The dating world is a terrifying place, and these awful stories don't make it any easier to navigate. Buckle up because finding true love will always be a battle.
1. A Crash Course In Romance
We met online and agreed to meet at a diner we both knew. I got there first. But the night took a horrifying turn the moment she arrived. Just after pulling in, she hit the gas instead of the brake, drove into the curb, then hit a light pole which fell over and landed on a parked van.
No one got hurt but she was pretty embarrassed. Never heard back from her.
2. Fine Dining
I matched with this guy on Tinder and he offered to take me out to dinner. I thought that sounded nice, so later that night he picked me up. We were driving and he asked me where I wanted to go. I told him I was fine with anything. BIG MISTAKE.
He said, "Okay then," and pulled into Subway. He then told me that he wasn't hungry, but that I should eat! So he stood outside of the Subway and watched while I went in and got myself food. At this point, I was already mentally done but I wanted to see how much worse it would get. Spoiler alert: it got so much worse.
So I'm sitting in the car with the stupid freaking sub on my lap, and he decided that it was a great idea to drive around, specifically through a dark, isolated ravine that was nearby. He drove for about 10 minutes into the ravine, parked the car next to an abandoned tennis court and said, "Okay, you can eat now”.
I was just thinking, "I really don't want to die here," so I choked down the soggy sub while he stared at me. The second I was done, he pulled the car out and drove me back home. I was so grateful to make it home in one piece that it took me several days to process how screwed up the entire date was.
But here’s the cherry on top: at 2 am that night, he came back to my house uninvited, carrying a bag full of stale donuts, and asked me if I wanted to sleep with him.
3. Not Up Her Alley
Last year I decided to text a cute girl that I had a class with the previous term to try to set up a date. She said sure, and we agreed to go bowling. When I got to the bowling alley, she was sitting on the railing outside the bowling alley waiting. I got out of the car and smiled at her. She said something that made me freeze. "Oh hey! I wasn't expecting to see you here!"
This floored me, but I couldn't think of a good response, so I acted like I wasn't expecting to see her either. I asked her if I should go inside and get a lane set up for us and she said, "Yeah sure, just hold on a bit...I asked another friend to meet me here”. When I asked who it was, she told me that it was her friend—that just so happened to have the same first name as me.
I went inside and paid for the alley and put on my shoes. I then put our three names in the machine. After waiting for 10 minutes or so, I got a text from her saying, "Where are you? I really don't want to be stuck here with this guy I used to have class with!" My instincts were right! She thought I was someone else.
She later came in and told me her friend—me—wasn’t going to make it. I asked her if she wanted to bowl anyway, and she said she didn’t like bowling.
4. No Means No
After a first date of dinner and a movie, he asked if I’d like to “have some fun” and took off his pants. I said “No”. He apologized for overstepping himself and I told him, “Hey, I totally understand and it’s okay!”
Now here’s the confusing part...he took my word “okay” as consent for “I totally want to do it now”. So he immediately took off his pants again. It was so awkward when I explained it was still a no.
5. I Blacked Out
About five or six years ago I met a girl that came into my work. I talked to her for a little bit and we seemed to really hit it off. She asked me if I wanted to go get dinner sometime. She said she'd come to pick me up and everything. That weekend we went out together to a restaurant on the other side of town. She was very interesting to me.
I really didn't tell her a lot about myself, because I kept asking her questions about what she was talking about. We'd just finished eating, I told her that I was going to get our meal since she drove us there. I had just given the waiter my debit card when disaster struck. I blacked out. This has happened two other times in my life, so it's not that common.
After my seizure was over, everyone in this restaurant was around me. People were holding my legs and arms. Everyone was scared, and someone had even called an ambulance. Usually, after a seizure, I’m in a bad mood. Everything seems different and it's kind of hard to explain. In this state of mind, I get up to my feet. I looked all over the restaurant for her, but I couldn’t see her.
I thought she maybe had gone to get help—but I was in for a rude surprise. Nope, she was totally gone. I made the EMS people wait for her as long as I could. I tried calling her. I didn't get out of the hospital until after midnight. I had to walk the whole way home by myself because we don't have public transportation in this town. I never heard from her again after that.
6. Just Can’t Catch A Break
Back in college, I met this girl and asked her if I could take her out to dinner. She said yes. I was ecstatic. Well, then I had to figure out where to take her to give her an idea of who I am and what I'm about. So I tried to do something that was thoughtful.
I've learned that there are two types of gifts: expensive and thoughtful. If you can't do expensive, which I couldn't, then you'd better go hard on the thoughtful. This was taking place in the southern US, but she was a freshman from Pennsylvania. I started thinking about things that be new and interesting to her. The answer came to me in a flash: Bojangles!
I would take her to Bojangles. It's cheap, it used to have fairly decent food, but most of all it's southern, and we'd be able to discuss regional differences in food and culture. Of course, it's also fast food. Really crappy fast food.
The evening of the date arrived. I drove her to the place and talked all about fried chicken and the South and tea and how it must be different from the North. We got there and ordered at the register, then moved down to pick up our tray of food. We waited. And waited.
I tried to make some small talk. You know, the small talk you make when something could interrupt your conversation at any moment...Then we waited some more. Finally, my dinner (fried chicken) was on the tray. The drinks were on the tray. Her sandwich was not.
So we stood there and stood there with the silence growing more and more awkward. Minutes rolled by that felt like ages. Finally, an employee noticed us standing there and said, "Did you need something?" I said yes, that we needed her sandwich.
The employee turned around and grabbed the sandwich from the place it had been sitting THE WHOLE TIME WE'D BEEN STANDING THERE and put it on the tray. It had been there since the beginning. Not a great start.
I picked up the tray and started walking back to a table with her. But there was an issue. Bojangles used to have the best sweet tea, so I always got a large. The cups they use for the larges are the kind that are smaller at the bottom, so they'll fit in your cup holder in your car.
That's great for a car, but NOT so great for balancing them on a tray. It fell over. Fortunately, it fell over onto the tray, but not before knocking her drink off of the tray onto the floor. She had gotten the smaller drink, which came in the waxed paper cup instead of the plastic cup that the larges are in.
That's important, because it means that when her cup hit the ground at about a 30-degree angle, the cup crushed and LAUNCHED the liquid inside out like a cannon. Onto her foot. Drenching her in Pepsi or Coke or some soft drink.
Being gentlemanly, I went and got her a new drink. I got back to the table and started trying to eat. I had ordered fried chicken, which I realized would mean that I had to eat with my fingers, which was stupid on a first date.
Not wanting to look dumb(er), I decided I'd try to avoid eating with my fingers by using the plastic cutlery provided by the store. This would have been a fine idea if not for the fact that Bojangles only provides you with a spork. Not a fork, not a spoon, not a blade. A plastic spork.
I'm trying to pry the chicken off the bone with this plastic spork and it's going nowhere. I can't get the chicken off the bone. I dug in a little deeper and really pulled, which bent the spork back a little, which served as a spring to launch my chicken across the table. I actually caught it before it could hit the floor.
I remember thinking to myself, "Well, just enjoy this chicken because this date is going NOWHERE”. I decided to just forget it and eat the dang chicken with my fingers. She was obviously not going to be going out with me anymore, so I decided not to worry about impressing her, just try to get out of the situation without looking any dumber than I already did.
I reached down and pulled off a nice piece of chicken with my fingers….and I missed my mouth. Seriously. I jammed the chicken onto my face. I don't know how I missed it, but I did. I just missed. Which of course smeared chicken grease all over my cheek. Oh, but it doesn't end there.
The girl was looking at me like she was waiting for me to tell her, "It's just a prank, bro!" I felt so dumb. We finished eating in silence. Finally, I said, "Well, let me take you back to your dorm”. I gathered up all the trash on the tray, walked over to the garbage can, and accidentally threw the whole thing into the trash. All of it, cups, the spork, napkins, THE TRAY. All of it.
I looked at the girl, she looked at me, and we both ran to the car. I've had some other bad dating experiences, but this one took the cake. I also remember being shocked when the car started when we were leaving. After the night I'd had, I was fully expecting to have to walk several miles back to campus in the dark.
7. From Zero To Tears In One Date
I went out with a guy who wore the puffy shirt from Seinfeld. I swear this was the same shirt. I looked beyond that, or at least tried to, and continued with the date. He later had a meltdown in his car because I said hello to a male friend we had seen while we were at a coffee shop and laughed when he told a story to me.
He said my laugh was very flirty. What he said next blew my mind. He said that he shouldn't have “fallen for me” so quickly and wouldn't have if he'd known I'd “cheat on him so fast”. By this point, he was crying really hard the whole way back to my house. It was the most awkward car ride home ever. We never talked again.
8. I Think I’ll Switch To The Salad
I went on a blind date with a woman who wouldn't stop picking at her scabs. She just sat there across from me picking away. I guess it was an unconscious thing. Then—to my horror—she made a pile out of them on the restaurant table. I excused myself to use the washroom and when I came back my soup was there, but the pile of scabs wasn't. No, I didn't eat the soup.
9. It’s Been A Slice
A few years ago I met a guy at a bar who was born on exactly the same day as me. That seemed like reason enough to accept his offer when he asked me out. He told me to dress up very nicely as we would be attending an art gallery opening. I got all dolled up and when he came to pick me up, he was in a t-shirt and jeans.
