People Share The Worst Date They’ve Ever Been On

People Share The Worst Date They’ve Ever Been On

unnamed-file.hdepositphotos @AntonioGuillemF

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

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

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

85. I Unknowingly Dated My Cousin

85-luis_molinero.jpgFreepik @luis_molinero

I was asked out by a cute coworker who was from a neighboring town. The date was incredible! He was smart, funny, and probably the most attractive guy I’ve ever met. When he dropped me off, he was kind enough to come inside to meet my parents. My grandma happened to be there and said, ‘Eric, it’s so great to see you, I just had coffee with your mom.’

Me: “Grandma, how do you know Eric?” Grandma: “Sweetheart. He’s your cousin.” After that, we hung out as friends and swore we’d never tell anyone at work that we totally dodged a bullet.

84. She’s a Spy!

84-nicoletaionescu.jpgdepositphotos @nicoletaionescu

I 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.

83. I’m Dating A Witch!

35-1.jpgPixabay (Victoria_Art)

I met this drop-dead gorgeous girl at the mall and mustered up the courage to ask her out (I’m usually a pretty shy guy). So we’re sitting at bar at a local restaurant, and she informs me that she is a witch, and that she had made her last boyfriend love her by casting a spell on him. She was even nice enough to tell me how the spell works, “I took a vial of my period blood and poured it into his wine, and tricked him into drinking it.”

“Now he’s mine forever,” she told me. She went on to say that it turned out she didn’t really love him, but because of her spell, he would love her forever. She claimed he was still desperately in love with her even though she had dumped him.

82. She Still Wears Diapers And Proud!

29-atlascompany-2.jpgFreepik @atlascompany

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.


81. The One Who Was NOT As Good As Advertised

21-stockking.jpgFreepik @stockking

I met a girl online, but she didn’t have any pictures of herself. She described herself as a 24-year old blonde with blue eyes and an “athletic build.” I really wanted to see her so I asked her out. I even let her choose the place so she would feel special.

I arrived at the restaurant with a big smile on my face, but I soon found out this “blonde bombshell” was actually 47-years-old and had three children with three different men. Needless to say we never talked again and I no longer find dates online.

80. #1 Tip To Meet Younger Girls

Matthew-Henry-from-Burst.jpgBurst (Matthew Henry)

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 entrée 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.

79. When Your Nails Attracts Him More


I was on a Tinder date with this guy and he was super awkward. It was weird. He tried to hold my hand and noticed I had acrylic nails on. So he picks up my hand and says “they’re so sharp like a cat…. scratch me.”  And he insisted I do it, so I just scratched the back of his hand and quickly made my escape.

Immediately after the date, I spent 20 minutes complaining via Chat App about how bad the date was. I thought I was talking to my friend with the same name as my date. It was my date and not my friend. I felt bad about it for weeks.

78. The ‘Prepared’ Man

78-nick-linnen-VbJRsn2yb34-unsplash.jpgUnsplash @Nick Linnen

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.”

77. He Wanted A Reimbursement For His Drink

20-8photo.jpgFreepik @8photo

Over coffee, he told me he was married but that his wife was “flexible.” He acted genuinely surprised that this wasn’t fine with me. It was really awkward.

The next day I told him I wasn’t interested in seeing him anymore, then he asked me for a refund of the drink I offered to pay for but he insisted on buying.

76. Oh, Baby!

41-benzoix-business-concept-portrait-handsome-handsome-business-man-suit-smiling-siting-work-office-with-serious-depressed-expression-isolated-white-background-copy-space.jpgFreepik @benzoix

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.


75. Do You Believe In Dinosaurs?

75-mego-studio.jpgFreepik @mego-studio

I met a guy online and agreed to meet somewhere. When talking about weird things that we believed in he proceeded to tell me dinosaurs are still alive and walk beneath the earth and that’s what causes earthquake.

He was dead serious too. He was very confused why I didn’t want to see him again.

74. Mr. Touchy Guy

74-ArtPhoto_studio.jpgFreepik @ArtPhoto_studio

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???’

73. Some Men Talk Too Much on Dates

73-jcomp.jpgFreepik @jcomp

Meet a guy from an online dating site. He seemed nice, but never stopped talking. After interrupting me for the 3rd or 4th time, I finally ask him “Do you want to hear anything I have to say?” He apologized profusely, said “You’re right, I’m so sorry!” and pulls out a pad of paper and a pen.

