How to be good at dating is one of the greatest mysteries in life, but one thing is clear—do not do what these people did. As awkward, uncomfortable, and disappointing as even an ordinary date can often be, some examples take “dating nightmare” to another level. From the shocking and disturbing to the absurd and hilarious, here are the worst dates that people have ever been on.
Worst Dates Of All Time
1. A Case of Mistaken Identity
A girl I know once reached out and asked if we could go on a date. I said sure. When she arrived at the date, she walked up to me, waved at me, left, and then called me. Apparently, she had put me in her phone as someone else and scheduled the date with me thinking I was that other person. We ate together anyway.
2. A Man of Many Interests
I went out with a guy from Tinder who turned out to be legitimately crazy. He regaled me with stories of how he assaulted police officers, burned his arm to impress girls, spent significant time in a psych ward, and lost his virginity to an overweight sex worker. He also told me that my eating disorder made him feel better about himself because it made me crazier than he was… He also told me I had obvious acne scars.
After our disaster date, he wouldn’t stop contacting me. He even went as far as asking me to stay in a rented house with him in another city. When I said no, he claimed I had ruined his entire year. I deleted Tinder immediately after that.
3. Not What She Signed Up For
I went on a date with my then-wife. After we ordered food, she said, “This isn’t really what I wanted.” I thought she meant the restaurant. Nope. She slid her wedding ring across the table and left. Her mom was waiting outside for her. I got home and the apartment was clear of all her things except the divorce papers.
4. Getting Grilled
I took a girl to a quiet bar and grill, ordered a beer, and then listened to her lecture me about how I am using beer to hide from my insecurities. It wasn’t long before I ordered a second and a third…
5. Quid Pro Quo
I went out for dinner and a movie with a guy one night. I tried to chip in money for both, but he insisted on covering 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, and he asks me to sleep with him. He says, “I mean, I bought you dinner and took you to a movie, so it’s the least you can do in return.”
Thankfully, I lived nearby. I hopped out of his car and walked home.
6. A Picture Is Worth a Thousand Sweaters
I went on a Tinder date with a guy who is now in my contacts as “DoNotAnswer NaughtyPic.” Prior to the date, he seemed normal—but I was in for a rude awakening. We texted and talked on the phone, then arranged to meet at a local restaurant. He was cute, but definitely bitter about something. He was from California and apparently didn’t like this new city we were in. He started talking about sex and complaining about how uptight everyone here apparently is about it.
In the middle of dinner, he invited the waitress to a party that his company was throwing. This was after sending back the French fries he ordered. I showed him a picture of my dog on my phone. He then took out his phone and showed me a picture of his private parts. We walked out of the restaurant together to get our cars from the valet. My car came first and I left.
He texted me later to let me know that he had my sweater. Apparently, I dropped it on the way out of the restaurant. He said that if I ever wanted to see it again, I would have to hang out with him. RIP, sweater.
7. The Afterparty
I once went on a date with someone who then hung out in my parking lot for two hours after she dropped me off, just in case I changed my mind about doing something after dinner.
8. Speaking His Mind
I once met a guy from OKCupid. He seemed nice, but never stopped talking. After he interrupted me for the third or fourth time, I finally asked him “Do you actually want to hear anything I have to say?” He apologized profusely and said, “You’re right, I’m so sorry!” He then pulled out a pad of paper and a pen, and proceeded to jot down notes as I was telling him about myself and whatnot. I finally asked him what he was doing.
He replied, “Oh, I’m just writing down things that I want to tell you when it’s my turn to talk again!”
9. It Bet This Date Was a Lot of Fun
Early college first date: She wanted to go to the horse-racing track for the day. When we arrived, she took me to her family’s box seats…and her family members were all there, waiting for us. She knew ahead of time that they’d be there, but didn’t tell me. It felt like an ambush. It was a very long, tedious day of races and betting, followed later by a seemingly endless dinner at her parents’ house…where they talked exclusively about gambling, horse-racing, and high-stakes betting.
I couldn’t wait to go home and get away from all of them.
10. It’s So Hard to Say Goodbye
I once went on a date with a girl who I met on a dating app. We decided not to talk at all before we met up, kinda like a real blind date would have gone before the internet. So, we were both excited and set up to meet at an old bar in the city. I got there early, and she arrived five minutes later. We talked for a bit and then she suggested we eat.
