10 F*cked Up Online Dating Stories

Sure, plenty of people have found love on the Internet. Some find promiscuous flings. Some even end up getting married. This article isn't about those types of online dating stories. This is about those once in a life time circumstances, when the person you meet online turns out to be a compete disaster of an experience, you know, once that "real life" thing kicks in.

Without further ado, I present the 10 most F-ed up online dating stories you've ever heard.

1. Quasimodo Needs Lovin' Too

Bobby Finstock from the Pointless Banter blog has had plenty of adventures in the online dating realm and fortunately for us readers, they almost always end up in disaster.

In one of ole Bobby's finest intimate encounters, he provides us with his hilarious night with a girl/it that he dug up from the Adult Friend Finder site.

"When we got to the restaurant my “date” got of the car and walked liked Quasimodo half bent over. One of her legs was severely longer than the other, giving her a very interesting gait. We went into the restaurant and ate, while the conversation was good all I could think about was that she was freaking me out a little bit."

Read the Full Story

2. Your 7th Grade Teacher

So, there you are filtering through a bunch of skeevy emails from a bunch of skeevy dudes all thanks to a prank. This is what happens when your best friend decides to post a casual encounters ad for you on CraigsList. Well this exact story happened to one girl and what she found was pictures of her 7th grade middle school teacher in her inbox. Yea it was awkward when she called him out on it, but after he offered to send her MORE pictures, then it just turned out-right F'ed up!

3. So... What's Your Sign Again?

While perusing the Plenty of Fish forums (always interesting) I found this little gem of an online dating story:

"The saddest (therefore, worst since I find all women nice in some twisted way) was a woman who showed me her X-rays on the first date. And I offered to take her to the hospital the next day, and then to a doctor's office not far from the hospital. She had terminal cancer. I doubt if she is still alive. I suppose I was the last guy who treated her to Chinese take-out."

Yikes! Talk about a weird situation. Not that I'm making light of Cancer or anything, but man that's one hell of a first date to deal with.

4. Missed Connection or Just Missed?

This little tidbit I found on the You Suck at Craigslist blog, which is hilarious by the way. It's not exactly an Internet dating story, really more of an Internet dating fantasy. Because really, what's worse than a creepy guy sending messages on an online dating site than a creepy guy who fantasizes about dating then posts it online?

Read the blog post here.

5. The Handicapped Hater

E from Geek's Dream Girl shares one of her weirdest online dating stories. The guy is pretty normal at first but then he drops a prejudicial bomb on her. Nope, he's not racist, not homophobic, he's anti-handicapped.

"Now, I can understand hating racists, rude people, the willingly ignorant… but the handicapped have no choice in the matter. You choose to be racist. You choose to be willingly ignorant. You don’t choose to be an amputee."

Read the Full Story.

6. You Want Me to Drink What?!

Like the previous story, this guy turned out to be pretty normal at first, even offered to buy the gal a plane ticket to come visit him. Every thing went great on their dinner date, which eventually lead to kissing, and then to the bedroom. Unfortunately this is where things started to go downhill. Apparently the guy turned out to be a self-righteous douche-bag and the night ended with the following:

"Then he says, 'you know what, if you can do this little thing for me we will work out and you can have all the credit cards you want. DRINK MY PEE, baby.'"

Read the Full Story.

7. The Shark Attack Girl

The video speaks for itself.

8. Well, We're Not Blood Related...

So you meet a real nice girl online, you have great chats, she has a sparkling personality and for some weird reason you get along like you were family. Oh yea, did I mention neither of the two parties had pictures on their profiles... so you can imagine the awkward moment when you go out on your first date to meet your sister!

Now granted she was only his step sister but that's still a little weird, right? Well apparently she was into it!

Read the Full Story.

9. Would You Like Some HIV in Your Coffee?

This one is just truly scary. Imagine that you've found the love of your life through an online dating site. You are really sure she's THE one. You finally fly across the Atlantic to meet her when upon your arrival, you find out that the love of your life is really a level 9 psychotic bitch. Here's what this poor sap had to deal with:

"I found a note on the kitchen table saying that she wanted me out of her house and if I didn't get out by midday she was going to call the cops. This is even though I had been cleaning her dust infested apartment and looking after her daughter. Next to this note she had also left another note which horrified me. She claimed she was HIV positive and that she'd been putting her blood in my milk and food."

Read the Full Story

10. You Got the Right Stuff, Baby...

Jami from Date Wrecks has tons of ridiculous online dating stories but this one really takes the cake. Again, this guy starts out to be a completely normal nice guy in the beginning but by the end of the story you can't help but feel bad for how pathetic the guy is. Here is one text message she got from him after their third date:

“I want to turn into a metal monster and pierce you with a drill penis killing you and having to assimilate with me so we can be one.”

Wow, just wow!

As you might imagine, this sends up a major red flag. The worse part is that trying to get rid of the schmuck just makes things worse, to the point where he sings New Kids on the Block into her voice mail. The actual sound recording is in her post.

My summary isn't doing this any justice, just go read the full shit show right now.


If anyone can beat these 10 stories then please post your messed up online date in the comments or shoot me a link to the article.


  1. Oh Matthew. Get it right! :)

    It was after the THIRD date, not the FIRST.

    If it was after the first date, we'd be calling it the ONLY date because there would not have been any others!

    Thanks for the plug.


  2. @Jami,

    Opps, sorry about that, I fixed it:)

  3. OMG.. the exact reason why I'm not into online dating. 6, 9, and 10 are uber f*cked up. I have dated a few guys I met online, but nothing disastrous like that. Holy crap.

  4. @Raivyn,
    Yea those one are totally messed up and luckily are pretty much out of the ordinary. If there were too many stories like this I think I'd have to give up on online dating as well.

  5. OMG. All of these stories are so horrifying. This one isn't as bad, but in the days of newspaper personals, my brother once corresponded with a stewardess/part-time model (she was in the Victoria's Secret catalog). Because of her flight schedule, they talked for weeks without ever meeting up. Then he gets a call from "her friend," saying that she died in a car crash and the friend would like to meet him because she knew how important he was to her friend in her final weeks.

    The "friend," of course, had a voice that was remarkably similar to the stewardess's. My brother told her to never call him again or else he'd call the police.

    Bizarre. Though not nearly as bad as any of these.

  6. Anonymous9:17 AM

    I met someone on Plenty of Fish. I proceeded to date this man who appeared to be completely normal, fun, exciting and romantic. As a few dates went on I notice some major mood swings, memory loss and disappearing acts on the weekends to visit his brother. Then after sometime he stayed over night at my house. He started acting completely off the wall. He proceeded to tell me he took 3 Ambien and tried to stay awake to see what all the hype was about. He started to tell me he was into Lucid Dreaming and set his watch to wake him up all night long which helps with accomplishing theses Lucid Dreams. At one point in the night he started to tell me that there was a little girl in the room watching us and who was she? The he started to tell me how he tried to kill himself with his gun but missed his head.Then he pulls out a lunchbag of meds that he currently takes. So many I lost count. Explaining what each one is for. How he functions at a really good job is beyond me. I would have been dead. It just got even more and more creepy as the night went on. After I tried to remove him from my life he will continue to contact you and wessel himself back into your life crying that you are his only friend and that he is not on drugs, not on dating web-sites, and how much he cares about you. Well after more research this person has an active profile on Match and is currently active on many meetup.com single events also. I want to warn the women of Tampa Bay to be very alert to this GQ man who is way to good to be true and be very careful.


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