He then jots notes as I’m telling him about myself and whatnot. I finally ask him what he’s doing and he says “Oh, I’m writing down things I want to tell you when it’s my turn to talk again.”

72. The Machete Man

72-cookie_studio.jpgFreepik @cookie_studio

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!

71. Dating with Roaches

71-erik-karits-xvMYnYBHKF4-unsplash.jpgUnsplash @Erik Karits

Went out a bunch of times with this awesome girl I met through a friend. Smart, strong opinions and a pretty cool free way of thinking and living. She wanted to show me a place where she used to go to drink and dance. So we did. We arrived there, sat and asked for beers.

Five minutes in, I feel something on my back. I slap it with my hand and looked at the ground.. It was a Cockroach! Two minutes later, there is a cockroach going up her leg to which she yelled, but we kept drinking. Suddenly we look around and there are cockroaches going up the walls and tables of everyone. It was like a invasion. The cockroaches were everywhere. Every hole, every possible space on the ground. Disgusting.

70. She’s Perfect, Except..

70-8photo.jpgFreepik @8photo

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.


69. Aliens, aliens, aliens!

38-wayhomestudio.jpgFreepik @wayhomestudio

Dating is never easy but it’s even more difficult when you wind up on a date with someone who believes in aliens and only wants to talk about their alien obsession all night.

He said that when it rains, it’s because the aliens are sad, and if there’s a thunder and lightning, it means that aliens are really mad or just bowling. Let’s just say I was really happy when the bar closed.

68. I’m DEERly Scared

68-stockking.jpgFreepik @stockking

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.

67. The Unknown Girl

67-wayhomestudio.jpgFreepik @wayhomestudio

I met a girl for a blind date once. She seemed a little flustered at first, and I thought that was a little weird. She didn’t say a single word throughout dinner, finished her meal and walked out. I then checked my phone and there was a message from the girl saying she couldn’t make it tonight.

Who the heck did I just eat with?!!

66. I’m Dating With A Chinchilla, Too!

66-pexels-bulat-khamitov-4547060.jpgPexels @Bulat Khamitov

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.

65. What A Nice Plan You Got There!

65-wayhomestudio.jpgFreepik @wayhomestudio

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.

64. First Date Disaster

64-master1305.jpgFreepik @master1305

I’m a big strong guy but I’m also a baby when it comes to horror films and such. However this girl wanted to go see a horror movie as our first date and I was willing to act tough. I tried but I just couldn’t handle jump-scares. I’m fine with disgusting things, but don’t you try to scare me. Long story short, a jump-scare happened and I spilled a good portion of my cola onto her white shirt.

For a moment, I hoped that I would just apologize and few weeks later we would just laugh about it and have it as our cute story. Well, she had a different opinion, she changed seats, finished the movie, let me drive her home without saying a word and didn’t respond to my texts anymore.


63. Thanks But No Thanks!

63-wayhomestudio.jpgFreepik @wayhomestudio

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.

62. That’s Cringeworthy, Girl

62-drobotdean.jpgFreepik @drobotdean

Once, I met a girl through Tinder, and she was beautiful and interesting. She was a background actress. As I approached where we were meeting up, she called me to ask if I was on my way and explained that she asked to meet here just in case I was a serial killer or something.

Then during the date, she started calling me her boyfriend, and at the end of the date she told me she loved me and that I was an angel sent by God to her. Maybe it’s not funny, but it was definitely cringe-worthy. We actually dated for a few weeks.. What? I said she was beautiful.

61. She’s A ‘Fortune’ Teller

61-teksomolika.jpgFreepik @teksomolika

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.

60. Get The Food Out Of Your Teeth, Please?

2-cookie_studio.jpgFreepik @cookie_studio

I went on a blind date a couple of months ago and the guy was totally lovely, really friendly and likable. The only bad thing is that he had pieces of food stuck between his teeth the whole time and I don’t have the courage to tell it to him.

This doesn’t seem too big of a deal, but trust me, there was a LOT of food in there. It was un-natural. It got really awkward, very quickly and I just couldn’t get past it.