I wasn’t super hungry, but I got something anyway. She ordered about four drinks. During our conversation, we realized that we had a lot in common. We had even worked at the same place about a month apart! We also liked the same movies, music, etc. It was honestly an amazing night—but I never expected it to end how it did. At the end of the evening, I asked the waitress for the check.
While I was waiting for it to arrive, my date said that she needed to go to the bathroom. She then got up and walked straight out the door of the restaurant. Just right out the front door, adios. I went back to my phone to ask her why she did that, but she had already deleted her account. I’m not entirely convinced that she wasn’t just a very hungry ghost!
11. A Romantic Setting
He brought me to what turned out to be a strip club for our very first date. I was not impressed.
12. Taking a Scab At It
I once went on a blind date with a lady who wouldn’t stop picking at her scabs all night. She literally made a pile out of them on the restaurant table. I excused myself to use the washroom. When I came back, my soup was there but the pile of scabs wasn’t. No, I didn’t eat the soup…
13. Long Time No Speak!
I went out to dinner with a guy once. When we finished eating, we went back to my place and watched movies. He left at around two in the morning. Half an hour later, I got a call from him. He was asking me to come and bail him out of jail, because he got caught driving home while his license was suspended. Awesome…
14. When Age Isn’t Just a Number
I was volunteering at a university orientation market when we met. Cute girl, had a nice chat, set up a date. I think I was 22 or 23 years old at this time. When the day comes, I pick her up at her place. Turns out she lives with her mom. They have a rather childish argument in front of me about whether or not her bicycle lights are working, but alright. Moms will be moms, right?
We have dinner and talk about this and that. She tells me about her horse. I tell her about the time I tried horseback riding as a kid and we both laugh. She talks about an actor who she thinks is sooo cute. Instead of taking a walk downtown after dinner, we decide to go see the latest movie with that actor because why not. It’s kind of chilly out anyway.
During the intermission, we talk about music and she hasn’t heard of any of the bands that I listen to. I thought that was odd, because they were all fairly well-known. I ask her about the music she likes, and she mentions a whole bunch of current boy bands. I’m now starting to have a horrible hunch. I tentatively ask her a few more questions. Eventually, I give into my sinking feeling and ask her the fateful question: “How old are you?”
It turns out she’s fourteen. The guy behind us just about chokes on his popcorn as he realizes what’s happening. Turns out she wasn’t at the orientation market to find a program of study, she was just tagging along with her older sister whom I had never met or heard about. Perfectly lovely person, but I felt so stupid.
15. Dirty Dancing
I once accidentally pooped in my pants while on the way to the bathroom during a date. My underwear was ruined, so I threw them out and returned to dinner with nothing between my pants and my skin. I think it’s safe to say that this was my worst date of all time.
16. Not an Appropriate First Impression
I was once on a blind date with a guy. It was the first time that we had ever met each other. Within the first ten minutes of the date, he had made at least five wildly inappropriate and offensive jokes. When I acted shocked and confused, he insisted that I “lighten up.”
17. Lip Service
I once met a girl on Tinder, and we texted for about a good month. Then, one day, my parents were away on vacation so I finally convinced her to come over to my house to spend some time together. As soon as we started kissing, I somehow bit my lip and started bleeding uncontrollably. I had to go to the ER. She does not want to see me again.
18. He Finally Opened His Mouth, and That’s What Came Out??
My worst date ever was my first ever OKCupid date. The guy shows up still talking on his phone, looks me up and down, and then silently motions for us to go into the restaurant. It was a Lebanese place, but he immediately declared: “I don’t really like African food.” At this point, I was just waiting for my roommate to meet me outside later so I could tell her about this disaster—but it got even worse.
While I was waiting, he continued talking long enough to inform me that he had written a musical about historical tragedies. That’s normal…I also paid for dinner because, in his own words, he was a “feminist.” Ahhh, Brooklyn!
19. Weighing Her Options
I once went on a date with a wealthy, bigger woman who was used to always getting her way with men. We had become friendly over the past few weeks due to mutual friends and hanging out at social gatherings. She asked me to go drinking with her, so I said sure. When we got to this little hole in the wall bar, she introduced me to all her drinking friends.
