she could without breaking the rules; mostly in costumes obviously meant to play on her heritage, and all of it with coy sexual captions about how her master likes her holes.
I glanced at the master’s profile, saw his thoughts on feminism (the only time he gets in touch with his feminine side is to give it a firm spanking like the dirty little slut that it is), snorted, and moved on.
Or so I thought.
This summer, I started flipping through photos of my old friend Molly that had been tagged on Facebook. I came across one in particular, and I stared at it for a while, because I couldn’t figure out why the man with his arm around her looked so familiar. The caption said that Molly was his niece, and I eventually decided that it was pinging me strangely just because he looked like his brother, Molly’s father, who was almost like a second dad to me when we were kids.
Then I clicked “next” in the album. It was a picture of the woman from the OkCupid sexytimes pictures. I realized why Molly’s uncle had looked so familiar: he was the proud anti-feminist who had wanted to get off on me having sex with his wife.
So now I’m in this weird place where I’ve seen mostly-naked very sexual pictures of my childhood friend’s aunt dressed up like a Vietnamese prostitute

2. Spooj On The Beach

I met him on Match, which I’d joined as an attempt to tiptoe back into dating after a very painful divorce. He sent me a message saying my profile was intriguing and he would love a shot at meeting me.
I looked over his profile and quickly deduced that we weren’t a match. He had written a long missive about his passion for football and annoyance with women who didn’t understand (at the time, I hated football), and he claimed to be a devoted Christian and a staunch Conservative (I am neither of these and don’t much enjoy hearing about either). I politely declined his request for a meeting, and this seemed to only egg him on. I’d say, “I don’t meet any of your clearly articulated criteria,” to which he’d reply, “Maybe you’re worth opening my mind a bit.”
We went back and forth for a week or two with me insisting we weren’t right for each other and him playfully arguing that I was too interesting for him to let me get away. He said he’d become accustomed to women throwing themselves at him (apparently he’s some sort of successful business owner and semi-pro ball player, yay!), and he found my reluctance “sexy and endearing.”
I’ll admit, I was flattered by his persistence and impressed by his confidence, so I finally agreed to meet at a restaurant for dinner. He was decent looking, although a big hoss of a fellow, and he came across as intelligent, witty, and confident in person. He said he was recently divorced and had a 3 year old daughter. He seemed nice enough, but I really wasn’t feeling a spark, and after a couple hours, began to find his self-assurance somewhat obnoxious. For reasons I still don’t quite understand, I nevertheless agreed to join him for ice cream after our meal, and accepted his offer to drive.
We live near the coast and somehow he talked me into pulling into a parking lot near a public beach to chat and finish our ice cream. Although I didn’t really think it would work out, I let him kiss me (What can I say? It had been a while) and when it got a little too hot and heavy, I stopped it and said I was ready to head back to my car. He started whining and begging me for sex, saying that I couldn’t just leave him in turned on like that. At first I laughed it off, but he grew increasingly desperate, telling me he was “about to explode.”
“Can’t you just suck it or at least give me a handjob?” “Umm, no,” I said. “I think it’s time to go- NOW.” He got all frustrated and annoyed, like he was offended that I’d been willing to kiss but unwilling to fuck, and I started to get pretty nervous. That’s when he whipped it out of his pants and proceeded to masturbate, right there in the driver’s seat. I was too relieved that this massive dude hadn’t tried to rape me to feel scared, and I had to force myself to look away, trapped in a combination of absolute horror and fascination.
He sat there stroking away enthusiastically, moaning about how good it felt, while I pressed myself against the passenger door, trying to stay as far away as possible and looking around for potential help in case things got any worse. When he was almost finished, he said in a breathless voice, “Where do you want me to put it?”
When I didn’t respond, he continued, “Where should I cum? Can I put it on your tits or can you at least give me your hand?” I ignored him, so he let it loose all over the steering wheel of his truck. “Oh my god, I am so embarrassed,” he said. “I can’t believe I just did that, but you are so sexy I couldn’t help it.” Then he casually asked me to pass him a napkin from the glove box so he could clean up his mess.
I probably should have just run away, but the empty beach at night seemed more dangerous than this now-spent perv, so I let him take me back to my car. He acted like nothing strange had happened and told me he’d had a great time. As soon as I saw my car, I ran without even looking back and went home and showered.
He actually sent me another message asking for another shot. I disable my Match account and basically disappeared from the cyber universe for months. Technically, I think it probably qualified as some sort of sexual assault, but after telling the story of the “Masterdater” to my friends over and over, I had laughed too much to feel traumatized.
A few months later, I was eating pancakes at IHOP with my new boyfriend (now husband), and I spotted the Masterdater eating with a woman and a 3 year old little girl. Both of them were wearing wedding rings, and from the look of panic on his face when we briefly made eye contact, I feel pretty sure he was married the entire time we corresponded. After what I’d let him get away with, I was very tempted to go over and ask him if he’s whacked off on any first dates lately. If only the kid hadn’t been there…

3. Crash Into Me

After we ordered a pizza and settled in to watch the first movie, he paused it, turned to me, and started ranting about how women are whores and how hard it is to be a rich guy. I was really uncomfortable and told him so, and he apologized and resumed the movie. Five minutes later, same thing happened again. I firmly told him that I’d like to go home, so he said he’d drive me. When I get into the car, he peels away so fast that I can’t get my seatbelt on. He hits a cement pillar on his way out and the hood of his car starts to smoke, but he doesn’t stop, and he’s going so fast that I am slammed into the door, him, the windshield, etc. like a bean in a tin can. He starts saying crazy stuff like, “Oh, I’ll get you home, but I don’t know what condition you’ll be in when you get there,” and “Oh, I’ll get you home, I don’t know when, but you’ll be home sometime!” I was so scared. Still couldn’t get my seatbelt on. Someone suddenly pulls out in front of him and he slams the car to a stop; I hit the windshield, and in an incredible feat of awesomeness, grab the handle of the car and open it, propelling myself out of the car as he hits the gas pedal. I hit the ground and started running as fast as I could… I ducked behind cars in a parking lot and crouched behind them until he drove away.
I called my roommate and she wouldn’t answer her phone, and I didn’t have anybody around, and my purse was in that loser’s car, so I ended up walking a few miles until a cab went by; I convinced him to drive me to my mom’s (far away) and that she’d pay him when I got there.