59. ‘Nothing’ Turns Him On

59-pexels-kimona-2280926.jpgPexels @Kimona

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!

58. Abort Mission! She Has A Boyfriend!

58-senivpetro.jpgFreepik @senivpetro

A friend of mine set me up with a girl he knew. She was cute, funny, smart, everything you hope for in a blind first date. After spending a good part of the day with her, we end up at this frozen yogurt spot. We talk for a bit and she mentions how much fun she had today. Then she says how much her boyfriend would like this spot and that we should all hang out next week.

I didn’t see that coming. I searched her on Facebook after the “date” and found out that she had been dating this dude for a couple years. Yes, she did indeed have a boyfriend. Never asked that friend to set me up ever again.

57. Mansplaining At Its Finest

57-drobotdean.jpgFreepik @drobotdean

My Date and I went to dinner. He comments on me ordering pizza in an Italian restaurant. He comments on me eating pizza with knife and fork. He comments on me not wearing enough make-up. I politely ask about his work. He explains what he does as if he’s talking to a 4 year old, even though he knows I’m getting two master degrees and already have a degree in Biology.

Throughout the date, he kept explaining stuff to me as if I’m in kindergarten. Doesn’t ask anything about me and goes on long monologues about himself. I decline getting another drink and leave. Dodge his kiss and give him a peck on the cheek instead. On my way home, I get a text asking if I’m sure I don’t want a kiss.

56. An Unexpected “Meet The Dad” Moment

34-cookie_studio.jpgFreepik @cookie_studio

Met a girl in a bar. Bought her a drink. Agreed to meet again. I went to her house to pick her up and take her to the movies. During the movie, she kept looking at the person behind her.

Turns out, it was her Dad sitting behind us the entire time with an angry-look. He then yelled at me and asked “What the F- do you want with my daughter?!” I quickly left and renamed her number as DO NOT ANSWER.

55. The Date that Ended Before It Started

55-raphael-lovaski-DEuob2v77wI-unsplash.jpgUnsplash (Raphael Lovaski)

Not actually a date, but it was the worst pre-date ever. So I met this guy online, and he asked me if I like heels and when I said yes, he then asked if I would wear them to our date along with high-waist jeans, full face of makeup, and lip gloss like “he likes.”

It wasn’t a big deal until he followed up with “Are you gonna look good for me? If not, then forget about me. You aren’t worth my time.” Ok then, date cancelled!

54. She Just Need “A Little Help”

54-cookie_studio.jpgFreepik @cookie_studio

The time I met my date at her place and she started talking about making a “donation” to help her out with rent and so on. She was even nice enough to point out where the closest ATM was.  She also made it abundantly clear that she WAS NOT a “working girl” and simply needed “a little help.”

Nope, nope, nope, nope. BIG-TIME pass baby-doll. As I left, I started to wonder how many guys she’d done that to and how much money she’s secured from those dummies.

53. My Pyramid Scheme “Date”


Met a guy via an online dating site. He corresponded with me daily for weeks and seemed pretty interested. After few weeks of chatting everyday, he invited me to hang out. It was our first date so I made sure that I look presentable from head to foot. I spent hours just to look beautiful so he will not be disappointed.

When I walk in to the door, I was like OK, maybe this is some kinda party/kick back and I’m just early. So I sit down. Then he turned the TV on and it actually turned out to be a MLM/Pyramid Scheme recruitment meeting.

52. I Unknowingly Dated A Guy With A Girlfriend

52-wayhomestudio.jpgFreepik @wayhomestudio

There was this guy who always messaged me how much he liked me. He asked me out on a date. I was single so I agreed. Long story short, I ended up having to pay the whole tab (cause he forgot his card) and drive. Ok, no problem.

Then during the movie, his girlfriend found my Instagram and messaged me telling me how they been dating for 3 years & he always does things like this. I was shook! I immediately got up and left.

51. Strip Club On First Date? Nah!

51-emiliano-vittoriosi-TTei7WkL4bE-unsplash.jpgUnsplash (Emiliano Vittoriosi)

I was out on a date with a guy who said he had no money because he forgot to bring his wallet and borrowed $10 to buy a drink at a convenient store.