I’m assuming they were the people who frequented this bar. Anyway, she started trying to aggressively make out with me at the table in front of her friends. I tried to tone things down, and she then started complaining about how shy I was being. After I told her that I didn’t feel comfortable, she decided, in front of the whole bar, to yell out, “HOW MUCH WEIGHT DO I NEED TO LOSE FOR YOU TO DATE ME??”
I quickly got the impression that I was no longer welcome at that bar. If everyone’s looks could kill, I would have died 100 times. I left quickly.
20. Mirror Mirror On the Wall
I once went out for a drink with a guy. Behind me was a mirror. Whenever I would begin to try and speak to him, he’d just look straight past me and shamelessly stare at himself in the mirror while making various faces.
21. The Kid in Me
My worst date was when we went to his house and he immediately turned on children’s shows. When I tried to speak, he aggressively shushed me.
22. Planning for the Future
I was really young, probably about 15 years old or so. I was boy-crazy. I had a crush on every guy who even remotely expressed an interest in me. That being said, this one guy…there are no words to describe this guy. His name was Jesse. We met through a mutual friend and, while he wasn’t exactly my type, he told me he thought I was pretty. I wanted to give him a chance—HUGE mistake.
A couple weeks later, we decided to meet up at the mall for our first official date. He was very sweet. We were holding hands. You know, typical teenage stuff. But then he got weird. VERY weird. We’re sitting on this bench, when he turns to me and stares at me right in the eyes before saying, “Wow, when I look at you and I look into your eyes, I feel like I’m looking into your soul.”
I’m fifteen and desperate for an epic love story at this point, so I just smile and let him continue. He goes on to say, “I know this seems soon but…I think you might be my soulmate. I can’t wait until the day we can get married, have babies, and live together. We’re going to have such an amazing life together!”
So let me recap. I’m fifteen years old, I’m on a FIRST DATE, and my date just essentially proposed to me. I got the heck out of there as fast as I could and never talked to him again.
23. Who Wants to Be a Loser?
I once was a “Phone a Friend” for a guy I knew who was on the game show Who Wants To Be A Millionaire. He asked me out on live TV before the question. I said yes, because who would turn down a guy who asked you out on TV? I got the answer wrong and he lost the game because of it. Nevertheless, I still had to go to dinner with him after that.
It was by far the most awkward and worst date ever.
24. Not Worth the Wait
My worst date was when the guy was more than three hours late. He was texting me telling me that he was 20 minutes away for two of those hours. As soon as he arrived, he tried to tell me to leave the part of the venue I had already paid for so that we could go where he wanted instead. He then tried to start a fight with a friend who I happened to run into and called my aunt a bunch of inappropriate names.
I just walked away from him after that last one, and we never spoke again.
25. A Tall Tale
My roommate once set me up with a guy who made it known that he was very irritated by the fact that I wore high heels on our date. Why? Because it made him feel smaller. Note: he was still taller than me by several inches, just less taller than he would have been otherwise.
26. Sister Act
I once went on a date with a girl who brought her sister along to chaperone. Awkward…
27. Manual Labor
Back in college, this really attractive girl in several of my classes started flirting with me, laughing at my jokes, asking me for help with the assignments, and complimenting me. After a few days, she asked what I was doing after class. She said that she needed to do a favor for her aunt, but that after that we could have dinner and “see what happens.” I was all over that.
I drove her to her aunt’s house to meet her. She introduced me to another guy who was already there and told him I was there to help. He showed me what we were doing, which was replacing a flight of stairs going up to her kitchen door (the ground floor was the garage and storage). I had never done anything like this before, but she was hot, so I was game. She disappeared as soon as we got started.
About 30 minutes in, we had the stairs assembled. It was a kit and the other guy knew what he was doing, so it didn’t take too long. We wrestled everything into place. We hadn’t spoken too much beyond instructions, so I eventually asked “So how do you know Julie?” thinking he was probably a cousin or something.
He responded with, “Oh, we’ve been dating for about a year.” I froze up, and he looked over at me. “Oh shoot, man! I’m so sorry! I thought you were just a friend from school. She’s done this before, but she promised me she’d stop.” He went on a little about how she likes to manipulate guys to prove she’s still “got it.” At one point, he said, “I’d leave her, but things in our bedroom are incredible!”
