People Share Stories of Their Worst Online Dating Experiences


The online dating world is very tricky business. With the rise of dating apps like Tinder, Bumble and Hitch, things just got a lot more complicated.

You may have had some on some great online dating experiences in your life, but for every good one, you probably have had five awful ones. Thinking back on all those horribly awkward interactions can be a scary prospect, so we figured that best way to get over them is to replace those memories with the hilarious stories of other peoples horrible online dating experiences.

So, in the name of mental health repair, we ask people to share stories of their worst online experiences of their lives. Some of these are absolutely ridiculous.

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1. A Sisterly Match


I’m talking to this beautiful, cool girl, and we eventually make plans to meet at a local pub. I show up and it turns out it’s my younger sister.

We had both apparently made fake profiles.

2. ‘Nothing’ turns him on


Met a guy, chatted, he seemed relatively normal. We go for our first date in a pub. A well-lit pub. We’re having a couple drinks, talking and whatnot, I see his hands under the table, moving around. It cannot be. OH BUT IT IS. He was touching himself. Apparently I was turning him on too much (I did absolutely nothing but sit there) and he couldn’t help himself. Date ended pretty quickly after that.

The followup is, when I got home he’d sent me an epically long email about how I was fat and ugly and a tease. Oh, and ended it with the phrase, “Don’t bother responding, because I will not read it.” Done and done!


3. She’s a ‘Fortune’ Teller


Tinder. We matched and had similar experiences and had the same sense of humor. She was very nice and really caring online. We met somewhere with my friends (which I did mention, and she agreed). Everything went well until –  she started reading palms, and telling everyone they were going to have miscarriages and abortions.

I really made the mistake of taking her out around my friends.


4. Hands off my Pizza!


This woman seemed really cool. We were both 25. She was fit, witty, and had piercings. We meet. Well, fit was apparently 5 years prior, but she was “trying to get back to her normal weight” and so thought it appropriate to use the older photos. I’m talking a 85lb difference from photo to reality. Okay, well her nose ring is actually a weirdly shiny wart that she tries to pass off as a nose ring because she’s embarrassed by it.

All of this isn’t the worst part though. We were out for dinner and went to a decent gourmet pizza joint. Low lights, thin crusts, and wine. Without asking, she reaches over and starts picking toppings of my pizza. Pardon me, but keep your damn hands off my prosciutto! It was unforgivable.


5. Thanks but No Thanks!


I got a message from a girl on PlentyOfFish who was a solid 9.5 – we spoke for a bit and decided to meet up at the bar. We had a drink and she revealed how she was a model and how she needed money for rent.

By the end of drink 2, she had proposed “herself” for rent money. I said thanks but no thanks and left.

6. They want “Threesome”


My first time going on a date arranged on OkCupid. I had been texting this girl for a good three weeks and we finally decided to go out on a date. I suggest we go to dinner and a movie at a restaurant closer to her place so she can walk/bus and I can do all the commuting. It takes me an hour to drive there and I arrive at the restaurant before she does a good thirty minutes before our date so I could be prepared.

The waitress brings her to my table and I see another man walking with her. They both sit down and at this point I’m really confused. She introduces me to her husband and he tells me that they’ve been looking for another man to join them because his wife likes “threesome” and he’s into it as well. For the first time in my entire life I was completely speechless. I had no idea how to reply so I just got up and walked out of the restaurant without saying a word.


7. I’m dating with a Chinchilla too!


We met at a local pub for a few drinks, and we got chicken fingers. The conversation was terrible, but I noticed she was taking the chicken fingers and ripping them up in her hands and putting the breading in her huge purse. So naturally I called her out on it.

She smiled and said, ‘Oh, I’m just feeding Sammy,’ and pulled out a fat chinchilla from her purse. She plopped the thing in the middle of the table, and it just kinda chilled out. I played with the chinchilla a bit, and she kinda got mad at me for playing with it and back in the purse it went.


8. “I bleed for you.”


We met online, and he seemed cool and funny. We went out a few times. A few weeks in, he told me I was almost perfect, except my upper arms were fat. I think he meant it as a compliment.

When I didn’t want to go on a second date, he sent me a photo of him cutting himself with blood everywhere titled, ‘I bleed for you.’