He came back with a scratch-off, won $60 and took me home since I wouldn’t go to the strip club with “his winnings.” To make things worse, he didn’t give my $10 back.

50. He Let Me Pay For Everything!

59-Drazen-Zigic.jpgFreepik @Drazen Zigic

I once went on a date with a guy, and while we were driving to dinner we got a speeding ticket. He asked me to pay for the ticket, because I was distracting him, and then took me to dinner where he made me foot the bill.

After that he took me to a nightclub, where he told me about other girls he brought there. I made him take me home shortly after that and told him to forget my number.

49. The Best Gentleman Ever!

55-cookie_studio.jpgFreepik @cookie_studio

I hadn’t seen the guy in years, but we’d had a few dates back in the day and stayed friends on Facebook. I’d just been dumped so when he asked me to go for a drink, I said yes. We were only meant to have a quick coffee but he immediately launched into a rant about how terrible his life was now. He’d recently broken his leg, which got infected. There was pus, and showed it to me. It was rancid and smelled awful.

Then he made me go to a store with him to help him carry his groceries. Needless to say I wish I’d never met up with him.

48. She Walked Out After Seeing Me

48-cookie_studio.jpgFreepik @cookie_studio

So I met this girl on the internet and she seemed really nice and down-to-earth. We had a lot in common including our hobbies and politics and stuff like that, so I was thinking we might hit it off.

We agree to meet up in person at Coffee place. Now bear in mind that I’m not super attractive so up to this point she hasn’t seen any pictures of me, instead we have pre-arranged recognition signals. She walks in the door and I spot her by her clothing instantly, and start waving. She gets this sort of uncertain look on her face and walks over and says ‘Sam?’ and when I say yes she just says, ‘Haha.. No!’ and walks out. It felt pretty bad.

47. He Had His Own “Appointments”


Went to the zoo with a guy, we rushed through it and he wouldn’t let me see much of anything because he had a hair appointment he just had to keep. He was getting his remaining hair “frosted” which I thought was very weird. Does he think he’s in a boy band from 15 years ago?

Second and last date, he left me sitting alone at a table in the park for around a half an hour because he saw a tree he simply “had” to meditate under. Alone. No longer dating men with frosted tips.

46. Mind Your Date, Not Your Phone

46-wayhomestudio.jpgFreepik @wayhomestudio

I met this girl online and asked her out. She suggested that we should go bowling and that it would be very fun! So I went and picked the girl up, and took her to a bowling alley. She was texting the entire time we were there. She said her sister texted her that their puppy barked for the first time and she’s just asking for a video of the puppy barking, and that I should wait.

Cool I can respect that. But when I have to spend more than an hour with someone I barely know and I can’t talk with you for more than 10 seconds without you looking at your phone, it’s really bad. Also, we weren’t able to bowl because she wanted to go home to see their puppy barking in person.

45. I’m Done Paying Your Cab Fare. Bye!

45-mrsiraphol.jpgFreepik @mrsiraphol

I’d been on two dates with this guy that I’d met online. When we first started speaking, I initially thought that I had hit the jackpot: he had immaculate grammar when texting, was really good-looking and seemed totally perfect. We got on really well during our first date, and I didn’t even mind when he insisted that we take turns buying drinks.

But then when it was time to leave, I ordered a Taxi to take me home, and he got in, asking if he could share the taxi (even though we live nowhere near each other). When we pulled up to his flat, he jumped out without offering to pay for his fare. At first, I wasn’t that put off – until the same thing happened on date number two! I mean, I’m all for going Dutch, but when I’m having to pay for YOUR cab home – boy bye.

44. “Do you think this girl is right for you?”

44-wayhomestudio.jpgFreepik @wayhomestudio

On our three-hour drive to a food and wine festival, I stopped for food, leaving my phone in the car with my date. My cousin texted me, ‘Do you think this girl is right for you?’

My date took my phone, read the message and asked the same question in an angry tone. I was so put off by the invasion of my privacy I was just honest and said that she probably wasn’t. The next three hours in the car, we drove in absolute silence.

43. He Is Feeling Himself Too Much

43-drobotdean.jpgFreepik @drobotdean

A guy I met online who was so full of himself, there was no room for me at the table. He asked me if I liked his watch, then told me it was a $20,000 birthday gift to himself. He also told me he could pleasure himself better than any woman could.