I made some remark about wanting to get revenge, and we both had a laugh over it. He was actually pretty cool about the whole thing and insisted that I take $60 from him for my time and effort. She came back with a bag of McDonald’s for me. I guess that was what she meant by “dinner.” I drove home alone. She hardly spoke to me in class after that, which was fine by me.
Any time I saw her flirting with a guy from that point on, I’d quietly warn them off.
28. Two’s Company, Five’s a Crowd
I once went on a date with a girl from OKCupid. It was latish (about 9 pm), and she sent me a message out of the blue. We talked for a while, and she wanted to meet up for food. I hadn’t had dinner yet, so I agreed. We were to meet up at a local diner. Her profile picture was reasonable. Not my typical type, but not awful. What showed up, however, was not great.
She was about 5′ 2″ and somewhere between 190-210 pounds. Rotund is the best word. That would have been fine if she didn’t also look like a toad. I’m trying to be nice here. Now, that too would have even been okay, but it wasn’t just her! She had brought her friend along (a 16-year-old). For some context, I was 22 and she was 20. To compound that, her friend had brought a toddler along, as well as another friend.
So here I am with three girls and a toddler that I don’t know. All three of the girls had brought energy drinks 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 one of the girls filled it with the energy drink. She then let the toddler play with the sugar container on our table.
She promptly spilled sugar all over the place and started licking it up. Meanwhile, the three girls were just laughing at the toddler and having a great time. They started talking amongst each other and not even attempting to include me in the conversation. After about five minutes of ignoring me, they started talking about guys from high school.
To make a 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 bill, and got the heck out of there.
29. Hitting Rock Bottom
About 10 minutes after picking a girl up for a date, she asked me to pull over to the side of the road for a minute. She then got out of the car and proceeded to take a poop on the sidewalk right in front of me.
30. Heartbreak Hotel
I was seeing this girl on and off. She told me that she had a hotel room for some cheerleading event she was coaching at the time and asked if I wanted to come over and keep her company. Her hotel was in King Of Prussia, Pennsylvania. I live in New Jersey. Offer of a fun, private hotel get together, but a bit of a drive? Sure, I’m in!
So I drive the couple hours out there to meet her, meet her in the hotel lobby, and go up to the room with her. To my surprise, her dad is in the room…because it turned out this was a cheerleading competition for her little sister. In other words, her entire family was there…
Her father got called unexpectedly into work (he was a firefighter), so he was leaving her the hotel room for the night. He was carrying his overnight bag out as I was carrying mine in. It was unbelievably obvious to him as to what was about to go down, making it extremely awkward for me.
I have never felt so uncomfortable in all my life.
31. Are You Gonna Finish That?
I went out on a date with a friend of a friend. He ate half my burger during dinner. What a great time that was!
32. Toad Be or Not Toad Be
I once tried using Tinder, despite my ugliness. I somehow matched with a girl who wasn’t too shabby looking. We texted for a few days until we were both free. When the time came for our date, I picked her up. She was very cute, and we went to dinner at a Japanese steakhouse. We had a good time, ordered a few drinks, and she eventually suggested that we go back to my place. Woo!
We stopped by her apartment to get her car and she wanted to grab some new clothes. She then followed me to my house and we made out in my driveway for a few minutes before starting to move towards the house. I was super excited. We got to my front porch and she suddenly screamed “Eew, what’s that??” before pointing to this cute little toad that used to hang out on my porch.
This was his second year hanging around my house and he had become almost like my pet. I explained all this to her and started telling her all about how cool he was and how I enjoyed knocking beetles off my porch light for him to eat and what not. Then, all of a sudden, this night turned into a horror movie. She walked over to him, looked at me, gave me some intense eye contact for a few seconds, and then proceeded to slowly stomp my toad to death.
Now, at this point, I was experiencing several emotions at once—shock, anger, rage. I shouted at her, “Why on earth did you do that??” to which she replied, “I wanted to make you mad so you’d be aggressive in bed.” I was speechless while I tried to process what I had just witnessed. I told her to get the heck off my property.
She flipped out and we started to yell at each other back and forth. After a while, I sprayed her with my hose and she finally left—only to show up again, topless, 20 minutes later on my backyard deck. She had walked back from down the road and pulled about six pickets down from my fence to get into my backyard.
The cops came. She cried her way out of trouble with them and finally left for good.
