16 Online Dating Stories So Freaky We Want to Quit the Internet

Wendy Robinson | May 18, 2016 Love & Sex

I've been married for nearly 11 years, and nothing makes me happier to be off the dating market than hearing the horror stories of my friends still out in the dating world. Most of my friends who are still looking for love -- or looking for the second time -- use online dating sites or apps. And nearly all of them have an example of an online love connection that turned out to be a total disaster.

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Dating is hard no matter how two people end up connecting, but when it's on the Internet -- well, people tend to let their freak flags fly. Or sometimes, worse, they don't show off how weird they can truly be. I know, I know, this is how love is found in the modern age. But some of the things my friends have told me about their online dates ... well, let's just say the word "horrifying" was used more than once. 

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Not to make light of another's plight, but one person's disaster is another person's entertainment. So, please enjoy these real-life stories of matches that seemed like a good idea on the computer screen but turned out to be ... well, not so hot.

Image via iStock.com/Martin Dimitrov

  • Flowers?

    1

    "One showed up with a dozen red roses; [I realized] upon further inspection they turned out to be from a gas station and made of panties. Among all my other reactions, a big one was, 'Who the hell wants 12 pairs of the same panties?!!'" -- G.K.

  • Bible Thumper

    2

    "I met a guy on Christian Mingle. Because I'm a Christian. We met up for our first date and he spent the entire time telling me I was in the wrong denomination and was going to hell if I didn't convert to his particular church. It was the longest cup of coffee in my life." -- S. T.

  • Tears at the Bar

    3

    "I was out with a guy who started crying at the bar while telling me about getting dumped by the woman he'd left his wife for. Then I had to drive him home. When I pulled up to his apartment building, he was like 'I don't suppose you want to come up?' Uh, let me think -- NOPE." -- O.B.

  • TMI Guy

    4

    "Once I opened with a standard 'How are you?' and he replied, 'Not good. Having a terrible day with my IBS.' He also spent 45 minutes telling me about battle reenactments he went to and called me an overprivileged idiot after asking my opinion on legalized drugs." -- K.U.

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  • Segway Felon

    5

    "I matched with a guy on Tinder. After exchanging a few messages back and forth, he asked if we could meet.

    I got to the restaurant a little before 8 p.m. and texted him to let him know where I was sitting. He responded that his meeting had run long and he would be about 15 minutes late. I played on my phone and nursed my beer, looking up every time the door opened to see if it was him. And then there he was, rolling into the restaurant on a Segway. And when I say 'into the restaurant,' I mean he rode this damn thing all the way over to our table.

    I should have just gotten the check at this point, but then I would have missed out on the rest of the amazing evening, which included him telling me that he didn't put any toxins into his body, including alcohol, and then glaring at my beer (my third one at this point). He also told me he had a hard time dating because he was a convicted felon and people googled his name and then never wanted to date him again. (PS -- I totally googled him when I got home. Turns out the story he told me about why he had been arrested was completely untrue, according to court records.)

    Finally, he told me about the major accident he had had a few years back which caused him to get the Segway (because he had to relearn how to walk). His dramatic retelling of this story included having me take an up-close look at his tracheotomy scar and feel the place on his leg where several steel rods had been installed. As we walked out of the restaurant (rather, I walked, and he Segwayed), I decided to make one last ditch effort to make the night memorable and asked if I could test-ride his Segway. He declined. I had been drinking, and it's unsafe to drive a Segway with so many 'toxins' in one's body. At this point, he goes in for a hug, and whispers in my ear, 'I'd really like to kiss you, but I've got the most wicked oral herpes outbreak.' I managed to get out of earshot of him before I started cackling." -- H.P.

  • Swipe Left

    6

    "I saw my boss on Tinder. Nope! Fastest swipe left of my life." -- K.L.

  • Walk Away

    7

    "I had been chatting and exchanging pictures with a guy for a few weeks when we decided to meet for a walk. I waited at the park for him and when he walked up to me, he looked me up and down and said, 'Yeah, I'm not into it' and walked away. Just walked away. I never heard from him again. Super good for my self-esteem." -- B.Z.

  • The Slur

    8

    "I teach special education and am passionate about my work and my kids. He kept using the 'R' word even when I asked him not to. What a jackass." -- E.D.

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  • The Unicorn

    9

    "I've learned the hard way that listing yourself as a bisexual on dating sites, you just get SO MANY threesome requests. I learned this after going on my first date when a guy showed up WITH HIS WIFE. He thought I was 'a unicorn' (a bi-woman who wants to get with a married couple). I'm not a unicorn." -- J. R.

  • Catfished

    10

    "I got catfished by my ex! He set up a fake dating profile and we started talking. I agreed to go a date with this guy and my ex showed up, begging for a second chance. It was deeply creepy. I'm off online dating forever now." -- H.G.

  • The Big Lie

    11

    "I went out on a date with a guy and when he showed up he weighed at least 150 pounds more than he did in any of his pictures. The thing is, I don't mind a bigger guy. But I just felt like he was either A) a liar or B) not comfortable with himself. Neither option was appealing." -- D.F.

  • Rude!

    12

    "I was on a first date -- like a real first date, my first with a woman after a lifetime of dating men. I was so nervous about exploring this part of myself and had been reluctant to take the plunge. But Kate seemed amazing. And she was. At first. And then we went out to dinner and she was so unbelievably rude to the waitstaff. The highlight was when she called the busboy a 'numb-nut mouth breather.' Yikes." -- J.W.

  • DTF?

    13

    "What broke me on online dating was the constant deluge of unsolicited dick pics and being asked if I want to have sex before even being asked my name. I'm not a prude but ENOUGH." -- R.T.

  • The Vampire

    14

    "His message informed me that he was a writer of Gothic erotic fantasy novels and was a vampire that 'feeds.' He was curious about BDSM and was a nymphomaniac with the right girl. I am not the right girl." -- B.M.

  • Short-Tempered

    15

    "My worst story is the guy who was 4' 8" and his photos didn't show that. Clearly had a height complex and was super aggressive. That being said, not too long after the short guy date, I met my husband on OkCupid. We've been married a year now." -- B.M.

  • Milkman

    16

    "One lazy Saturday morning, I got a message from a guy on OkCupid. His message was actually thoughtful and funny, unlike 90 percent of the messages I get, so I responded back. We messaged back and forth all morning, then he asked if I was free to meet him for lunch. We met an hour or so later, and I was really into him -- and I thought the feeling was mutual. After we finished eating, he asked if we could go do something else, but I was headed to a friend's wedding shower, so I told him I would call when it was over. 

    I met back up with him and we hung out the rest of the afternoon and night. At some point towards the end of the evening, he complimented my breasts, then asked a very unusual question -- 'Did you breastfeed your child?' I thought maybe he was going to say something like 'because it doesn't look like it, they're very perky' (wishful thinking), but instead when I said yes, he asked if I had ever produced milk since I stopped nursing, and would I be willing to take some pills he had ordered off the Internet to try and induce lactation because he had always dreamed of being able to nurse while having sex.

    I was fairly new to the online dating scene at that time and I seriously just did not know what to say. I think I just changed the subject and then left soon thereafter. He called me several times thereafter, but we never went out again." -- H.P.

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