4. Muppet Pleasure Island

A couple of years ago, I joined jdate; set up a profile, added a couple of pictures, noted a couple of my interests – as you’re meant to do. I started chatting to a couple of guys on there who seemed interesting and then I was messaged by ‘David’.
David seemed sweet – reasonably witty, decent banter, liked the West Wing – what wasn’t to like?! We exchanged numbers and agreed to meet the following week at a pub down the road. Success! My first Jdate!
I should at this point mention that, although I don’t really remember exactly how the conversation turned to this, I must have mentioned that I like the Muppets. And I do like the Muppets – again, what’s not to like?! But it was a throwaway comment and I obviously did not think much of it at the time. How wrong I was.
We met the following week; I was full of excitement, he brought along a duffel bag…… and there was no spark at all. The witty banter I had come to expect from him was just not there – he was nervous, fidgety, and told me, once I’d ordered a glass of wine, that if I died on the road that night because of my drinking that he would not feel guilty.
Stuck for something non awkward to say, I asked him why he’d brought along a giant duffel bag. His eyes lit up and mumbled something about how he’d hoped to save them for later in the evening to ‘spice it up’ but since I’d asked……he unzipped the bag and from within, pulled out – Kermit. A full sized, proper, hardcore Kermit the muppet. He put Kermit on his knee and started to do what I believe was his Kermit impression. Believe me, it was not Kermit, but someone sounding exceptionally constipated.
I like to think of myself as a reasonably nice, polite, North West London Jewish Girl, but even I couldn’t see a way out of this. He told me he had 40 other muppets at home and that since I’d told him that I also loved the Muppets (?!) we were obviously meant to be. Obviously….we were not. I made my excuses, downed my glass, and headed for the door.
He still messages me to this day and if I ever see him around (unfortunately, the Jewish social scene in London is smaller than I would like), I tell him I have a boyfriend.

5. Pussy Control

Let me start by saying that I was really only looking to hook up. I had just been dumped by my boyfriend and am not the bar type and so I figured that online dating would be a reasonable option. I used a local personals service (“_city_dating.com”) and had been talking to a guy for about two days before agreeing to meet him. “
Mike” had told me that he used online dating because he was suffering from depression and was on medication that made it hard for him to perform. He decided that it was easier to meet girls this way than to meet up in person and then have to explain when they started getting physical. He went on to tell me though that he “had a good feeling” about me and that I was “exciting” to him despite his medication. Okay. I was cool with this and decided to go over to his place to see if we really did have chemistry since we both seemed to be looking for the same thing (a hook-up).
When I got there, he was waiting for me in the living room and we started making out. I could tell that he was getting a little aroused but was having some issues and so when he said that he knew what would “help” and that it was in his bedroom…I willingly followed. Walking in I couldn’t help but notice his bed…surrounded by cat condos. Lots of cat condos. (Some structured to be as tall as I was). I knew he had cats but I assumed he meant one or two and that they were just hiding when I came over. Nope. He had nine (or ten?). Which all came out from under the bed when we sat on it. And all went to their perches on the cat condos to watch us (after rubbing against him and being petted quickly). He then proceeded to start making out with me again and was…well…massively aroused at this point. I was massively creeped out. I like cats (I have two myself)…but having them watch me pee freaks me out much less watching me have sex.
I excused myself openly admitting that this was too weird for me and left. He followed me and begged me to give him another chance and “help” him. I left. For the next few days he messaged me asking me to come over and saying that he had “made progress” with me. I blocked him after receiving a photo of him nude, on the bed, surrounded by the cats.

6. The Rerun

When I first moved to my present city, I had time to kill before a vacation. Lots of time. So I went out on a date with a guy from Nerve. He spent most of the date staring at me with a disappointed look on his face. The conversation was stilted – to the point where we started talking to the table next to us because we had nothing to talk about. While there clearly wouldn’t be another first date, I was totally fine with the idea of sleeping with him and never speaking again (I was in the midst of a dry spell and also fuck you I make no apologies). After the date, he said something along the lines of, “well, I don’t really think there’s any reason to go out again. There was no chemistry and the conversation was pretty bad.” I was taken aback. I mean, completely right, but damn, it’s not 100% my fault and who the fuck says that anyway?
Anyway, he defriended me on facebook, I deleted his number and went on with my life.
So fast forward to May of this year. I’m on OKCupid now, and while browsing, see that he is too. Same username, same pictures. I immediately “hide” his profile and forget about him until July, when I “viewed” his profile to see what would happen.
What happened is that he messaged me and asked me out. And not to give me another chance. HE DIDN’T REMEMBER ME AT ALL. Really. Not even a little bit.
What else could I do but say yes? A social experiment, right? I figured it would give me a) validation, b) a chance to see if I’d changed in a year, and c) a fun story.
Due to various scheduling conflicts, we didn’t go out until last week. You could probably guess the results: he likes me and wants to take me out again.

Yeowch. All of these fucking suck, but which is the worst? Let the people decide!

Vote early, and vote often!

Image via Khomulo Anna/Shutterstock.

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