At one point, he even asked the elderly women sitting next to us if we made an attractive couple. They said yes. His response? “That’s right ladies, you can buy me online!” I was so embarrassed, apologized to them, and said he was right—you can buy any kind of crap online.

42. A Date In The ER with Michael Jackson

42-wavebreakmedia_micro.jpgFreepik @wavebreakmedia_micro

So my date shows up with a friend who is dressed like Michael Jackson. On our way to the car, his friend drops a bottle & a shard of glass pops into my date’s eye. Cut to the Emergency Room. Me and his friend are in the waiting room.

After like 20 minutes of waiting, his friend gets up and proceeds to put on a full concert of Michael Jackson tunes. It was the most confusing 4 hours of my life.

41. Slow Down It’s Our First Date

41-drobotdean.jpgFreepik @drobotdean

I went on a first date with a guy and he asked me what temple I wanted to get married in, my two favorite colors and my favorite season.  Then we went to the mall before our movie and he went ring shopping and bought a ring for our wedding.

The date lasted SIX HOURS and I did not know what to do to stop it. Then, when he took me back home, and said “Please don’t forget to text me tonight about your dream wedding so we can plan it next week.” I’m done with online dating now.

40. What Just Happened?

39-scott-rodgerson-ffH_GkINfyY-unsplash.jpgUnsplash (Scott R.)

I had a great date I met on and I was walking her home at the end of the night and suddenly she started to run away. I started to chase after her and asked her what happened and she just said “Police! I have a warrant out for me.”

Well, when I found out she had a warrant I kept running, but in a different direction than she went. I eventually got caught by the cops and I had to spend a good 20 minutes explaining to them the situation and how I was in no way involved in her illegal doings.

39. CinDUIrella Is That You?

39-nakaridore.jpgFreepik @nakaridore

Got set up on a blind date once from mutual friends. She shows up to the restaurant already a little tipsy, orders multiple appetizers, and only takes like one or two bites from each one. Then she proceeds to order more drinks and is visibly drunk at this point. She gets up and says she’s going to the bathroom and staggers off.

About 15–20 minutes go by, so I try to call her several times, but no answer. Finally I decide to pay the check and just leave. About two hours later, I’m sitting at home and I get a call from an unknown number. It’s the police department. She was picked up on a DUI on her way home after she ditched me and gave the cops my number to see if I could go bail her out!

38. The Liars

38-cookie_studio.jpgFreepik @cookie_studio

When I was in college — many years ago, before the advancement of cellphones and social media — I was chatting with a girl I met on a [bulletin board system] who lived in Long Island, New York. I was 18 at the time but lied and said I was 22 because she said she was 25. We spent a few weeks emailing each other as well as calling each other. We even exchanged pics. When we finally met up, things blew up.

Turns out we both lied about our ages. She was really 33 and lied because she thought she looked younger. She admitted she sent a college photo of herself to me. We still had dinner together, but it was awkward as hell. We never spoke again.

37. “We,” Not “I”

37-master1305.jpgFreepik @master1305

Showed up to a Tinder date where we agreed to meet, but she wasn’t there. Texted, and she replied back that ‘they’ were around the corner. Come to find she (a mid-20s divorced socialite) and her friend (a mid-40s man) had been drinking all day and were pretty drunk.

I proceeded to join them at the table, where she proceeded to talk about the married guy at the next table over and kept walking by and dropping things so she could bend over in front of him.  And then they decided, mercifully, to ditch me because I was no fun.

36. Like A Movie

36-8photo.jpgFreepik @8photo

Met her for dinner. We seemed to hit it off well in the first few minutes, until I started feeling the worst pain ever in my side. Turns out I had a kidney stone. I unfortunately had to leave very quickly. She then blocked me via text when I abruptly left dinner, so she never got the message that I ended up in the hospital.

I didn’t see her for years until we ran into each other at a bar, me with a different girlfriend, her with her husband. I explained what had happened; she felt pretty bad, but hey, no long-lasting harm done. I bought her and her husband a drink, chatted for a few, and left them to finish their evening together.