Okay, maybe I'd misunderstood the attire requirement. We got there, and it was in a warehouse out in the middle of nowhere. It was actually an art gallery, but barely. Some of his friends were there, but he wouldn't introduce me to them and proceeded to chat with them and ignore me the entire evening. Meanwhile, I'm dressed to the nines and they're also all in jeans.
After we left, he asked if he could take me out to dinner. I figured, whatever, at least I'd get a free meal out of this awful evening. I was so, so wrong. We hit up a nice pizza joint and ordered a pizza. As I reached for a second slice, he just looked at me and said, "Wow! A second slice? Really? Jeez, you're a house!" So I ate the rest of the pizza.
10. TMI
My worst date was my first-ever online date. We had been chatting on a dating website and agreed to meet at a cafe. I showed up about 15 minutes early. She calls me and says she is going to be a little late. I say “no big deal”. 25 minutes later, she calls me again and says she is going to be late as she locked herself out of her apartment.
I wait and wait. At this point, it's an hour after the agreed-upon time. I see a woman who matched her picture enter the cafe. Before I can go up to meet her, my phone rings. I picked it up, and she proceeds to shout at me, "Where the heck are you? Is this some sort of prank?" I tell her that I am at a table in the back of the cafe.
My first online date was informative, as I learned why some women only post pictures of their faces. She was extremely overweight. Furthermore, she was only in sweatpants and a sweatshirt. But all this is minor compared to what happens next.
After making some small talk, I ask her how her day was going. She asks if I really want to know. I mistakenly say yes. She launches into a rant about how she got fired from her last job because people were plotting against her, and a new job she signed up for was just a scam that stole her credit card information.
She also just got out of an abusive relationship, and her 25-year-old sister was abandoning the family to move to New York City. And on top of all that, she was just kicked out of school because people said she was plotting to kill someone, but she swears she wasn't. "People are always plotting to get me, it seems".
I was too frozen to leave at that moment and stayed for about another hour trying to make the most awkward small talk ever.
11. A Brutally Honest Red Flag
Working in bars and restaurants, I've been able to witness some absolute doozies. And boy does this one take the cake.
So, it's a fairly quiet night and it's pretty early, and I have a reservation for 6 pm for two people. A young guy shows up for that reservation about 10 minutes early. He tells me he's very nervous, as he's on a first date, and hasn't been on many of them, all that kind of jazz. It was kinda sweet, really.
Anyways, I seat him, and the girl arrives, like, 30 minutes late. She then proceeds to get extremely inebriated. About halfway through the meal, though, she answers her phone, takes the call, and starts talking about her date in front of her date, saying stuff like, "He's not really my type, I don't exactly like him but I figured I had nothing else planned tonight so why not".
The young man looks super discouraged, pays his bill, and leaves. Luckily, he didn’t let that date discourage him. He's a nice lad, I've seen him a few times at the bar I work at now.
12. It Wasn’t Love, Actually
This was a first date with a guy I met online. We'd had some nice conversations and decided to meet up one night for sushi. The night started off well enough, and I was really enjoying myself. About a half hour into the date, he starts getting a whole slew of texts and calls from who he claims was his dad. Being the slightly naive girl—it was four years ago—I shrugged it off.
So, the texts kept coming. He never bothered to put his phone on silent and checked every single text. He said his dad wanted to go work out with him. At that point, I had a good handle on what was going on. "Look," I told him. "If you aren't into me, that's fine. But have the guts to tell me instead of relying on your buddy to bail you out”. His answer left me stunned.
"Actually," he replied while standing, "it's a booty call. Thanks for dinner”. And he left. I sat there for a little bit, embarrassed because of all the sympathetic glances from the other patrons. The server brought the check over, but she leaned down to me and whispered, "I heard what happened. I took that jerk's order off so you only are paying for what you ate”.
That's when I started crying in the middle of the restaurant. I left the server a massive tip for her generosity and spent the rest of the night drowning my sorrows in Ben and Jerry's, and Love Actually.
13. Are You Afraid Of The Dark?
Before I got engaged, I was casually dating. I started chatting with this guy from high school—he was good looking and I figured I’d give it a shot with him. We were supposed to go out on a date, but I didn’t feel like getting all dressed up so I suggested he come over to my place and we could Netflix/chill.
He comes over and everything is cool until we sit in the living room to watch Netflix. I sit on my couch, and he does too. I had a corner lamp on in the room. He said, “We should turn off all the lights”. I’m like eh, the corner light is fine! I personally didn’t want to be in the pitch-black dark.
But then he gets up, creeps over to the corner light, stands with his back completely against my wall, and begins to flicker the light slowly on and off…Next to the corner is the doorway into the kitchen. He is literally not saying a word, just flickering the light off and on.
So I say, “You’re creeping me out, lol, please sit”. And he says, in between flickers, “Why...are....you... afraid... of... the... dark”. He then shuffles behind the doorway so I can only see HALF of his face and body. He has his arm reach around the doorway so he can still control the light.
He then begins giggling like a little kid and continues to flick the light on and off. Needless to say, no more dates after that.
14. Dine And Dash
We were both broke, so we went walking around this cute, teeny tiny country town near us, and then got McDonald's to eat in the car so we could chat some more. He almost immediately starts pressuring me to go sleep with him because he bought me a cheeseburger, so I owe him, he says.
He starts getting pushy, and I say, okay, but let's go purchase some protection from this gas station that's on the other side of town. I drove for this date, so I take us to the gas station and tell him to go get the stuff while I wait. I knew exactly what I had to do.
I wait for him to get in the door and go a bit farther into the store before I drive off, leaving him stranded in this tiny gas station in the days before cell phones got popular, in a tiny country town with no bus service, no ride shares, and everything shuts down by 6 pm.
I know from mutual friends he made it home, but they already knew why he'd been ditched at the gas station, so no one cared about his whining about it.
15. Three’s A Crowd
I met a girl online and she seemed reasonably attractive and fairly easy-going, so I figured, hey, why not? We met at a local coffee shop and chatted for a few minutes before a mutual acquaintance of ours happened to show up out of nowhere and began talking to the two of us. It turned out, they were both in AA together.
The two of them got to talking and I learned her long and sordid history of crazy stories involving booze. Then I heard the real reason for her wanting to date. I think her exact words were: "I'm trying to replace my boyfriend who passed this summer”. So, the guy decides to invite himself along for our date, neither of them asking me if it was cool for him to do so.
We end up driving to a bar—a fine thing for a couple of AA members to do—and the entire drive there they're playing the absolute most god-awful music on the radio I can think of. I'm in the back seat, this horrible music is blaring over the speakers while the two of them are chatting, and I'm thinking to myself: "Dear god, how can I find a way to get out of this?"
So we got to the bar and they proceeded to drink coffee and play air hockey while I tried to think of a way to leave. I ended up faking a cell phone call from my friend, saying I needed to go because she was in the hospital. The girl then proceeds to freak out at me for bailing on her during our date, at which point I just stared blankly at her for a second, blinked, and walked away.
16. Doggone It
Met a guy at a professional night out. He seemed interesting. He invited me out for Chinese food and a movie, but insisted I come by his house first to meet his four dogs, because not liking his dogs would be a deal-breaker. Cool, I love dogs.
I follow directions to his house, which is a mobile home with a small, fenced yard. So the dogs must be little, I think. NOPE. There were four large, mannerless dogs living inside this mobile home and the smell is completely encompassing.
Turns out "dinner and a movie" meant watching one of the thousands of VHS tapes and DVDs he owned while he tried to get the clothes off me, while four big dogs bounced around. I declined his kind offer of an incredible time in the bedroom and got out of there.
My clothes went directly into the washer and my car smelled like dog for days.
17. Bad Date Got Much Worse
Well, I was about 18 and working in New York City at my father’s printing shop. I had met this guy a few days before on a bus going upstate to visit my friend. I told my father I was leaving early to go hang out in the city with a friend and I was just gonna take the train home from there. I met up with the guy, and almost immediately he was weird.
Imagine that cartoon character Pepe Le Pew. Like he was trying to get all touchy-feely and huggy squeezy on the subway. Then he pulled out a disposable camera and asked if he could take my picture and tell people I'm his girlfriend. I, of course, said no, but I was a big people-pleaser and didn't want to hurt his feelings. So, I didn't end the date, but I couldn't wait to get away.
This behavior continued until we were walking down some random street and some scary-looking woman walked up to me and started getting in my face. That’s when I made a disturbing discovery. It was his girlfriend! I kid you not. We're in Midtown Manhattan, and we just happened to pass her by hanging out with friends. I tell her to get out of my face because I had no idea he had a girlfriend and am actually relieved she decided to show up.
I headed off down the street and he started to follow me and I just turned around and said, "Dude, you really don't want to do that. Trust me”. Since my train wasn't for a while I decided to go back to the office to wait. Well, the worst was yet to come.
When I got to the office I found my father cheating on my mother with the woman he hired to help with the filing: Bad date just got worse.
18. The Russians Are Coming
So my date came to pick me up at my place in his little sports car. Then we went flying down the freeway at a super high speed, which was a little scary I guess. We went to lunch, and he was so nervous that he couldn't eat. He insisted on facing the door, and kept glancing over there like he was waiting for someone to show up. Needless to say, lunch was a little awkward.
As he was zooming me back to my apartment, he started telling me this story about why he had to face the door. He was supposedly some kind of secret agent who was likely being followed by Russian spies. He dropped me off, and his parting words were: "If you are approached by two men with matching red ties and black suits, run”.
