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15 Unbelievable Dating Nightmares: Internet Stranger Stories

The rise of online dating has revolutionized the way people meet potential partners, but beneath its surface lies a disturbing reality. Hidden behind attractive profiles and seemingly genuine conversations, there exists a dark underbelly of deception and manipulation. The anonymity provided by the internet allows individuals to craft intricate facades, concealing their true intentions and motives.

Fake Everything

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One user shared, “I Dated a guy who was arrested on our date by detectives. He tried to return a pair of fake Gucci sunglasses. When the store clerk threatened to call the police, he flashed an FBI badge to the clerk. It turns out they got him on tape flashing what actually was his brother-in-law’s FBI business card. Did I mention he WAS the school principal for a reputable Catholic school in my area? The story made headlines and all.”

Substance Abuse Issues

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A second user said, “I met a girl in West Hollywood, and we went to dinner. She turned out to be way bigger than her pictures, insanely rich, was Ozzie Osborn’s cardiologist’s daughter or something like that, and had a nasty coke habit. The whole date she was doing cocaine in the bathroom and barely ate her food, and then afterward, we went back to her place, where she visibly spiked my drink with a Mickey and then asked me to tie her up, and then refused to allow me to drive my car out of her garage, leaving me to wait in my car all night until the morning when I followed someone out. “

Wizard Of Wet Pants

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A third user added, “I met a guy for a walk-and-talk through my favorite park. We had a nice vibe online, and I hoped we’d have a good time even if we weren’t attracted. He was completely bizarre. Spent a lot of time trying to get me to believe that he was some sort of psychic or wizard with magic powers, asked for a ride to the bus station from the park(I had no idea he hadn’t driven himself there) and suddenly he had to pee during the 5-minute drive. Wet his pants just before getting out of the car.”

A Brief Date

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A commenter shared, “I met up with a girl from OkCupid whose photo was nothing like her in real life (in a bad way). On the date, she spent about an hour telling me how she falls out with her friends all the time and generally being self-obsessed and uninteresting. I felt no connection/spark and was polite but said that I didn’t want to see her again, made my excuses, and left. 2 minutes after leaving, she texted me saying that she had never met anyone like me and thought we had something special, I politely replied and let her know I didn’t want to see her again, and she kept texting me. I kept ignoring her to try and send the message. However, a couple of weeks later, she sends me a string of abusive messages ‘Why are all guys the same.’

Bad But Somehow Good

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This poster recalled, “I went out with this guy, and it was beyond awkward. Nothing to talk about, nothing in common, no spark or connection whatsoever. Ends with a polite hug and some generic “that was fun, bye.” I figured the date was so bad neither of us would contact each other. He posted on Facebook that he just had the best day of his life, blah blah, happiness, and rainbows. So I had to go through the awkward, telling him I didn’t feel it. Then there was the hateful “girls are awful” status update. How can two people perceive a date so differently?”

Great Game

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Someone shared, “Went on a date with a Navy boy. He seemed smart and sweet online. He picks me up in this incredibly ostentatious yellow Camaro, which I have the sneaking suspicion he borrowed as it was a stick, and the dude had a helluva time driving it. We decide to walk on the boardwalk for a while, so he pulls into a parking garage. In his attempt to park the car, he completely sideswipes the car next to us – leaving yellow paint all across their car. He acted like nothing happened, so I said, ‘Umm, I think you may have hit the car next to us.’ He gets out, looks at it, then climbs back in and goes, ‘I guess we should park somewhere else,” and peels out before I could even say anything. Fast forward, the date is going poorly (as a hit and run is never a good start), and it’s miserably hot out, so we decide to see a movie. It happened to be a kid’s movie. He has his feet on the seats in front of us, which is no big deal until a dad holding his toddler daughter comes in, and the only seats still open are the ones in front of us. The dad goes to sit down – Navy boy doesn’t move his feet. He even moves his feet forward a bit so that he hits the dad in the head. The dad looks back at us, and Navy boy sighs heavily, takes his feet down, looks at me, and goes, ‘My feet were there first.’ After the movie, he asked if I wanted to go to dinner. I said no, and he drops me off (I’m surprised he didn’t drop the transmission as well…) and asked when he could see me again.”

Throw Up Throw Out

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A top-liked comment said, “We went out and got sushi, it was really awkward, he was awkward, I was awkward. Sparks were not flying. After dinner, I wanted to bolt. I casually said I would walk to my friend’s apartment because they lived nearby. He goes, “Okay, great, that sounds like fun!” and came with me to my friend’s place. I know, I should’ve clarified that I meant I was leaving, but I didn’t want to hurt his feelings. We ended up having a few drinks at my friend’s place, and my friend and I said how we planned to go to this bar for karaoke. Again, he assumes we meant all together.

They Go Out Drinking…

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We go, we’re all drinking, he gets kind of plastered. Eventually, my friend and I decided we were going to bounce. We all drove together, so he came back with us. So my friend and I are sitting in her living room, he goes into the bathroom, and we hear him all out hurling. He was in there for TWO HOURS throwing up. I kept knocking and asking if I could call him a cab, but he kept saying he was fine.

Eventually, my friend tells him he has to leave. I walk him out to the front porch and ask again if I can call him a cab. He says no, leans in as if he’s going to kiss me, seems to think better of it, and then says he hopes he can see me again soon.”