35. The Smell…

35-cookie_studio.jpgFreepik @cookie_studio

I was told we were going to dinner and then shopping. I drove to his town, one hour each way, cuz he didn’t have a license. He directed me (didn’t know my way around at all) to…Burger King. I ended up paying for dinner, too. Then we went to…Walmart — where his mom worked — so he could get a discount. Didn’t buy anything.

On the drive home, he started apologizing out of nowhere. I thought it was because of the bad date. Until the smell hit me. He passed gas and I had to legit pull over and roll the windows down a while.

34. She Can Do It Herself

34-diana.grytsku.jpgFreepik @diana.grytsku

I got set up on a blind date by some friends. The date was early September and we met in a restaurant in the city. It was a nice place, the kind where the waitstaff wear dress shirts, ties, etc. I was in a nice suit and tie; she showed up in jeans, flip-flops, and a hoodie.

I jokingly said something along the lines of, “I’m assuming they didn’t tell you this place is sort of snooty?” She goes, “They did. I didn’t give a dang. I ain’t shaving my legs and putting on some fancy dress for some guy who I don’t even know if I want to even touch his weenie, let alone if I’m willing to let him between my legs.” I just stared at her in disbelief. She then said, “I mean, you seem nice and all. But I ain’t in the mood to do all that work when I can just go home and do it myself.”

33. “I’m Just A Hugger”

33-kues1.jpgFreepik @kues1

I was on a tinder date and we met at a bar. She was a bit late so I have sample of their whiskey selection. Anyways 10 minutes later a girl comes towards me and I reach out for a hug, she looks a bit confused but hugs me nonetheless. As we stop hugging two things happen simultaneously. #1 my Tinderdate arrives, and we lock eyes. #2 The waiter, still in my arms, tells me they just changed shifts and she will be my server this evening.

My anxiety kicks it into high gear and I am barely able to fathom what’s going on much less explain to either of them what’s going on.

32. Psycho Alert!

32-nakaridore-1.jpgFreepik @nakaridore

I met a guy at a concert who asked me out to dinner the next weekend. Said we’d go to a restaurant halfway between his place and mine. Gives me the address which I printed out on Mapquest bc this was before GPS was normal on phones or in cars. I get there and it’s an apartment building. Call him to say I think he gave me the wrong address and he said, nope! You’re driving. Takes me to an Applebee’s because they have the cheapest happy hour he said. We have one drink and he eats potato wedges by himself.

When I drove him back, he asked me where my overnight bag was. I said I’m not staying the night and thanks for the beverage. He took my keys out of my ignition and told me to go upstairs. I told him if he doesn’t give me my keys back, I will start screaming and call the cops. He threw them in the front seat as he got out telling me I’m missing out on hot tub time. I thankfully never saw him again.

31. Love At First Shart

31-atlascompany.jpgFreepik @atlascompany

A guy approached me at a coffee shop and we ended up hitting it off and talking all night. About a week later we had our first “real date” at my place so I could cook him dinner. I lived in a small one bedroom apartment at the time and the bathroom door was right next to the kitchen. He excused himself before dinner and proceeded to take the loudest, and what I presumed to be, the most massive poop this universe has ever seen. The sounds of the toilet carnage still echo in my nightmares. I of course didn’t mention that I heard the whole event and we went about our evening.

After dinner we got into my bed so we could watch a movie. 30 minutes into it, I needed to use the restroom, so I got out of the bed to reveal that I had unknowingly started my period and left a noticeable pool of blood where I was sitting. He helped me change the sheets. Anyway, we’ve been married a year now and he still takes the nastiest dumps known to mankind.

30. A Budget Date

30-rawpixel.jpgFreepik @rawpixel

I went on a date with this dude who asked me out. We’re seated, he sees the prices of the menu and goes “this is too expensive,” waits for the free water and stuff they give out, takes the free stuff and is like “Ok, let’s go somewhere else.” I have no choice so whatever.

He then takes me to another restaurant, and told me I couldn’t order anything more than $10 off the menu. I couldn’t believe it so I stopped talking to him and left. He then walks ahead of me and doesn’t even check to see if I’m safe.

29. You Had Fun, Really?

29-wayhomestudio.jpgFreepik @wayhomestudio

I ordered a steak for lunch and he tells me I shouldn’t be eating steak, I should get a salad so I don’t get fat. Freakin’ serious? Then we went across the street to a bar where he totally ignored me and started talking to a guy about baseball. Like, COMPLETELY ignored me.