I never saw him again. I assume it was the Russians.
19. Didn’t See That One Coming
I was 19 or so, sitting at a bus stop bench waiting for the bus to go to work. This stunning woman sits next to me. Not long after, she starts talking to me. We have a pretty good conversation and I build up the courage to ask if she'd like to meet up sometime at a nearby coffee shop.
She says YES! We agree on a day and time then the last thing she says to me before I get on my bus is "It's a date”. I go to the coffee shop at the agreed time and see she is already there. But that's not all. She also has a male friend sitting right next to her.
No big deal, I figure he must be there in case I'm a creep or something. I sit across from her and we order a drink. Then right away she says, "So, what do you think about Jesus,” and pulls out a pamphlet. I reply, "I thought this was a date," and she says something along the lines of "I didn't think you'd show up if it wasn't”.
I ended up leaving right away before she saw me tear up. That was definitely my worst date ever.
20. The Secret Ingredient
I went on a blind date with a lady who wouldn't stop picking at her scabs. She just made a pile out of them on the restaurant table. I excused myself to use the washroom and when I came back my soup was there, but the pile of scabs wasn't. No, I didn't eat the soup.
21. Funnel Cake Reappears
The summer after graduating from high school I went on a date with a girl I had been friends with for a while. We decided to go to a fair a few towns over. We walked around, ate some fried foods, and went on a ride or two. Things were going great, and many laughs were had. We then went on a ride similar to a Zipper or Salt and Pepper Shaker.
There was lots of spinning upside down and so on. That’s when I knew something was about to go horribly wrong. The funnel cake I had earlier decided that it did not want to remain in my stomach. With her sitting next to me, I commence throwing up...and then we flip upside down...and my barf comes right back at my face. I had enough sense to keep most of it away from her, as she emerged from the ride puke-free. I, however, did not.
We have now been dating for over 6 years, are currently engaged, and will be married next summer.
22. You Had Me At Hi
This was, believe it or not, the only date I've ever been on. I met the girl online, and we planned to meet up at a museum. I got there and saw her a little ways away, so I waved. She looked my way, but then started walking away quickly. I then started walking towards her thinking she hadn't seen me, and was looking for me.
I caught up to her and said "hi", expecting a warm welcome. Well, I didn’t get one. She said she couldn't date me because I'm not her type. Now how did she get that just from the way I said “hi?"
23. I’ll Be Right Back
Things were going good, I mean real good. The city was celebrating its glorious hockey playoff victory. The local heroes were one win closer to winning the Stanley Cup. Women were, shall I say, juiced about the victory. Booze was fueling the celebration and breaking down inhibition barriers. That’s when I saw her and my night changed.
We made some small talk until the bar was closing. I was so happy when she said she was house-sitting nearby and wanted me to come over and hang out some more. So, we were at her friend’s place and kissing and hugging. She asks me if I have any protection. I’m not the kind of guy who expects this to happen, so I don’t. She tells me there is a store up the road and gives me her keys to go get some protection. That’s when I made the dumbest move possible.
I went to the store and uh…about 30 minutes later…where did she live again? And oh yeah: I’d left my phone there.
24. What’s My Name?
I went out with a guy from work who I didn't know much about. He turned out to be awful in many ways and was intoxicated when I showed up. The lowlight of the night was when he started heckling the small cover band that was playing in the bar.
The guy on the mic said, "I'll give you 10 dollars out of my own pocket if you can tell me this girl's name" and—you guessed it—he literally blanked on my name in front of a room full of people. But here’s the kicker: The next day he texted me saying, "You can try again,” as if I was the one who blew it.
25. The Babysitter
I'd been talking to this guy, and we finally decided to go on a date. He said he'd take me out for dinner and drinks. He offered to pick me up after work, so I said okay. He sent me a text saying "WE'RE" on the way. I immediately asked, “Who is we??”
Well, he's a single father, and his sister was supposed to be watching his four-year-old son, but something came up. Uh...Okay, I still went along with it. So he said he wanted to go home to shower first since he was in his work clothes.
We got to his house and he showered and fell asleep for like four hours while I hung out with his child who smacked me in the face TWICE. Luckily, after I told him not to do that anymore, we ended up getting along and having fun.
Turns out, he's a sweet kid. The guy finally woke up and we ordered pizza. I took an Uber home. I would have left before he woke up, but I didn't want to leave his kid alone.
26. Get My Good Side
I met someone online. I live in a mid-size city, and he lived in a small town about 40 minutes away. He asked if I would drive to him, which I wasn't wild about since there's not much to do in his little town and since we're both men and his town is very conservative, but I went with it.
He spent most of the date going on and on about conspiracy theories he believes in (all major politicians and celebrities are Illuminati satanists run by the Catholic church, etc). But the most unsettling part? He literally faced 45 degrees away from me the entire time, making sure I could only ever see him in profile.
Like, he sat sideways in his chair at dinner and always turned to the side while he was standing. At one point I stepped around into his field of view so we could look at each other, and he just immediately turned another 45 degrees.
27. I Ate It All
I had my first date ever in ninth grade all planned out with a girl I really liked. When I was running through the plan with my friends, they reminded me how socially awkward I was, and that if I couldn't carry the conversation throughout the date, there wouldn't be a second one. So, being the smooth guy that I am, I decided to prepare myself for the date.
I tried googling "how to talk to a girl" and "conversation starters" an hour or so before the date. The only thing was that I was too nervous to memorize the questions, so I decided to write them down on my palm for future reference. For the date, she’d wanted to go for sushi. Of course, I told her I love sushi to convince her I am a sophisticated and worldly gentleman.
The truth was, I'd never had sushi before and as I looked down at my plate, I realized why. I was such a beginner that I thought what I now know as wasabi was guacamole. If you don’t know, wasabi is a combination of horseradish, fire and hades. So, I ate the whole chunk of wasabi and there I was, practically sobbing and oozing mucus out of my nose.
I decided to distract her with a tactical conversation starter. The only problem was, my palms were too sweaty, and all the ink had bled. I didn't notice while I was wiping the wasabi-induced snot storm off my face, so now my face was covered in ink and snot. I looked at her and saw that she was staring blankly at me wondering what to do.
I happened to catch a glimpse of myself in the reflection of a window and I was in so much pain and so mortified that I just started crying. We ended up having to call my mom to pick us up early and drove home in silence except for the oldies station my mom had playing on the radio. We ended up being friends later on in high school and laugh about it now. To this day, she thinks I was only crying from the wasabi.
28. He Was A Naughty Boy
My good friend Vicki and her husband Will—who is a surgeon—are always trying to set me up: and I mean always. I usually turn down their offers, but they talked up this one guy named Ben. He seemed like a great guy: smart, a doctor, and his Teenage Mutant Ninja Turtle collection was bigger than mine! I really had no choice but to accept this blind date.
He took me to a pretty nice place for dinner, and I was kind of nervous, but nothing like super bad. Then he spilled his drink, and I’m pretty sure it was on purpose! I saw it! So, I was like What? I never, ever could have predicted what happened next. He started talking like a baby!!! "Ooopsie, I spwilled mwy dwink....I'm a bwad boyyy”. And I was like, "Ben? Are you ok?" I thought he was having some kind of a seizure.
But he kept at it. He continued with the baby talk, and then added something more: looking coy like a misbehaving child. Then he—I am not making this up—asked if "Mommy wanted to punish her bad boy". I was so out of there! I just got up from the table and walked out. He ran after—talking normally thankfully—and apologizing profusely.
I had to wait for my coat at coat check, so I was forced to listen to his apology. I assured him I wouldn't tell Vicky and Will about his kink. Then he went to hug me, and it lasted a little too long. I pushed him away and...well, there's no polite way of saying it…I felt something wet there, in his pants. I have no proof, but yeah, he did—against my leg. I just ran away and hoped I’d never see this guy again as long as I lived.
29. She Was A Heavy PETA
This was a second date with a girl that I actually really liked. We got along great, and liked the same music. So the date was beginning, and we went to dinner and to see a movie afterwards. It was really no big deal: all normal fun stuff. She lived about 20 minutes away in a somewhat rural area, so on the drive back, we're talking, and listening to some music.
I was starting to really, really like her, and then it happened. A baby deer jumped out in front of my full-sized SUV. The baby deer basically exploded, and messed my car up. I stopped, and the date was awkwardly quiet. She looks over at me, and I quote, "What is your problem?! Blah, blah, blah...I'm a PETA member”. Then she hit me right in the face. She stepped out of the car and ran the other direction.
I sat in the car for about 30 minutes trying to figure out what happened.
30. Let’s Never Speak Of This Again
I'm cringing even thinking about this date and it happened about 12 years ago...So we went for food and a few drinks, it was going great, and we were getting on really well. We started walking back to the train station and I felt my stomach cramp. I must have eaten something that didn't agree with me.
I try not to panic and tell myself I'll go to the toilet on the station platform. We get to the platform and the toilets are out of order, the cramps and spasms are getting quite bad now and I'm starting to sweat a little. I'm trying to keep up the conversation with my date but all I can think is that I need to not poop myself in front of them.
The train arrives and we both get on, I can't bring myself to go in the tiny train toilet when I know it's going to be baaaad, so I make excuses to my date and say that I have to head home instead. My stop was only a few in, so I quickly say goodbye and exit the train.