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This poster commented, “I met a woman for a date, wasn’t a lot of chemistry, but she worked two interesting jobs, and there were no real warning signs. She invited me for a second date to this picnic campout where she didn’t know the people very well.  We talk about how most of her friends are guys, and most of mine are girls. She says she is bringing  “a crew” along.

The crew turns out to be another guy and 2 dogs. I engage the guy. He is super friendly and nice and spends time fetching things for her and playing with children. We know some of the same people. After about 5 hours, I’m sitting alone with her, and ask, “How long have you known Tim?”  She responds, “Oh, I met him through OkCupid 3 months ago. He’s going through a divorce, and he’s not sure if he is going to have his kids or not, and I don’t want to date anyone with children.”


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A user said, “I met up with a girl who was using her daughter’s photos for herself, saying she was 25 online but was really 55, and said she had no ethical problems lying online as long as she told the truth while in person. To top it off, she was on her third marriage and had multiple Facebook accounts.”

A Therapy Session

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A poster recalled, “I talked to this guy online for a couple of days, and when we realized we have the same favorite bar, he invited me out for a drink at that bar. He was late. I started to get annoyed, but when he showed up, I soon learned that his photos did not do him justice. He was so incredibly hot. He bought me a drink, and we started talking. After a few drinks, he offered to walk me home, I knew where it was going, and I was ok with it.

I brought him to my room, and he sat on my bed. I sat next to him and it was awkward and quiet. He noticed my glasses on the nightstand and put them on my face. He stared at me for a second, then climbed on top of me and kissed me.

Just weird kissing, then he said, “Do you think it’s weird I wouldn’t touch you until you had your glasses on? I love glasses.” He then kept making really fake faces while we got undressed, and right when I decided it was too weird and that I should make him leave, he finished prematurely.

He freaked out, and I told him it was ok, and we got dressed. He got under the covers and got really quiet and serious. I didn’t know what to do. I didn’t want him there. He told me he was just using me. Got me drunk, got me home, wouldn’t leave, and now I’d have to hear him get his problems out. Finally, I told him to go and walked him to the door. He kissed me on the forehead and walked backward down my hallway, staring at me until he reached the stairs.”

Mass Texting to See Who’s In to Party

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This person shared, “There was a guy I never actually met because I got a super creepy vibe from him, but he would send out mass texts regularly asking if I wanted to do anything that night. I could tell it was a mass text because it showed the numbers of everybody else he was texting on my iPhone. Him: Hey, want to do anything tonight? Me: Can you please remove me from this mass text list? I’ve never even met you. Him: This isn’t a mass text, lol. Me: (Screenshot where it lists everybody else he’s texting) Him: Oh, lol. You caught me. Random Stranger: Yeah, we can all read this. Me: Yeah, bye.”

The Fun Committee

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One user shared, “We went on one date. He would not stop talking about his “gorgeous” ex-wife. Also mentioned being a lawyer, his huge house, and he’d gotten around he’d been since his divorce about a million times. He was very self-absorbed and clearly just looking for hookups. Texted me the next day: Him: The fun committee is meeting at my house tonight. Me: The fun committee? Him: Yeah, you and I are the only members. Me: …”

Germ Transfer

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A top-liked comment said, “I met a guy on Craigslist. After talking to him on the phone for a few weeks, we decided to meet up at his place for our first date—the 2nd bedroom in his apartment was a shrine to his dead grandparents. Since they raised him, it must be his way of remembering them, so I let it go. We date for a few months, and it just so happens he demands we take showers and sleep buff every night so as not to “contaminate” the bed sheets. I got out of bed for a glass of water once and got yelled at for 30 minutes about how I brought germs from the living room into the bedroom.

The whole relationship was like something out of the twilight zone. We broke up shortly after he demanded my mother sign a letter saying she would respect his wishes not to meet her and have it notarized. The scariest thing about this is that he’s an NYPD officer, not exactly who I want out there protecting the streets.”

Angry Dater

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“So, I had been talking to this guy over OkCupid. He lived about two hours from me and decided to take a trip to meet me. I wasn’t opposed to it. When he got here, he looked NOTHING like his photos. He was 5’3/4 (his profile said he was 5’7). He was pudgy (his profile said he was “thin”). He had super crooked teeth. He was just…rather unattractive. Either way, I was still willing to give him a chance. I’m not that shallow. He brought a bottle of wine…

The Lunch Date

We went out to lunch, which was nice, and then hung out at my apartment. I had maybe… half a glass of wine. He finished the entire rest of the bottle (This was well before 4 PM). The next thing I know, he’s begging me to make out with him. I gave it a go for a minute before becoming really turned off and stopping. I just wasn’t feeling it. He then started complaining that he was tired and drunk and wanted to sleep. I told him he was welcome to crash on my couch for the evening.

He asked if he could sleep in my bed. I said that’d be ok and I’d sleep on the couch, then. I guess he just wanted to sleep with me because the next thing I knew, he was yelling, throwing a total hissy fit, and storming out of my apartment to drive back to where he came from.

Whale Of A Catch

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Finally, a poster responded, “This was back in the days of Myspace-style top-down private photos. I saw this cute girl in her pictures and connected online, and decided to meet up. I waited for her at a designated spot in a mall, then got a call. She says, “I think I can see you. Is that you in front of the store?” I was trying to look all over for her, but there was a big girl in my way, so I said, “I can’t see you; are you behind that huge lady”? ..silence.. then it hits me that the big lady was her. But to defend my shallowness, this girl was close to 300 and had misleading photos. Needless to say, it was an awkward date.”

Source: Reddit

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