So I grabbed my keys and said, ‘I’ve got to use the bathroom, I’ll be right back,’ and Irish goodbye’d him. The next day he texted me, “I had fun. We should go out again sometime.” LIKE YOU DIDN’T NOTICE I WENT TO THE BATHROOM AND NEVER CAME BACK!?!?

28. I Just Wanted To Have Coffee?

28-user18526052.jpgFreepik @user18526052

I recently signed up for a dating site and had my first date. Let’s just call her Caitlyn, she seemed nice enough, and attractive, but on the actual date all she wanted to discuss was politics. She was discussing politics the whole time, like non-stop, and I don’t even have the chance to talk.

I have nothing against anyone interested in politics, I’m just not into debating national policy on a first date.

27. “She’s Not Even That Pretty”

27-gpointstudio.jpgFreepik @gpointstudio

It was a blind date and to my surprise, he was kinda cute. We talked about random stuff, and everything went fine until his phone kept ringing. I told him to answer the call, maybe it’s something important. He said no worries, it’s just his ex-girlfriend.

After like 10 missed calls, he finally answered and then ended the call with “She’s not even that pretty” and “I love you too.”

26. A Sisterly Match

26-wayhomestudio.jpgFreepik @wayhomestudio

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.

25. Wrong Sent Messages Isn’t Bad At All

25-adem-ay-ik_AuIWeBBM-unsplash.jpgUnsplash @Adem Ay

I’d only met someone from Tinder once (he was a bouncer at a club). First of all, he showed up to our date unfashionably late by 30 minutes. He apologized, gave me some bogus excuse and we ordered our food.

While waiting, he checks his phone and he accidentally texted me something along the lines of “Sorry babe, I’m at church so I will be late” then had the nerve to say he meant to send it to his sister.

24. Hands Off My Pizza!

24-wayhomestudio.jpgFreepik @wayhomestudio

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.

23. I’ll Take An Assist On That!

23-drobotdean.jpgFreepik @drobotdean

So there was this really sweet girl I had been interested in but I was too afraid to ask out. One day, I finally had the guts to ask her out. Surprisingly, she said YES! The next day, we went out to eat. I was so ashamed when I realized I forgot my wallet. So she paid for me.

Then we went to a party at a mutual friend’s house where I got mistakenly got black-out drunk and passed out. My buddy was at that party and now the two have them have been dating for 3 years. Still don’t know what happened that night.

22. They Want “Threesome”

40-cookie_studio-1.jpgFreepik @cookie_studio

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.

21. What A Coincidence

21-standret.jpgFreepik @standret

In college, a friend of mine set me up on a blind date. I wasn’t in a great mood at that time because I had received a traffic ticket a few hours before.

When I arrived at the meeting place, my day got worse when my blind date turned out to be the cop who gave me the ticket. I immediately left him and never respond to his messages again.

20. “I Bleed For You”

20-wayhomestudio.jpgFreepik @wayhomestudio

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.”

19. Puppy Trumpet

19-stockking.jpgFreepik @stockking

I met a guy online and we went to the movies on our first date. At the end of the night acted like he was going in for a kiss, but instead he put his whole mouth over my nose and blew into it.

He laughed so hard and said he does this to his dogs and calls it a “puppy trumpet.” After that date, I never contact him again.

18. The Mighty Man

72-cookie_studio.jpgFreepik @cookie_studio

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?

17. He Wanted to Show Me His Pee Trick!

2-user3802032.jpgFreepik @user3802032

A guy took me to dinner but forgot to make reservations, so we couldn’t get a table. He then suggested that we should go to a different place where he proceeds to drink way too much.

On the our way home, he asks me to get out two stops before my actual station to watch him pee into the train tracks.

16. No Teeth, Dust and Everything Not Nice!

16-cookie_studio.jpgFreepik @cookie_studio

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. He Gave Me a Poop Soup

15-wayhomestudio.jpgFreepik @wayhomestudio

I once went on a date with a guy who spilled a giant cup of ice water all over me at the restaurant. After dinner we go to my place so I can change into dry clothes. He uses my bathroom. After taking way too long he asked me through the door for some towels — he clogged my toilet with his manturds and then got his poop soup all over my bathroom floor.