The cramps, sweats, and pain are horrendous by this point, so as I exit the train I pick up my speed and do a jog/shuffle across the platform. I trip over my own feet and land on the platform concrete. The impact of hitting the deck belly-flop style meant that everything I'd been holding in came out.
I mortifyingly looked up to see my date staring out of the train window, looking at me as the train passed. We never called each other, we both knew what went down at that station.
31. It All Came Crashing Down
This happened to a close friend. Her date brought her to the local rock-climbing gym which he frequents. She said she'd climbed before and seemed pretty fit.
She fell and broke her arm within a half hour of being there.
32. Licky Licky
I met this guy at a coffee place. He was nice and we met for coffee once more and then met for dinner at a bar. We were sitting at the bar, and I had turned to get the bartender’s attention. He leaned over—and did the unthinkable. He straight up licked my face, from chin to temple. I was visibly shook.
So he tried to playfully poke me to tone my "what the heck" face down and I asked him to stop. He then leaned in and whispered, "I'll just poke your sleeping body later"…I made him leave. I walked him to his car and had a bouncer stand by the door and wait for/watch me.
I received several messages a few days later. He was concerned he hadn't heard from me and was going to "stop by my parents later to see if I was ok”. I never took him to or spoke to him about my parents’ house/address. I told him I would call the authorities if I ever heard from him or saw him again.
Thankfully, I never heard from him again.
33. She Was At A Loss For Words
I met this girl on Yahoo probably about 10 years ago. We exchanged pics, and everything was looking good. We chatted online about various nonsense, and she suddenly asserted that she could beat anyone at Scrabble. I knew I was being baited for a date, so I challenged her to a game. Instead of playing online, she invited me over to her place. Well, I was in for an unpleasant surprise.
I get there and she looks nothing like her picture. Also, her "house" as she had called it is not a house. It is a trailer in a trailer park. She has no table on which to play Scrabble so we play on the floor. She has no drinks to offer me other than a bottle of Sam's Club bottled water. I obliterated her at Scrabble—twice. She then begged me to stay and sleep with her, which I did not.
34. She Could’ve Just Broken His Heart
I met this totally unbelievably hot woman and asked her out. She accepted and decided she wanted to go ice-skating. Awesome! I'd been ice-skating once, when I was six and I thought: how hard can it be after a gazillion years? So we skated. I didn't fall once, well, until after an hour and it was time to clear the ice. I fell just as I was getting off the ice and low and behold I hurt my wrist.
After skating, she wanted to grab dinner. I didn’t want to say no, but my wrist was throbbing in pain. I ate using one hand through the entire dinner. No problem, it was almost time to leave and my wrist is getting worse and worse. That’s when she suggested a movie. Um? Sure? Ok, make sure she sits away from my broken wrist since it's a horror flick and she might grab my arm.
So the date ended at around 1 am and my wrist was still screaming with pain. I stopped by a friend’s place for some painkillers and he said, "Wow, I think your arm is broken”. So next stop, the nearby Emergency Room! Yep, I had three fractures on my radius. The silver lining? One year later we were married and lived happily ever after.
35. He Was Majoring In Terror
I was in college and studying English. I’d just broken up with my high school boyfriend when a college guy—who was also an English major—asked me out for coffee and to study. We had been friends previously, so it wasn’t strange that we would hang out. While out for coffee, however, he started acting like it was a date. He bought my coffee and tried to hold my arm while escorting me around.
This also wasn’t a big surprise as he was an old-school gentleman who wore sweater vests and picked flowers for all the ladies. The part that made it a “fail date” was what happened when we sat down to drink, talk, and study. He slyly passed me a manuscript and told me he wrote it for me and had been too shy to give it to me while I had a boyfriend. He asked if I could edit it.
I obliged and before I could read it, he grabbed my hand and told me what a jerk he thought my ex was: and how I was better off without him. I recoiled, thanked him, and began to look at the manuscript. What I read made my blood run cold. The whole story was a revenge story about a boy who was in love with a girl. The girl in the story had a boyfriend who was a jerk. It sounded very familiar.
The story hero stalked the jerk boyfriend and eventually did him in. The murder scene was gruesome and incredibly detailed. He then, out of rage, also killed the story girl for not liking the hero boy all along. I don’t even remember my reaction. It was pure shock and terror. We did not talk after that. We eventually became friends again senior year, but I was always wary of him and didn’t like to be alone with him.
36. Signs From Above
We went for a walk, got a bit frisky rolling down a grassy hill, and just went at it right there behind a Mormon Church. First, a Mormon spotted us and told us we can’t do that there and just creepily watched us get dressed.
So we went elsewhere, at which point we both complained about not finishing. And the next spot we chose ended with about 30 mosquito bites on my behind, two on my junk, and she rolled over onto dog poop and cried that it was only on her.
"Go get a room," God said.
37. Money Matters
He took me to an Italian restaurant. After we ordered he got a phone call. He makes a small chitchat with the person on the other line. Then he says, “Mom, I know, I ordered the cheapest thing on the menu. Mom! I'm here with my girlfriend. I'll tell you how much the bill was afterward”. Two things wrong with that.
One, it was a first date, and I was NOT his girlfriend. Secondly, he lived with his mom (fine…I can deal with that) and his mom micromanaged all of his money—to the point of calling during dinner to see what kind of money he was spending. It was super creepy and really weird.
I saw him one more time to confirm he was a strange ranger and broke it off.
38. Running Him Ragged
I was the cause of a bad first date. I grossly underestimated how long it would take him (I’m a woman) to hike seven miles. I had to call a friend to get the ranger hotline to let them know we would still be on the trail after 9 pm when the gates closed.
By the last three miles, he was giving pep talks to his legs and threatening to eat the frogs that were hopping on the trail. I had to use my phone to light his way because it was super dark and he didn’t have his. Sorry, dude. You were a really nice guy. I didn’t mean to walk you to the point of collapse.
39. This Deal Was Not Sealed
It was five years since I’d graduated and I finally asked a girl I had a crush on way back in high school to come to stay with me in Toronto for a weekend. We both grew up in London, Ontario, which is a small town outside the city. She took the bus up and we hung out all day. I showed her the sights, took her out for a nice dinner, and eventually returned to my place to watch a movie she had brought with her.
It’s finally the end of the night and we're heading to bed: brushing our teeth and so on. We got into bed and started snuggling up. I figure at this point the deal was sealed, so I leaned in for a kiss and she flew back and yelled:” What are you doing!?" I was confused, so I asked her what she meant. She said something like, I thought you knew. I was still in the dark and said that I had no idea what she was talking about.
Finally, she blurts out: "I'm gay!" I still had to hang out with her all the next day...so awkward.
40. Poor Ricky
It was a high school date and the girl offered to pick me up because she had just gotten her drivers’ license and permission to use her parents' car. This was cool with me as I didn’t like driving. So, she picked me up and a little ways away from my place, a raccoon runs out and she obliterates it. I even felt the thing thump hard right under my feet.
So, my date's eyes go wide and she stares straight ahead silently for the next few blocks until we get to a stoplight. I decided to break the silence with a joke and said "Poooor Ricky!—a reference to the cartoon character. Her reaction was seriously unhinged. She completely freaked out. She was screaming, crying, and even punching me. Finally, she just kicked me out of the car and burned rubber down the street.
After about a block she crashed into a parked car. Being a good guy, I ran to make sure that she was not injured. She wasn't, but when she saw me, she started punching me again and screeching about how it's all my fault that she ran into a car. I just walked back home and watched some TV. She never spoke to me again.
41. Most Awkward Morning After Ever
When I had just turned 21, I was drinking at a bar and there was this cute older woman who was hitting on me and playing pool with me. We went back to her place that night, and we hooked up. In the morning, I was sitting on the sofa watching TV while she was using the bathroom. To my surprise, her son walked into the room.
To my further surprise: I actually knew him. We went to high school together and even played football once or twice. I never talked to her again.
42. Drink Up
I met a girl online and we started talking. Everything was grand. She and I texted often and seemed to be hitting it off well. So we meet and start having dinner. Everything is good except she just seems a bit off.
We order a pitcher of margaritas. We each have one and mid-sentence she just stops talking and stares at her hands. Just...looking at them. I ask if she's ok and she says, “Oh, I'm sorry, I'm just really tipsy”. I say “Really? We've only had one drink”.
She says then, “Oh, I've been drinking all day”. Now, I stop and think about past conversations. She texted me a lot saying, "Hey I'm a little tipsy walking home, keep me company”. I start thinking this might be a trend with her. She then proceeds to faceplant into the table. I think she's joking because it was so exaggerated.
I laugh and realize she isn't moving. I tap her and wake her and I call for the check, which was a looooot more than I'd figured. She then asks if I could walk her home. I said I would as she was in pretty rough shape. We start walking more and more and then I ask how much farther. She says another mile.
So we walk some more and finally get to her place. She offers me some water and then asks if I want to stay. I politely declined and she angrily kicked me out. So, that was that. I had to use a GPS to find my way back to my car.
43. Drama King
This is technically a breakup, but it happened on a date. I tried to break up with him in private in the car. He said he needed a pause on the conversation, took us into a restaurant, then proceeded to burst into tears in front of everyone.
The best bit is that a few weeks later, he came into my work pretending that we hadn’t broken up and I had to break up with him again...while he cried...in front of his sister who was my co-worker...