33. Good Things Come to Those Who Wait
I once went out with this guy who I met on a dating site. We were at a restaurant and he spoke very loudly the whole time. It was as if he didn’t have any volume control whatsoever. He was also very arrogant, so I didn’t even want to talk with him anymore after a few minutes. To top it all off, he looked nothing like his online pictures.
On the upside, though, the waiter we had ended up slipping his number to me. He could clearly tell it was a bad first date, and he took me on a much better date a few days later.
34. A Funny Thing Happened on the Way Back Home
I had a very disappointing date in high school. It was the dead of winter. Like -40 degrees. We had gone to a movie, and the whole thing was really awkward. She didn’t really seem to want to be there and was very detached. After the movie and the bus trip home, she admitted that the only reason she had even agreed to the date with me was because my friend had turned her down a few days earlier.
I wasn’t aware of that at the time. It was a pretty big letdown and the whole thing felt like a waste of time at that point. But I figured “Whatever, I’ll just head home and find something else to spend time on. I’ll get over it eventually.” I got off the bus and just wanted to get home as soon as possible. At the bus stop, there was a thigh-high railing around the front of the nearby parking lot. Instead of walking around it, I decided to step onto and then over it.
The second I stepped onto it, I realized it was coated in ice. I flipped through the air and lost everything in my pockets. I ripped my pants from the bottom all the way to the zipper. I then came down hard right onto the railing with my shin, fracturing it. It was still freezing cold out. I couldn’t just lay there until help arrived. So, I fished around in the snow, grabbed my stuff, and staggered home.
35. Sounds Like Someone Is Chicken
My worst date ever was when the girl I was supposed to meet never bothered to show up and I had to spend two hours sitting around at the bar by myself, drinking and eating chicken wings to pass the time. Getting stood up sucks!
36. Riding Off into the Sunset
My first-ever online date was with a girl who was into biking. I suggested that she pick me up and we ride to her favorite restaurant. She pulls up to my house, weighing 100 lbs more than her pics and wearing a skin-tight bright red Lance Armstrong bike suit with all the accessories. She then proceeds to almost get us killed while riding in traffic at least five times on the short two-mile trip.
She also sweated like mad through the suit. As if that wasn’t enough already, the restaurant she had chosen turned out to suck!
37. A Hair-Raising Story
I have long hair, which I absent-mindedly play with a lot. While on a date with a guy, he noticed that I had this habit and suggested that I try not to do it. The more I did it throughout the evening, the more angry he seemed to get about it. It got to the point where I did it again, and he physically grabbed my wrist quite forcefully before ordering me to stop touching my hair.
38. Plot Twist
In college, I once went out for a going-away party for a friend. There, I met some girl that a bunch of my friends knew. We got pretty drunk and had a lot of fun. Did shots. Danced. Did shots. Sang karaoke. Did shots. Chatted while smoking cigarettes on the patio. Did shots. Went back to the patio. Drank beers. Did more shots. Really liked each other.
So, we exchanged numbers before leaving and said we’d go out sometime next week. Now, 20 minutes after leaving, I literally passed out and landed on my face because I was so freakin’ trashed. So I was in prime condition this night. This girl knew I liked to party as only college kids can (which kind of horrifies me in hindsight—how did I survive?!).
So, next week comes and we line up a date. Since we still didn’t know each other super well, we decided we would go to that same bar where a bunch of our mutual friends would be. We sit with them on the patio and chat. She’s cute. But, that’s all she has going for her. Over the course of the evening, I find out that we are absolute polar opposites in every way imaginable.
Her dad is a preacher and she’s very religious. I’m not. She doesn’t like art. I do. She’s waiting for marriage. I’m not. She doesn’t like fishing. I do. She thinks hunting is cruel and that the outdoors are icky. I don’t. I’m also getting one-word answers to everything I ask. She keeps saying she doesn’t like anything I talk about, while she doesn’t even try to make conversation in return.
It’s so awkward that our mutual friends start bailing, shifting further and further away from us, until there are only three of us left in our section and everyone else is on the other side of the patio. After about 45 minutes, I decide that I’m going to need at least about eight more drinks to make it through this night. I ask if she wants another drink. She says yes and I go inside to the bar.