9. What a Nice Plan you got there!


We met online and had been talking for a while when he asked for a first date. Fast forward – during our dinner, he proceeded to tell the waiter that he was going to get me pregnant that very night.

I pulled $20 out of my wallet to cover my half, and ran out of there.


10. I’m DEERly Scared


I got to know a nice girl on OKCupid for a few weeks before we decided to meet up for a hiking date. She only wanted to communicate through email or the dating site -which I thought was odd but just went with it. 30 mins into our date I found out why. She’s married and her husband is a jealous, gun collecting hunter type who she’s thinking about leaving.

For 90 minutes – I felt like a deer during hunting season on that hike. Every bush movement and twig snap I was sure was him. Screw her for not coming clean before hand.


11. The Mighty Man


I met this guy online and agreed to meet up. As I was walking with this dude and he was boasting about how strong he was. Then he turned to me and said he could attack me in a second and there would be nothing I could do to stop him.

Oh… Sorry… Was that the part where I was supposed to be impressed?


12. She’s Perfect, Except..


Met a girl from PlentyOfFish, we were to meet for drinks at a bar. I hate being late so I arrived about 15 minutes early and ordered a beer. When she walks through the door, I literally choked on my drink. Very pretty girl just like her photos suggested but failed to mention she was 8 months pregnant. Her excuse was she must have forgotten to mention it. I apologize and leave.

She sent me a text the next day to ask if she could borrow some money.


13. The Machete Man


After a few OkCupid attempts I ended up dating a guy a few times. Eventually he asked if I’d like to see his flat and I said yes. He had loads of swords and machetes on the wall and decided to hold one to my throat to show me how incredibly strong they were.

So yeah there was that!


14. No Teeth, Dust and Everything not Nice!


Started talking to a guy. He was nice and had a few pictures up. Not overly handsome, but very nice and that goes a long way in my book. We agree to a date and since he lived by the restaurant we were headed to, I agreed to meet him at his place. I get there and he steps outside and smiles revealing that he had absolutely no teeth in his mouth. Okay, he still was a nice guy.

He asks if I want to come in while he finishes getting ready. I walk into a nightmare. Everything was covered in at least an inch of dust, grime and garbages. He asks me if I’d like to have a seat (on his couch that had become a brownish-grey from the years of filth build up and cigarette smoke) I say no thanks, I’ll just stand. He excuses himself to go finish getting ready.

I texted my friend and told her to call me right away with a story about car trouble. Deleted my profile that night and have never tried online dating again.


15. Mr. Touchy Guy


The guy was immediately sort of creepy – though he seemed perfectly normal via email of course – but I’d traveled a good 45 minutes to get there, so I figured I’d at least watch the movie with him and pay for my own ticket. He had this weird look in his eyes that screamed “awkward 27-year-old that has never seen a boob and is creepily close to his mother.” I sat down with him, and he put his hand on my leg. I moved his hand away. He put it back on my leg. I moved it away again.

Later on in the movie, he put his hand back on my leg but his fingers moved to my inner thigh. I very quickly moved his hand and told him to not touch me again or I’d get up and leave. He just sort of chuckled and rolled his eyes and put his hand back on my leg. I slapped his hand away, stormed out of the theater, and he followed right after me going ‘What? What??? What’d I do???’


16. Slow Down, Girl!


Met up with a girl from OkCupid over coffee. She was a couple years older than me but she seemed nice. Two minutes into casual warm-up conversation, she starts talking about her ex(s) and how she would stalk them at random at their work places.

By the time I get her off this topic, she’s moved on to me and talking about our perfect life together, how she’d secure our love, started demanding passwords to my Facebook and Email. I walked out shortly into this, and she made a grab for my keys (had’m out as part of the ‘I’m leaving’).


17. Oh baby!


This woman messaged me, and I usually don’t date women with children, but she said that she had one 4-year old boy, and she seemed nice, so I thought that it was worth the price of dinner to meet someone new. Well, we set up a day and time for our first date. I drive over and meet her at the restaurant. I notice that she’s struggling with something in the back seat of her car. I walk over to greet her, and she says “Can you help me with this?” I look into the backseat of the car, and there’s a newborn in a baby seat. I awkwardly reach into the backseat and pick up the baby seat. I carry the baby/baby seat into the restaurant and give my name for the reservation.