44. Telling Tall Tales
I got the friend call bail-out one time. The girl had to go to the bathroom right in the middle of the date so I knew it was coming. She kept talking once she got back for a few minutes. Her story was rather impressive, though.
She didn't stick me with the “my friend needs help” act. She told me that a bus crashed, and she had to get back to the hospital because there were multiple deceased kids. That was interesting.
45. He Got Set Up
I was working at Gamestop—which I took way too much pride in at the time—and this cute blond came in and was looking at the used DVDs. She was trying to decide between season one of Buffy the Vampire Slayer or season one of Angel. Being a huge Joss Whedon fan, I offered my opinion on the matter, and we flirted a bit. I finally got the nerve to ask for her number, and surprise, she gave it to me. I called her the next day and made plans for dinner.
On the day of the date I woke up and couldn't stop throwing up. It turned out I had a stomach bug that was going around, but I decided to tough it out. So, I picked her up and asked her where she wanted to go. She points out a place across the street. It is the dirtiest, most disgusting hole-in-the-wall Mexican place I've ever seen.
I tried to be cool about it, so I didn't say anything and just went with the flow. I ordered my food, and she ordered the most giant burrito I have ever seen. I could hardly sit up straight because I was so sick, and this girl started to devour this burrito like she had never eaten before. Cheese and beans were dripping down her face, and sour cream was falling on the table. It took all of my might not to vomit.
Just as I was about to call it quits, this older woman—about mid-50s—and a younger man in his 20s came up and started talking to my date. I still can’t believe what happened next. She eventually introduced them as—get this—her mom and step-dad. I introduced myself while trying my hardest not to show my absolutely shocked face because of the obvious age difference. To my horror, they decided to join us for dinner.
Trying to be boyfriend material I agreed, and my date switched sides of the booth and practically sat on my lap. I spent the next 20 minutes listening to her mom talk about how they had to move out of their house because a ghost was haunting them. I put down 20 bucks to cover my and my date’s food, and went to the restroom to get away from the crazy.
When I came back, I was in for an infuriating surprise. I looked at the table and realized that the 20 dollar bill was missing, Sadly the restaurant bill was still there unpaid. I looked around for my money but found it nowhere. I could have sworn I paid the bill, but I wasn't about to accuse them of taking it, especially since I wasn't 100% sure I’d put it there. I should have checked my wallet, but I didn't want to flash cash around the restaurant.
So, I put $20 down again, and made sure I handed it to the waiter on his next pass. Being that I was lost in my head ignoring the mother, it was likely I’d imagined putting the money there. Finally the nightmare was over, right? Not quite. We were just about to leave and the mom asked the husband for his wallet to pay the bill for their huge meal. He delicately explained to her that he was without said wallet, and she replied that she hadn't brought her purse.
That’s when it happened. Both the old mom and the young stepfather both slowly looked up at me, and—much to my disbelief—asked me to pay for their food. I don't know why I said yes. Maybe it was because her daughter was hot, or because she was rubbing my thigh after knowing her for like 25 minutes, but I paid it. Forty more dollars!
So I finally took her home, and she begged me to hang out longer, but at this point, I just needed to get away. I waved and smiled from the car, and sped out of the dirty town she lived in. So, here is the real kicker. Before the date I went to the ATM and took out exactly $200 in twenties. I decided to look in my wallet in the car, knowing there should be 60 dollars missing, $40 for the parents, and $20 for my date.
There was only $120 remaining in my wallet. I screamed at the top of my lungs "I did put down the $20 and someone at the table had taken it”. I was mad for quite some time, but after I told the story to a few friends I realized it was pretty funny. I actually ran into the crazy woman years later at a party, and the craziness continued.
46. She Built Him Up
I had a huge crush on this guy that worked at my local ice cream parlor. I only knew him from ordering my favorite ice cream flavor and blushing like crazy. Somehow I got the courage to ask him out, and he agreed to meet up at a bar near his house. I made it sound really casual. Like, "Oh, I'm just in the area!" The truth was I had planned it for weeks—months even.
He said he was just staying in to catch up on some reading, but he'd meet me anyway. I was so nervous that I was shaking and downing Budweisers to take the edge off before he showed up. While heading to the bar, I ran through a thousand different scenarios: what it would be like to finally talk to him and show him I wasn't a total idiot or awkward.
It didn't help that on the way into the city it poured for the like five minutes. I was actually out on the streets, so my clothes were drenched, my make-up was a wreck and my hair was a frizzy afro. But I didn't care, I had to see him. When I got to the bar and entered I just stared at him in shock. He’d brought along his girlfriend.
47. Hit And Ruin
It was my first year of community college and I met a girl on an online dating site. Well, she looked a little different from her picture but meh—she was mildly cute and we were both kind of excited to get going on the date. Fast forward after a movie and deep conversation over an upscale Chinese joint—it was time to drop her off. Things were going really well: a second date was imminent.
We spoke for a bit in the car. It was almost one of those "we don't want the night to end" moments. Eventually, we started fooling around. Keep in mind, we were in the car and were located in a somewhat distant part of a mall parking lot. Suddenly a security guard's jeep lights flick on. It was night and you could easily see it from across the parking lot.
So, I do the only logical thing and flip it into first and take off. Unfortunately for me, the windows had fogged quite a bit. It was a total disaster. I realized far too late that I was about to smash into a concrete barrier with, ironically enough, a stop sign attached to it. She called her parents to come to give her a ride and that was their first impression of me. They didn't want her speaking to me anymore.
48. Good Enough
My first date was my worst date. After an excruciatingly long car ride listening to him discuss his love of clubs and bottle service, we get to the restaurant he refers to as "enough of a hole-in-the-wall for a girl like me”. After ordering he says he needs to check his bank account, followed by him telling me to cover dinner (I'm fine with paying, just maybe ask politely).
Then he, and only him, spoke for the rest of the dinner, explaining how the earth is flat and he is going to be a senator on Mars in 10 years, so any woman who seriously dates him will need to be supportive. Afterward, since he drove, he dragged me to a club.
Upon him uttering, "This is going so well!" I explained to him that it, in fact, was not, given that I had yet to even have the chance to speak. He then asked him to list examples. After saying this was the worst date I ever experienced, he sat down next to me and asked, "So we can be friends who possibly become more?"
I promptly called an Uber. He texted me asking me on a date every day for a week straight until I finally blocked the number.
49. Shortchanged By The Universe
I arrived early at the coffee shop because I was nervous. When I parked, I realized I forgot my wallet at home. Mind you, the coffee shop was 30 minutes from home, and we were supposed to meet in 10 minutes.
So I scrounged around in my car for loose change. Found $2 in quarters, nickels, and dimes. I hurried in and bought the cheapest coffee I could. She comes in, confused that I already got something, and orders her own—very gentlemanly of me not to offer to pay with the rest of the nickels and pennies in my car, right?
We sit outside, with the setting sun in my eyes, but I'm too proud to move so the sun is blinding me the entire hour we are there. Honestly, the conversation was pleasant, but at the end, I shifted my weight on this wooden chair I was sitting on…and heard a loud CRACK.
Sure enough, the chair was broken. I know I’m a large dude, but this just had to happen now? I wasn’t surprised when I didn't get a call back from that date.
50. Well, That One Backfired
I haven't had many dates but the worst—and funniest—was from Tinder. The plan was to start at my house as a double date then, and if it went well, we'd split up and go out.
It never got to the last part because he took a dump in my toilet, blocked it with toilet roll, got embarrassed when my friend went in, and left. Oh, and he forgot his jacket in the rush so got one of his friends to come and get it the next day.
51. The Cat Had Their Tongues
I went out with a boy from a previous job once. It was when I was incredibly shy, and I'd never been on a "real" date at 18. I didn't know how to behave. I'd thought he was extremely outgoing and talkative, but I guess he just played off my behavior and was twice as awkward. I think we said about five sentences to each other the whole night. We never spoke again.
52. They Met Half Way
This happened to me before cell phone use was widespread. I was in college and there was this gorgeous girl showing some interest in me. Let's call her Sheila. The thing was, I had a girlfriend and most of the time I was with her when I saw Sheila on campus. So, we just said “hi” and small-talked a bit, which drove my girlfriend crazy with jealousy. I didn't want to dump my girlfriend, however, based on a purely physical attraction.
Near the end of the year, my girlfriend and I broke up. I didn't see Sheila anymore, and I assumed she had probably finished her courses. The following year, I'm studying in another city, so I called a common friend, let's call him Denny, and asked him for Sheila's number. After a couple of tries—this was her parents' home number—I had her on the phone. She said, "Yes, Denny said you were going to call. I don't know who you are, but we can meet halfway at the train station”.
So I took the train, very anxious, feeling a bit creepy, but well…this was my only chance to see her again. I didn't see her at the station so I waited. The crowd slowly scattered away, and I noticed a girl waiting at the other end of the station. I didn't know her and was getting a bad feeling. After a while, she came and asked if I was there to meet her.
It turned out that Denny knew another Sheila and thought I was asking for her number. The worst thing is she knew me by sight, but I had no memory of seeing her before. I had to decide quickly whether to go on with the awkward date or tell her the truth. Being a mostly good guy, I told the truth. She was really nice about it, and we laughed together. Then we went for a walk and talked for a while. She knew the other Sheila and said I should call her.
The following day I called Denny again asking for the other Sheila's number. He didn't have it, so I never saw her again. A few years later, some internet searching revealed the Sheila I didn't meet had become a famous DJ.