While I’m waiting to be served, I spontaneously say to myself, “Screw this!” I leave. I bail right out the back door. I don’t even care. I don’t say goodbye, I just leave and delete her number from my phone on the way out. I stagger over to a friend’s house, explain that I was just on the worst date ever, and proceed to get blackout drunk with him. It wasn’t until a week later that I learned what really happened.
Three days later, a mutual friend who we’ll call Kevin says, “Man, that date was pretty brutal! But it wasn’t right how she treated you.” “I know man, right?” “Yeah. I can’t believe you went to get her another drink, and she left before you got back! That was really rude!” Yes, that’s right. This date went so poorly that we both bailed without telling the other person—and neither one of us ever tried to contact the other one again, either.
39. Painting Quite the Picture
I once met a guy from a dating app. He knowingly used pictures that didn’t accurately reflect the way he looked and was shocked to find out that other people didn’t do the same. He kept saying “You look just like your pics!” in shock throughout the entire date. He then told me that I reminded him of his mother, as though he was happy about that…
40. Leaving Out a Key Detail
I met her in an adult soccer league. I asked her to grab breakfast that weekend, and she accepted. I picked her up, took her to a hole in the wall diner, and ordered the garden omelet. Throughout the entire meal, she talked about all the crazy stuff that she was into in the bedroom. I eventually got the check and then realized that my wallet was still in my gym bag from the night before.
I apologized, she paid for us both, and I went back to her place. She invited me in, and I couldn’t refuse as she had just bought me a meal. An hour later, after one of the wildest experiences of my life, we were lying in bed relaxing when she suddenly got a text and started to panic. “Oh my God, you have to leave now! My boyfriend got off work early and if he finds us he’ll kick me out!”
This was the first I’d heard of her having a boyfriend, and I suddenly realized that I had just slept with a woman on her boyfriend’s bed after she had bought me breakfast with money he had given her. Uh oh…So, I threw on half my clothes, jumped into my car, and knocked over their mailbox with my bumper in my rush to get the heck out of there.
When I got home, I discovered that my rear bumper now had a nice new crack in it. I guess I’ll always have something to remember that day by!
41. A Storied Romance
I once decided to try online dating. The guy I went out with had looked pretty cute in his picture. He showed up to my house when it was time for the date. He did NOT look anything like his picture. I later came to find out that the picture was him from five years earlier—and that he had gone through a BAD case of adult acne since then, which was still plaguing him.
We went to Long Beach and he said he wanted to go to Ruby’s or some other diner like that. As soon as we sat down and the waitress had handed us our menus, he informed me that he only had a little bit of money on him (something like $20). I inferred that this meant I had to order something cheap.
I ordered a basket of fries and a glass of water. He then proceeded to scarf down a bacon double cheeseburger, onion rings, and a strawberry malt—in addition to about 75% of the fries I ordered. I wish I was joking. Throughout the meal, he repeatedly lamented his last girlfriend, who had recently left him. He was practically in tears over the fact that she didn’t love him anymore, and he told me about how he wanted her back so badly.
I sat in stony silence the whole time. Clearly, I was just intended to be a sounding board to him. The date wasn’t really a date. It was a hostile kidnapping in which I was starved and had to listen to the ravings of an idiot.
42. Wearing Herself Out
My worst date was with a girl who spent the majority of our evening together shopping for clothes for another date that she had later that week. It’s kinda funny, seeing as how she was the one who asked me out in the first place.
43. The Right Way to Start the Millenium
It was the year 2000. I worked at a takeout restaurant, and a lady came in one night with a younger attractive blonde. After they left, the lady came back in and asked if I would be interested in taking the blonde out. I was told she was a German exchange student. I said sure and gave her my number. A few days later, the blonde called.
Her English was okay, but not to the point where it was super easy to communicate. We made plans to meet near where she was staying, and the older lady was going to drop her off. The plan was to go to a movie and then maybe grab something to eat after before she would call to get picked up when we were done. We met up and headed to the movies.
The car ride there was a bit awkward as she kept repeating herself, but I thought it was simply the language barrier and wrote it off. We got to the movie and she immediately excused herself to go to the bathroom. She came out and we finally took our seats after a long search for two spots next to each other. We wound up having to sit in the first row.
The whole time we were walking around, she kept grabbing onto my arm to seemingly balance herself. I still didn’t think much of it—but soon, the truth would come out. We sat down and, right away, she said she had to go to the bathroom again. I said okay, but she told me that she needed help. Here is where I started to worry. I walked her over to the bathroom and stood outside for what seemed like at least 20 minutes or so. This whole time, I had no idea what in the world was going on.