Come to find out that she gave birth 2 weeks ago, and she didn’t tell me about it, because she was embarrassed that I wouldn’t want to meet her. She was in a relationship with a dude that left her when she came up pregnant. She was a very nice girl and we still talk, but I made it clear that although I understand her reasoning, that it wasn’t exactly fair to me to spring this newborn on me at our first date. and then after I didn’t bolt from the restaurant (as much as I wanted to), proceed to ask if I would consider adopting the baby “if we work out”. I did tell her that it would be a good start for her to update her match profile, stating that she has TWO children now. It’s sorta a joke between us now.


18. The General’s Daughter


So I’m currently in the military overseas and I got bored one day so I got on OkCupid thinking, you know what screw it why not. So I’m on the site just messaging a few random girls and start talking to this girl that seemed pretty nice.

Well we hit it off and decided to grab dinner one day. During the dinner I not only found out she only just turned 20 (which really isn’t that big of a deal) but she was also the daughter of one of the Chiefs on my ship. I kind of just noped out of there.


19. The ‘Prepared’ Man


Guy turned up for a date in person after online chatting. We didn’t hit it off, so to end the night politely and early. I walked him to the rail station so he could get the train home.

En route, conversation went dry so I randomly asked, “So. What’s in the backpack?” He answered: “Oh that’s my overnight bag. If you were my type you never know, I may have needed it.”


20. Marry for Green Card?


I  was speaking to this guy on Tinder, and after only a few minutes he asked me if I would marry him for $10,000. No joke. Apparently he was a foreigner and wanted to become an American citizen. He couldn’t comprehend why I declined. He said, “Other people would do it for half the money!”

I was like, “Not me, hun!”


21. #1 Tip to meet Younger Girls


Chatted to guy online for about a week, then agreed to chat on phone and eventually arranged to meet for dinner. I did not recognize him, he was bald in person (in his profile he had hair and said he was 25), he was closer to 50 now. Sat down ordered a entree as a main, chatted pleasantly and told him it was not going to work as he had misrepresent himself and flat out lied to me. He became angry and said that’s why he had to have a younger profile or younger girls wouldn’t be interested.

I just got up and left.


22. What the Hell Man?!


I was using and talked to this guy for a bit before agreeing to a date. He insisted on being a gentleman and picking me up from my house. I didn’t think much of it and agreed. We go to dinner, and almost immediately he starts telling me how much he hates tattoos (I have a small one on my wrist) and that he saw I was Conservative leaning and hated that. I asked him if he wanted to end the date early since we weren’t a good match but he said no, we should finish eating, so we kept eating in total silence.

He then says he’s not ready to end the night and wants to go somewhere where we can talk more and decides on his office building. I’m a people pleaser and was stuck with no car so I went. We walk into the totally dark, empty building, and he starts muttering to himself and kind of laughing, “What the hell, man. What the hell are you thinking…” and tells me we’re leaving and going somewhere else. I freaked out by now and doesn’t know where he’s driving me. He drives for like 30 min in dead silence up into the mountains outside town and suddenly pulls the car off the road. After minutes of silence, he does that nervous laugh again and says to himself, “Wh-what the hell are you thinking man. You cant do this…” He then says he’s taking me home and does.


23. There’s “Forever” in Dating


I joined OkCupid four years ago hoping to hook up with a bunch of girls. I spent a week messaging a few girls and decided to meet the first of these girls to put my plan into action. We ended up hitting it off and started dating exclusively.

Four years later, and we are still dating. She completely ruined my plan.


24. She still wears diapers and Proud!


I was on OKCupid last year. Went on a date with a girl that seemed really cool. She played guitar and was really into photography. The date was great until she told me that she still wets the bed, still wears diapers, and wearing diapers and pretending to be a bad little girl was her thing. She also wanted me to come over and take naughty baby photos of her for her FetLife profile.

I deleted my account as soon as I got home.


25. Nope, not again!


I went on one of the dating sites and filled out all of their forms and personality tests. I was only looking someone to talk to and maybe go more than that if things will go well. So I’ve filled it all out and it gives me my top match – My ex wife who had left me out of the blue 3 weeks previously.

Thank you Internet!


26. “I will just pay you to spend time with me”


Got a random message from a guy on PlentyOfFish. He seemed nice and we messaged back and forth like once or twice. Then everything changed. He told me that the pictures weren’t him and that he wasn’t 21 (my age). He was actually 48. (Ew.) He then said something along the lines of “I have a lot of money. I will just pay you to spend time with me. Please. You’re beautiful and funny and you seem like a lot of fun.”