53. Snap, Crackle, Gone
I had a few awesome dates with a guy I met online at Geek2Geek and decided it was safe to tell him where I lived. I invited him over and we were enjoying the start of what was supposed to be an evening of movie-watching and talking when he suddenly bolted up from his seat. He then started walking around my apartment, snapping his fingers and oddly shuffling his feet around and swaying a bit.
He continued with this crazy person dance for about half an hour. Of course, I was wondering what was going on when he ran over to me, gave me a quick peck, and said he had to go. I asked him to stay a bit longer, but he refused. I was pretty disappointed. I kept asking myself if I had done something wrong, Things seemed to be going well.
We did continue to go out again, but it wasn't until a year later that he filled me in on what was really going on that night. Apparently, he had something inside him he really had to get rid of. The urge to rid his bowels of the demons within had hit him in a major way mid-evening. He’d started to become a bit flatulent, and he was trying his darndest to cover his emissions with the snapping and swaying around.
When he couldn't take it anymore, he flew at the speed of light to a Denny's about a mile down the road and used the bathroom. He was too shy to desecrate the toilet in my small one-bedroom apartment, and I don't blame him. Five years later, we still laugh about it, oftentimes snapping and dancing around the room like idiots, desecrating the toilets in our apartment with bold, unabashed fervor.
54. Dr. Yuck
I ask what he does, and he says, "I don't like to brag about my job, you know the fact that I save lives every day”. He was a doctor, and he said that with no sarcasm. Then he gets angry because he asked me out on a dating app five years before our date and I didn't respond to his message immediately.
I tell him it was an old account I never logged into he says, "Goes to show girls are so fickle…” And the icing on the cake? He admits he actually has strep throat and "I actually shouldn't be on a date right now”. Gross.
55. Third Time’s The Charm
In my sophomore year of high school, I wanted to go see a movie with my date. At the first theater, they asked for ID for the first time ever. I wasn’t 18 and couldn't get tickets. At the second theater, the movie was canceled after the AC broke and the heater reached 95 degrees.
The third theater didn't have seats next to each other. She still wanted to watch it, so we sat in DIFFERENT ROWS. Unsurprisingly, there was no second date.
56. A String Of Bad Luck
There's honestly no way for me to say which date is worse. I've had many bad dates, but these really take the cake. I went on a date with someone that seemed normal until she revealed that she was convinced we were all part of the matrix.
Another person I dated was a biter. I had to go to work and see my family with scars and bruises on my neck because she bit and yanked. I thought I was gonna die. And one date abandoned me at a club because I was out of my introverted comfort zone.
I walked home, then ended up peeing my pants because I was wasted and didn't really care as I was going through a depressive episode. So, as you can see, my dating life has never been easy.
57. Miserable In Missouri
I went on a date with a girl that I’d met online. She seemed cute, funny, and all that. About 30 minutes into our conversation at the bar, we realized something awful. It seemed that we had gone to the same family reunions as kids. After talking about it further, we realized that we were actually fifth cousins or something like that. Man, I hate living in Missouri.
58. Kentucky Fried Christian
Way back in the day, I met a dude on Myspace. We chatted online for a while and decided to meet up for our first date. To my horror, he took me to a fast food place: KFC to be exact. If this wasn’t bad enough, while there, we met several of his male friends. The guy was an average-looking dude, nothing to write home about, and kind of short. However, one of his friends was a hottie and was giving me eyeballs.
I was trying to be nice and not notice this and gave my full attention to the date. All his friends were woo-hooing and congratulating him on "getting' a girl" This made me assume this was out of the norm. In spite of everything, things were going okay until he started asking me lots of questions about church and what my religious beliefs were. Being pretty Agnostic, I kind of just gave him vague answers, and tried to change the subject.
After our lousy fried chicken date with his bros, he took me home. In the parking lot, he reached under the seat of his truck and pulled out a copy of The Purpose Driven Life. He said, "I really like you a lot, but I don't like that you're not a Christian, so I got you this”. I'm already out the door and ready to call this a night, when he whips around the side of the truck and pushes the book into my hands.
Then he proceeds to attempt a sloppy kiss attack, which I escaped with quickness. I said goodnight and went inside. He texted me several times that night, to which I responded with: “I don't think we have much in common”, and told him there would not be a second date. He did not like this very much and proceeded to text me on the dot, like a stupid cuckoo clock every 15 minutes for the next few weeks.
59. She Took It Out On The Door
I'm not the best at “getting the girl”, but I think I know why. I'm a 19-year-old community college student who works at a video game store, has no car, and still lives with his mom. Anyway, I tend to not really worry about it because I used to try hard to impress girls and it just got to the point where I mentally said “forget it” and just moved on.
My attitude is: “if someone comes along and it happens, it happens”. Now, my best friend since the third grade told me a friend of his saw my Facebook pictures and thought I was cute. He proceeded to text me a picture of her and told me that I should meet up with her. Well, why not, right? So he gave me her number, I called her and we set up a date on a Friday at a pizza place.
We went on the date and everything seemed completely normal. We had a lot in common, and I thought something might come of this, but oh dear god how wrong I was. We finished dinner, and I took her home and said goodnight. She then proceeded to drop off all contact with me for no good reason. I wasn't completely heartbroken or anything. More like, "Whatever, another one down”.
After four more months of no contact at all, I was chilling at home, just getting ready for work and the doorbell rang. Through the peephole, I saw a familiar face: it was her. I immediately started thinking “how in the world did she find out where I live?" I didn't answer the door due to being half-dressed and just getting out of the shower.
The girl then proceeded to go ape crazy on my door. Like, pounding, screaming, punching, kicking and I swear once she might have even head-butted the thing. I think this because my door was metal and there were dents everywhere, including one that was about where her head would be. I didn’t let her in and she eventually left. Good riddance.
A few days later, she called my workplace and asked for me. Once again, I have no idea how she knew where I worked. On the phone, she tried to rope me into some rant about why she broke off contact and that she was sorry for almost bashing my door down. I knew this would go on for hours, so I made some excuse about the store being busy and hung up without waiting for a response.
I don't know what I did to make her secretly want to kill me, but it gets worse. She called me at about 10 pm the same day and asked me to meet her in the park. Now, this park had barely any lights, was nowhere near any kind of houses and the authorities barely ever went there. It's called the “dealer’s grounds” because literally all of them are there, selling their wares. I should have just said no, but curiosity had piqued me.
So I meet her by the swings—because swings are still awesome, despite me being 19—and she calmly explains that she dropped contact with me because she went to a mental hospital for months. Again, this is where I should have picked up and ran, but I was slightly interested in the rest of the story. Mostly I wanted to know why she thought she needed to beat my front door down. Doors aren't cheap, after all.
Anyway, she says she found my name in the phone book and called our house, but the line was disconnected, so she just went to the address she found after a lot of Googling. When I didn't answer, she told me she thought I hated her for not talking to me for months and wasn't trying to break the door down, but rather she was punishing herself for being an idiot: her exact words.
I was silent for a little, then said everything was fine and not to worry about it, but I don't really want a relationship at the moment. I mean, who would after that? She then throws herself on me like a rabid zombie, and tries to kiss me. I push her away and get off the ground and start walking, very fast, away from her.
She then tackles me, and I mean really tackles me, to the ground and she pulls something out of her coat pocket. It was a syringe. Full of what, I have no clue. I wasn't gonna stick around to find out, so this is the one time I hit a girl in my entire life. I shoved her off me yet again. I then booked it back to my house.
I never saw her again. I'm guessing she gave up.
60. Is That My Ride?
I once was asked out by the mate of some friends. He asked for my number and called to ask me to dinner. He asks if I mind if he picks me up in his work vehicle. I have been in the corporate world for a while so I'm thinking it’s a company car, zero drama. Looking back on it, I realize I should have asked what he did for a living.
The night arrives, he turns up...in a garbage truck. But wait, it gets better. I decide “Ah well, he did ask and I said yes”, so we go out for dinner. I can only assume he was insanely nervous because he proceeds to get inebriated—to the point that he asks me if I can drive the garbage truck home.
Now, this thing has four gear sticks. I can only drive an automatic. So this numpty drove me home, in a garbage truck. Then asks if he can stay the night.
There was no second date...
61. Playing With Fire
My first date was definitely my worst date. The girl started lighting matches, would put them out with her fingers, then eat the burnt matchstick head.
62. Just Watch Me
My worst date was at boarding school, on a college campus. We were both straight-edge dweebs, so we went to a party at the student center together. He got bored in about 15 minutes, so we snuck off into the building together. I thought it was gonna be for some, like, making out and stuff? No.
He found a computer lab and made me watch him play League of Legends for two hours while he tried to explain the game to me. If you meet a hot guy and he's single there is probably a reason.
63. Left On The Bleachers
I was in 10th grade and this guy I really liked invited me to a soccer game. This was only about the second time we ever met. He ended up seeing his ex-girlfriend there and talked to her nearly the whole time. I sat in the bleachers alone trying to call my parents to come to pick me up, until some random guy from the marching band came over and played me a "song" on his trombone to make me feel better. I think he'd been playing trombone for maybe two months at the time so it wasn’t very good.