Oh, and I realized at one point he was wearing a toupee because he’s balding, which he was super weirdly sensitive about.

14. Slow Down, Girl!

14-cookie_studio.jpgFreepik @cookie_studio

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’).

13. The Killer Smile

13-8photo.jpgFreepik @8photo

We’d matched on Tinder and arranged to meet. We’d chatted a fair bit and he seemed like a nice guy and pretty funny, but we’d not gone as far as exchanging Facebook names or Instagram. Looking back, this was my first rookie mistake.

We went to dinner – never a good move on a first date as it takes a minimum of an hour and a half – but I still turned up excited to meet him. So we finally met. He smiled at me and I was completely taken aback – he had no teeth! I awkwardly sat through one very hurried course before rushing home to check his Tinder profile again. He hadn’t been smiling with his mouth open in any of them.

12. 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.

11. The Guy With A Secret Hole

11-wayhomestudio.jpgFreepik @wayhomestudio

Met a guy who grabbed my hands and looked me dead in the eyes. Told me he had to tell me something so I wouldn’t freak if things got serious. He then proceeded to tell me how they screwed up his Circumcision. That he had two holes in the skin under the head that you could fit a pen into.

I don’t know if it was like you could fit in one hole and out the other or two separate holes the size of a pen.  I’ve wondered for years. How did he know a pen would fit unless he stuck one in. I was too blindsided at the time to ask. Never talked to him again.

10. Marry for Green Card?

10-freepic.diller.jpgFreepik @freepic.diller

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!”

9. “You’re Much Prettier Than His Girlfriend”

9-8photo.jpgFreepik @8photo

I went on a date with this guy I met at a party. He invited me to wedding reception, and I said yes of course. When we arrived at the place, his relatives were there including his parents, and introduced me to them. Then his mom told me “You’re much prettier than his girlfriend.”

It was the only time I’ve ever thought about faking a phone call and pretend that there’s an “emergency” so I can leave.

8. What The Hell Man?!

8-mego-studio.jpgFreepik @mego-studio

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.

7. The Epic First Date Fart

7-atlascompany.jpgFreepik @atlascompany

It was my third week of college and I really hit it off with this girl in one of my classes. We decided to meet up for dinner one night in the middle of the week. I got there a few minutes before she did, and when she came in and sat down, she farted really loud. Like unavoidably loud. She excused herself to go to the bathroom and never came back.

I’m now a senior in college. I’ve seen her around campus a bunch over the years and we haven’t talked since that day.

6. There’s “Forever” in Dating

6-nensuria.jpgFreepik @nensuria

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.

5. This Guy Offered Me “His Seed” On Our First Date


A few years ago I went on a date with a retired athlete. I was 27 at the time and didn’t have any children. For some reason he thought this was weird and told me that something must be wrong with me if no guy had given me their seed by now. He went on and on about my “biological clock ticking.”

I remained silent the whole time because I didn’t know how to react. After a minute of awkward silence, he asked me if I was ovulating because he’d be willing to give me a child if I need. I’m happy to say we never spoke again after that miserable date.

4. “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.

3.  He’s asking a Different Mode of Payment


I went out for dinner and a movie with a guy. I tried to chip in money during both, but he insisted that he cover it all. At the end of the night, we’re sitting in his car in the parking lot of the restaurant we had just eaten at, and he asked me to touch his “down there” and said “I mean, I bought you dinner and took you to a movie, it’s the least you can do.”

Thankfully I lived nearby, I hopped out and walked home.

2. Pull Over Poop

2-senivpetro.jpgFreepik @senivpetro

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…

1. This Guy Was Definitely On Something

1-creatista.jpgdepositphotos @creatista

It was a blind date. We met up at a coffee shop close to our university. He was definitely under the influence of something, and it was hard to get a normal conversation going. He just kept telling me I was as beautiful as the brick wall we were sitting next to, and that my skin looked soft enough to be made into a nice silky robe.

It was really weird and awkward, so I excused myself for the bathroom and decided to just leave him (including the bill). The date lasted a maximum of 10 minutes and that was the worst and longest 10 minutes of my life.