It was so creepy. I deleted my account after that.


27. Hey, Mr. Filthy!


I joined OkCupid and I met this guy. He showed up thirty minutes late, annoying but not a huge deal. His hands were covered in filth though, like black dirt and not just a little, pretty much covering his entire hands. He has mismatched socks. I had a hard time sitting next to him and tried to talk the entire time because his breath was so awful.

I lied and told him a had to wake up early so I could leave after the first beer.


28. Yikes!


I was once talking to this guy online and after a few hours of nice, PG conversation, he did a complete 180. He asked where I worked because I looked familiar. He said I looked like a girl from an amateur adult video.

I’ve never been so thankful for the block button in my life.


29. The ‘Full of Questions’ Guy


When I first started using dating apps, I often made the mistake of agreeing to dinner on a first date. Like with this guy. On our date, the guy asked: ’Do you believe in God?’ ’What do you want to name your kids?’ ’How many surgeries have you had?’ — all unprompted, and all before the appetizers had arrived.

I don’t think I’ve ever ordered and eaten tapas so fast in my life, just in hopes to hurry and get the hell out of there. The guy was relentless throughout the meal. ’Aren’t those the same pants you wore in one of your profile pics?’ (they were). ’When was the last time you got your hair cut?’ (ummm… ) ’How are you still single?’ (because I keep agreeing to dates with weirdos like you.) When the date ended and we stood up to leave, he of course ended with the classic, disappointed question: ’Oh. How tall are you?’


30. She’s a Spy!


Went on a date with a girl I met online who said that she was looking for “anything”. She asked me out for dinner. When we arrived at the restaurant, she doesn’t order anything.

All through dinner, she was staring at another couple in the restaurant. She had found out where her ex-boyfriend was out with his new girlfriend and booked us a table there for the same time just to spy on them.

31. She’s Fangirling Kardashians


Met a girl on OKCupid. We agreed to meet at an outdoor bar along the boardwalk, and then go the carnival. Shorts, slippers, t-shirt sort of thing. I thought it’d be a great first date, no pressure and lots of fun. She shows up at the bar looking like she’s heading to the Grammy’s. High heels, heavy make up, dress, and 50lbs heavier than she looked in her photos. She didn’t want to go the beach bar, instead, she wanted to go an expensive Italian restaurant that was down the street. She bought the most expensive entrée (lobster), got to 2 glasses of champagne, and a slice of cake. When the bill came, she excused herself to go the bathroom (the bill was $75, $60 of which was from her order). I paid the bill like a gentleman but was extremely turned off.

During our conversation, I learned that: One. She still lived with her parents. Two. Her Mercedes Benz was the center of her life, the one that her parents bought her. Three. She was unemployed and never had a job in her life. Four. The only news she paid attention to was the Kardashians.


32. She Stood Me Up and Meet my Friend


Got stood up at a cafe. She called and told me an emergency had come up ad she wasn’t going to make it. I had only been waiting for 3 or 4 minutes, and wasn’t too upset about it, so i called a friend to see what he was doing.

Ended up meeting him across town at the bar he was drinking at, where he introduced me to my date he had just met playing pool there.


33. “I can’t believe you’re a real human!”


Met another guy from OKCupid. He knowingly used pictures that didn’t accurately reflect the way he looked and kept saying “You look just like your pics!” in shock, along with “I can’t believe you’re a real human!”

Like what do you expect? A robot?


34. That’s not a good idea, Big guy.


So I was talking to this guy, seemed nice enough (he had only posted a face shot) and he asked me to buy me dinner. Ok sure. When we met he was easily clearing over 450 pounds. Not really into that but I stuck it out because he seemed like a nice person. We get coffee first, and then walked over to the restaurant. Now, I’m no athlete but I do like to hike and rough woods camp. I may not be winning any marathons but I can walk for miles. This poor dude was wheezing within 20 feet of walking. Clearly it was an effort for him. I felt bad for the guy, and I try to be open minded but I can’t date someone that unhealthy.

We get to the restaurant and he tells me about himself and his life. He told me he was a dom and started to imply we could go make out later and he would top me. I said I had to leave after dinner and scooted as soon as it was polite to do so.