Wikimedia Commons, Derek Bridges
64. She Didn’t Even Like Calvin
First off, I should mention I've never been on a successful blind date. I think my friends purposely try to torment me by finding these girls. Here’s the one I remember as the worst. She was a vegan, although no one mentioned that to me. I guess she didn't think it was important to mention that to me when I told her I'd cook us dinner and asked if she was picky. So, I spent a good hour making an amazing Italian dinner: none of which she'd eat.
So we went to a vegan restaurant, and I ended up eating what equated to grass, while she told me about how our "meat culture would be the end of us all.'' We then went to see a movie. Midway through the movie she told me: "let's go, cause I want to show you something". I'm thinking: okay finally things are starting to pick up a little. We go back to my place and she runs up the stairs to my room.
I told her I'd be up in a moment and ran to the bathroom to do a quick prep for some very intimate playtime. I walked into my room with my shirt off and a grin on my face. She was sitting at my computer and had a website open. I ventured over to see what it was. It was about women's liberation and how horrible women are depicted in modern movies. Not at all what I was expecting.
For the next 10 minutes, I’m nodding my head pretending to understand what was coming out of her mouth in hopes that I might still get laid. She was really cute after all. After she thought she’d convinced me of whatever she was saying, she saw my old Calvin and Hobbes poster and said, "I never liked that comic". That was the last straw and I asked her politely to leave.
65. He Was Too Prepared
This was the first date I had with a woman I met online. She was attractive, and I was really excited. As I'm driving her back to her car, the glove box of my car suddenly pops open and a box of Trojans falls in her lap. She was clearly not impressed. No, I’m not a player. Here is the reason why my glove box was full of prophylactics.
My buddies were so excited that I actually had a date—it didn’t happen that often. So as a joke, they’d given me the box of Trojans. Like an idiot, I had thrown them in the glove box of the car. I wasn't planning on getting any on the first date, but I forgot I had them in the glove box when I went on the date. Honest!
66. It Was Like Watching A Car Crash
Online, her profile picture was cute. We had about four or five normal conversations before we decided to go to the movies. Now, I hate taking dates to the movies because this minimizes conversations and getting to know somebody in person, but I was like, “She’s cute, what’s the worst that can happen?"
Now, let the record show she chose the time of the movie and what time I was picking her up, so it's not like she had no idea that she had to use the bathroom. The movie theater was about 15 mins from her house. As soon as she got in my car, she seemed intoxicated, threatened to kick-fight me if I tried anything funny. This all happened within the course of 10 minutes.
On the tenth minute she said "pull over," so I did. I couldn't believe what she did next. She got out of my car on a sort of busy highway street and proceeded to take a dump within eyeshot…it was one of those times where it's hard to look away. When my brain registered what was going on I leaned over, closed the passenger door, and drove away.
67. The Double Date Disaster
So for starters, this was my first date. First date ever. I had no frame of reference for this, but I had just turned 16 and the guy had been cute at school, so the bar was really low. He somehow managed to limbo himself under it.
I didn’t want to go on a date without another couple because I have no trust in people. He had a big friend group and I knew all of them, so he assured me this wouldn’t be a problem. When I got to his house, the person he’d asked to double with us was...his aunt, who he apparently lived with.
She was 21, I was 16, already great. Her date showed up and he was not aware it was a date. He thought they were just hanging out, not chaperoning her awkward little nephew and his new love interest. He was Polynesian. She made Hawaiian haystacks.
He’d never seen those before, but he walked into the house to the scent of badly burned rice because she couldn’t cook. He saved the rice, everything else was straight out of a can, it was great. They hadn’t planned anything, so they decided to throw blades with us in the backyard.
I did better than my date, he was upset, then his aunt nailed him in the behind with an airsoft BB and he was REALLY upset. To salvage things, his aunt suggested we go bowling. I was wearing ballet flats, so I had to wear his weird too-big 2010 teenage nerd socks, which I already had too many questions about that I didn’t want answered.
So we headed out to go bowling, but not before he tried to reclaim his teenage masculinity by squashing a spider on the wall... by kicking it, and kicking his leg right through the wall along with it. His leg got stuck. His aunt had to help him. I was not impressed.
Finally, we get to the bowling alley and walk in and we’re all really good…but then it gets really awkward because the manager is his aunt’s recent ex. So eventually the date ends, and he tries to kiss me in the back seat of his aunt’s car with both the aunt and her date watching. She cheered.
I’d like to say that I didn’t go on another date with him, but this wasn’t even the worst date I had in high school.
68. Taste Test
He stuck his fingers in my dessert, licked his fingers, and did it again!! I ordered a lemon meringue pie and offered for him to try some. He said “no” only to then proceed to say, “Actually, that looks good". Then he sticks his fingers in for a taste. Yuck!
69. Do You Hear Wedding Bells?
I met this girl on a dating site. We exchanged pictures, talked for a week or so and set up a date. When I showed up at the bookstore for our date, I’m facing someone who does not look at all like her picture. She was way taller than I thought—and built like a football player. She was also very masculine and covered in tattoos. I'm a nice guy, so I follow through with the date.
She wasn't crazy from what I could tell at the time. I walked her to her car and tried to hide my terror of what I saw in her back seat: a wedding dress. The hairs on my neck stood up and my Spidey-sense was deafening. So I asked, "what's the wedding dress for?" She said, "well...I thought if the date went well”… I waited for what seemed like forever for her to smile, laugh or anything that would tell me she was joking, but nope. I said nice to meet you and speed-walked myself to my car.
70. There Was Dirty Laundry Everywhere
So, I had recently dumped my girlfriend, and she was coming over to take some of her stuff out of my apartment. The thing was, this was really bad timing. At the same time, I was supposed to be meeting this really cute server at her job to pick her up after work and take her out. So, I foolishly left my ex at my apartment and went on my date. This was a big mistake.
So, I show up at the pizza place where my date worked, and she tells me to hang out for a few minutes while she clocks out and all that, and I sit down at a table. At that moment, my ex walks in, and sits down across from me! She had followed me! So, I see the other girl come out from clocking out, give me a funny look, and she just sits down at the table next to ours.
At this point, my ex is grabbing my hands and literally begging me to give her a second chance. I was trying really hard to be nice, but firm. She started crying, and my date finally got up and walked away. I don't know what she must have thought hearing my ex spill all our dirty laundry right in front of her. My ex didn't have any idea what was going on, and never gave my date a second look.
Needless to say there was no second date.
71. Honest Was The Best Policy
I went on a date with a girl in college who I really wanted to sleep with. Turns out my attraction was only physical, and I couldn't even make it through dinner without wanting to kill myself out of sheer boredom. I finally just decided to be honest and said: "I'm sorry, I don't want to waste your time or mine. This isn't going anywhere" I then got up and left to go meet my friends at the bar.
72. A Night To Remember
Back in the day, I was on extended leave and was going through some rough times. So I went to Colombia to learn Spanish. I was out with some guys from the Spanish school and spotted this absolutely stunning woman. I knew I had to ask her out, even though my Spanish was still pretty basic.
So, I went ahead, asked her out, and to my surprise she said yes. One day later, the day of the date, I didn't feel so well but I decided to go ahead, I was so excited. So I went there, picked her up and we went to a nice restaurant. Afterward, we went for a walk on the beach—yep, sounds cheesy but it's true.
Right then, I started to feel really bad, becoming dizzy and all. That’s when it happened. I had to throw up—not normally, but with all the power my body could give. I don't remember lots about it, apparently, I fell unconscious and woke up at the hospital.
To my surprise, my date was sitting right next to me, in training clothes since I puked all over her. She was really worried and just said that we hadn’t had the chance to finish our date. This year, we're getting married.
73. He Got Gassed
My worst date started as a total high school thing: a girl wants to set up a date at her place while her parents are gone for the weekend on vacation or something. So I agree to it, we're having a good time, everything's going well.
It’s starting to get late, we're in bed together, and she totally passes out. She’s out cold, snoring, it’s like 3 am and I'm still awake. Then, she starts moving around on the bed a little…and she lets this toot rip like I've never heard.
It started and it just kept going....and going. At first, I thought maybe it was her little old dog. It wasn't...then it hits me and oh my god, it’s so rank. I pull up my shirt to cover my nose like a mask and in my mind, I'm thinking what the heck did she eat?
To top it all off, she then made this little noise of relief when it was finally over. I couldn't take it. I slipped my pants and socks and shoes on real gently so as not to wake her. As quietly as possible I walked out, down the stairs, and right out the front door. Luckily, she lived in my neighborhood and it wasn't a long walk home.
Of course, the next day she asked me where the heck I went and why but I didn't have the heart to tell her, I figured it would be too embarrassing.
74. Three’s Company
I’m taking a girl to the movies and she asks, "Can my best friend come too?" There goes my chances but trying to be nice, I say, “Of course you can!” She shows up with her friend, who is indeed a guy.
This is when I find out that it’s her one and only ex, but they remained best friends and nothing is happening between them. I think, “Well, this date is ruined, but let’s try to salvage it". I go to pay for our tickets (mine and hers), even when she offered to pay for hers.
After buying, she turns around and buys her ex’s ticket…We actually got along fine and they were nice people, but it was like a tug of war for the rest of the night fighting for her attention. Of course, I lose since they are best friends.
When I get home, the guy adds me on Facebook, and he proceeds to tell me don't bother trying to date her, she's a terrible girlfriend. I finally got her alone for one more movie, but it all just sort of fell apart. I actually really liked her, but clearly, I had no effect on her. Oh well, I guess.