Finally, some lady came out and asked if I was waiting for someone. When I said yes, she told me that there was a blonde lady laying in one of the stalls. Just great! Not wanting to walk into the women’s bathroom, I went and got a manager who sent a female worker in and then closed the bathroom off. I finally went in to find her sprawled out on the ground with her shoes off.
Her purse had spilled out all over the floor, and she had clearly thrown up. The remnants were in her hair, and everywhere else too. The manager called a life squad after we couldn’t get her up. They showed up, along with the police. Fabulous! They, of course, grilled me and didn’t believe me when I had zero explanation as to what the heck was going on.
The squad took her to the emergency room, where I spent the next hour waiting for her to wake up after they pumped her full of fluid. Her blood alcohol concentration was extremely high from what I remember. When she finally came to, she told me she had been nervous about going on the date, so she had drunk some vodka. It must have been a massive amount.
She called the family she was staying with and arranged for them to come pick her up. Once I saw that she was okay and had people on the way, I got out of there as fast as I possibly could—never to see or hear from her again.
44. In the Driver’s Seat
A boy asked me out on a date and said he would plan it. I thought that was great! A man who takes initiative, what a change! He then calls me 45 minutes before we are expected to meet up, says his car isn’t working, and asks if I can come pick him up instead. I go over, and he invites me in. His apartment is a total pigsty, with comic books literally floor to ceiling like something off of a hoarders show.
He tells me that the place where he wants to eat dinner is a steakhouse over an hour away. I drive us, and he talks the entire way about his adult comic book collection. We eventually get to the place and sit down for our meal. He orders steak and lobster, while I order salad. At the end, the check comes, and he claims he lost his wallet.
I pay, but think to myself that he darn well didn’t lose his wallet because he would have at least checked his pockets before making the claim. I start driving him home. I’m staying completely silent because I now view this guy as a clown. Then, all of a sudden, I hear a sound. I look over and discover that he has pulled his pants down.
I immediately pull over, kick him out of the car, and leave him out on the side of the road 30 minutes from town. Screw you, Scott…
45. Start Your Engines
My worst date ever was when a guy took me to a Ferrari dealership just to lecture me on how Italian cars are awful and how he would never buy one.
46. If It Quacks Like a Duck…
I once went out with a guy on a simple park date. Got a snack—ya know, normal stuff. Then, out of nowhere, he pulled a gun out, shot a duck two feet away from us, and asked me if I wanted to take it home. Oh boy…
47. Selling Your Soul
I went on a coffee dаtе with a girl frоm Tіndеr. Halfway through, she pulled out a bunch of samples of some herbal tea product and started telling me all about why I should buy some from her. I essentially went to a sales pitch and paid for the coffee.
48. An Ice Cold Reception
Back in college, I was invited to an ice rink with a girl I liked and some of her friends. I did not know how to ice skate and I did not pick it up very quickly, but I wanted to try and impress her somehow. Well, I hugged the wall the whole time and made a fool of myself. The highlight was when I saw a flash of light as I fell in front of a group of people. Turns out I had fallen right at the moment someone had been taking a picture, so my failure was immortalized forever.
She took me back to my apartment and ended the relationship before it began. On a lighter note, the woman who is now my wife was also at the ice rink that night. We didn’t realize we were there at the same time until a year or two into our relationship when she exclaimed “Wait, you were that guy who couldn’t ice skate!! Yeah, she didn’t seem that into you…”
49. Take Me to Your Leader
I once went out with a girl who took me to a cult meeting after dinner. With her parents.
50. I Spy With My Little Eye
I was at work and a stunningly beautiful woman walked up to me and asked me out. I was in college and she was probably about 25 or 26 years old. It was an amazing date. She was funny and cool and insisted on paying for everything. At the end of our meal, she looked at me and said, “I promised myself I wasn’t going to sleep with you, but I’ve changed my mind.”
Back at her place, things got wild. But something felt off the entire time. She was very particular about positions and what parts of the room we stayed in. She also described everything we were doing in a very loud voice. By the time we were finished, I was creeped out. I knew something was up. On the drive home, I badgered her until she finally admitted that her fiancé had been secretly watching us the whole night.