35. She Wanted Fair and Square


We seemed to connect pretty well online. We met at a restaurant, ordered our food. Everything is going well until she weighed her food. She literally brought an electronic scale in her purse to dinner. Put it on the table and weighed her portions.

We were sharing so she did this three times as she made a new plate for herself.


36. Pull Over Poop


I met this girl from OkCupid. Her profile picture was cute and asked her on a movie date. She chose the time of the movie and what time I was picking her up. About 10 minutes from picking a girl up she asked me to ‘pull over’ to the side of the road, I don’t know why. She got out of my car on a sort of busy highway street and proceeded to poop in front of my car.

When my brain registered what was going on I leaned over closed the passenger door and drove away…


37. What a Fantastic Compliment!


One of my first dates from OK Cupid. Met him for lunch during a weekday. His first comment to me was that I looked professional and not like the party-girl he was expecting. He spent the entire lunch bragging about how good he was at his job and how “jacked” he was from his workout regiments. Then he mentioned he lived with his brother. I told him that was nice and asked him if they were close. His answer: “Yeah, well I felt like I had to take him in. He was never quite the same after our mother was murdered”.

To cap off the experience, On the way out of the restaurant he honored me with this fantastic compliment: “I just wanted to let you know I had a great time with you. You are officially #2 on my list of girls that I’m considering dating. Hopefully you can rise to #1 by the next date.”


38. Being Ignored


I went on a date with a girl from OkCupid. It was about 9 p.m., and she sent me a message out of the blue. We talked for a while, and she wanted to meet up with food. I hadn’t had dinner yet, so I agreed. We were to meet up at a local diner. She was about 5′ 2″ and somewhere between 190-210lbs.  That would have even been OK, but it wasn’t just her. She had brought her friend (with a toddler) along. Oh, and her friend brought another friend. So here I am with 3 girls and a toddler that I don’t know. All three of the girls had brought Monster energy into the restaurant with them.

We sat down at the table and it just went downhill from there. The toddler ran out of juice in her sippy cup, so the mom filled it with monster. She then let the toddler play with the sugar container. She promptly poured sugar all over the table and started licking it up. Meanwhile, all the girls are laughing at the toddler and having a great time. They’re talking amongst each other and not even attempting to include me in the conversation. After about 5 minutes of them ignoring me, they started talking about guys from high school. Long story short, I ate half a chicken sandwich, excused myself, apologized to the waitress for the mess and the awful people, left a $50 and got the hell out.




Met someone from the Internet and didn’t recognize him due to him being about two feet shorter and ten years older than his profile (he is carrying an ornate gentleman’s cane too.) Once we were sat down with our coffee, he proceeded to open up his Trespass backpack and carefully remove a small chocolate muffin in a plastic wrapper. He peeled the plastic wrapper off the muffin whilst maintaining eye contact with me and not saying a single word.

Next out of the small front pocket of his backpack comes a little candle and a lighter. He placed the muffin in the middle of the table, stuck the candle in, lit it and began to sing at the top of his lungs “HAPPY BIRTHDAY TO YOUUUU…” After a few seconds of utter shock, other customers awkwardly joined in. Then he whispered to me, “Go on, make a wish”. Trying not to cry, I stared at the muffin, blew out the candle and wished to die but it did not happen.

There was not a second date. Also in case you were wondering, it was not my birthday.


40. Now that’s seriously awkward!


Met this girl in I asked to meet up and let the her choose the restaurant. She arrives 15 minutes late plus, at least 10 years older than her pic and 35 pounds heavier. LOVELY pics; in person, wow, not attractive. But I’m a gentleman and go forward as though all is fine, including letting her choose where to be seated. And where’s that? She asks to be placed where she can see the TV as she wanted to watch Melrose Place or some other awful TV show, I don’t recall.

As it turns out, I was happy to let her watch TV. We passed through the meal in relative silence. To add insult to injury? The best friend of my ex-wife turned out to be a waitress in said dump and swung by to give me a snide smile and hello. (She was laughing inside at my heifer of a date and I’m sure she passed along word.) Awful date.

Ariana Aufiero

Ariana Aufiero

I am an extremely verbal person who excels (and profusely enjoys) writing and/or talking about anything and everything! I love writing... Did I mention that?

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