Take note, future daters: movie dates are a bad idea.
75. Clownin’ Around
Perhaps not my worst date, but definitely the weirdest. I was on a date with this girl who seemed great: good-looking, funny, shared similar interests. It was our first date, and we were sitting in some bar that she's a regular at, discussing ourselves when it starts getting to the basic first date questions.
"So, you said you work in an office but is that what you really want to do?" I asked, "Did you go to school for it?" "Actually…” She says, reaching into her bag, "I'm currently going to clown school”. I kid you not, this girl had pulled out a red freaking clown nose and put it on.
Now, if this was our third date, I would have been less shocked. However, we had been talking for a week and this was the first date—we were supposed to IMPRESS each other. But she was good-looking, and I wanted to hook up.
So I said, "Oh! That's so cool. I didn't know clown school was actually a thing”.
"Oh, no, it's competitive!"
"I had no idea. So, are you in clown university, clown college, clown technical school?"
And then she took my joke as an attack. For a clown, she had a terrible sense of humor.
76. There Was No Gray Area
In high school, I went on a date with a guy some girl from my soccer team knew. He seemed like a nice guy, so we went and had coffee at this place in a mall. We were sitting there, and the conversation was alright and then during a moment of lagging conversation he came out with: "I hate couples with people of two different races, it's just not right".
My response was: “Um, I think it’s time to go”. Needless to say we never went out again.
77. She Wasn’t Clear
I once went out with this girl and we were having a good time. We were drinking pretty heavy—mostly Everclear and juice. She suddenly started throwing up like crazy. I was like: "Are you OK? Are you OK?" Her reply was more than disturbing.
She told me: “It's not the drinking, it's because I’m pregnant and have morning sickness”. What is wrong with people?
Freepik,stockking
78. He Disrespected The Gayborhood
I'd had two dates with a fellow I met on OK Cupid that went really well. Both dates had been in his neighborhood and had led to hot makeouts, couch snuggling, and him making dinner for me. I thought we were both fairly interested in one another. On the third date, it was his turn to make the trek to my neighborhood, and I cooked a pretty fancy dinner for him.
He was late to get to my place, and complained about the lack of parking, and then complained about the neighborhood. You see, I'm bi and I lived in Boystown at the time, so yeah it was gay as the day is long but he knew this in advance and his distaste for the fabulosity really turned me off. Worse still, when he finally stopped complaining, he didn't have anything to say at all.
Somehow, the charming fellow from dates one and two had completely disappeared! We sat in awkward silence when he wasn't being condescending or critical. After about an hour and a half he suddenly—and very quickly—bolted. Neither of us contacted the other again. It was bizarre, especially since we'd gotten along so well the first two dates, and I was ready to put out.
79. Equality At Any Cost
I went on one date with a guy I wasn’t physically attracted to because he seemed nice. He spent the ENTIRE date bragging about how much money he made. We shared a pizza. I had one slice, he had six.
When the bill came, he said he’d appreciate it if we split it evenly “because that’s how things work these days”. He tried to make out with me when he dropped me off at home and my god, his breath... it was like he ate a dead raccoon.
80. Got Milk?
A few years ago, I went on a coffee date with a nursing student who described in vivid detail how he and his ex-girlfriend milked an old lady into a toilet at a party. According to him, that was not even the first time or party where he had milked her, he just happened to do it with his girlfriend that time.
I was mortified and found an excuse to promptly leave. The funniest part was a few days later when he texted me asking to go on a second date—which I ignored—followed by another text the next day that said, "It was the milk story, wasn't it?"
81. An Awkward Introduction
I got stood up at a cafe. She called and told me an emergency had come up and she wasn't going to make it. I had only been waiting for three or four minutes and wasn’t too upset about it, so I called a friend to see what he was doing.
I ended up meeting him across town at the bar he was drinking at, which is also where he introduced me to my date, who he had just met playing pool there.
82. Bi The Way
I was hanging out at my house with this guy I had met from work and really liked. We were asking each other questions, just getting to know each other more outside of the work setting. At one point he gets a cheeky look and asks me if I've ever kissed a girl. I’m into both guys and girls, so I reply yes. He looks surprised at how nonchalantly I responded, and pressed further.
When I told him that I was bi, he was silent for a long five minutes. He then silently got up, and just left. Two days later he called me to ask me out on another date. It was weird because he was acting just like nothing had gone wrong. I told him I'd rather gouge my eyes out with a rusty spoon than go out with him ever again.
83. He Wanted To Lead
I am a 20-year-old female and this was my first date—and incidentally my only date so far. You see, I’d recently lost a ton of weight, and I decided to try some internet dating. One of the guys who asked me out said that he had Asperger’s. The thing was that I was socially awkward, so I thought that made us a perfect couple. Boy, was I wrong about that.
So we walked around a little bit together. Now, I'm a terrible conversationalist, and he kept getting frustrated that neither of us could keep up a conversation. I felt terrible, but with every passing minute—the date was less than an hour, I think—my already below-average ability to talk waned. Eventually, he sat down and asked me what he could do better.
I told him that it was my fault, that I'm not used to talking to people, let alone dating. All he kept saying was: “Stop it, I’m the man and it is my responsibility to lead the date”. I felt so terrible.
84. He Got Bounced
I had gone on a really great first date with a guy I had met on the internet. We decided to meet up again, and he suggested we meet when I got off work at the same bar as the first date. I got to the bar and was waiting for him to arrive, so I ordered a drink. Ten minutes later I saw him walking over to me and the bouncer was following closely behind him.
He got to my table and the bouncer said: "No dude, you are still kicked out of here from earlier" and roughly walked him out. So I just stayed and finished my drink.
85. An Icy Encounter
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 took a picture, so my failure was immortalized forever. She took me back to my apartment and ended the relationship before it began. But there's a silver lining.
The woman who is now my wife was at that ice rink on that night. We didn't realize we were there at the same time until a year or two into our relationship and she exclaimed, "You were that guy who couldn't ice skate! Yeah, she didn't seem that into you”.
86. It Took An Hour And A Half
I love to talk and I'm good at keeping the conversation going. On one date, a girl and I took a really long walk, and she wouldn't stop talking. I waited to see how long she could keep talking for without me saying anything. I didn't say a single word for an hour and a half, and there were no silences. I honestly didn't believe that those types existed.
87. Couldn’t Find The Washroom
When I was in college, I went on a date with a coworker. We went to see a movie and then to a mutual friend's house to drink. We decided to go back to her parent’s house to chill after. Since I was quite inebriated, she agreed to let me stay the night. Apparently, in the middle of the night, I got up and peed on her dog’s bowl and all over the kitchen floor.
She cleaned it all up and told me about it the next day at work. Four years later: we got married.
88. It Was Immortalized Forever
Back in college, I was invited to an ice rink with a girl I liked along with 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.
It turned out I had fallen right at the moment someone took 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 at that ice rink on that night. We didn't realize we were there at the same time until a year or two into our relationship and she exclaimed, "You were that guy who couldn't ice-skate! Yeah, she didn't seem that into you”.
Freepik,wayhomestudio
89. She Could Do So Much Better
I went out with a musician on a blind date once. He talked about himself non-stop for an hour and when I mentioned casually that I like things like Reddit, Star Wars, and fixing computers he called me weird. He said, "You can't be a computer nerd with that pretty face. You could do so much better”. I told him that I completely agreed that I could do better things with my time. I then stood up, excused myself, and left.
According to a mutual friend, the guy never understood what I meant by that comment and was super angry that I left him with the bill, which was a couple of bucks for a soda. I don't usually expect guys to foot the bill just because they're guys, but I later explained to him that if he was going to ask me out and then insult me, he's lucky he only paid for a soda.
90. Bragging Rights
On our second date, he bragged to me: 1) how long he was able to stay on unemployment, 2) how he was always able to talk his mom into letting him come home after she kicked him out, 3) how he basically paid for the $3,000 implants of a dancer, even though he didn't get anything for it.
He also revealed that he got locked up for about four months for pulling a pistol on some teenagers, but he didn't intend to use it. This was a half-brag, not a full brag. It was so strange because he seemed like a nice guy on the first date.
On the second date, with all of that, I was just laughing inside and wondering how I was going to end the date. Turns out it wasn’t a problem because after dinner he had to go and hang with his buddies at the video store.
91. Laying All Her Cards On The Table
My worst date? She had Crohn’s disease. She takes her pee bag out in the middle of our dinner date and says I need to look at it so I understand what I’m getting myself into. The catheter tube knocked over her drink. It was awful. Poor girl.
92. Momma’s Boy
For our first date, he took me to dinner at his mother's…with his brother and the mother’s crazy housemate. After dinner, we watched Iron Chef with all of them while sitting on the floor because there weren’t enough chairs. During the show, his mother was talking to us about using vibrating toys when doing the housework to make it more enjoyable.
And here’s the best part: He didn't even live with his mother. Needless to say, it was our first and only date.
93. Don’t Play It Again Sam
I had been in a relationship for two years in high school. We broke up, and I just started dating a distant friend of the ex. We had been dating for like two weeks, which was mostly just me driving him around and buying him breakfast before school. He had me in his car in the parking lot after school one day because he said he had to talk to me.
So, I'm sitting there, and he says, that he wants to sing me a song. He then pulls out this piece of paper with the lyrics to Kasey and JoJo's "All My Life”. He starts singing the "baby, baby, baby, baby, baby" in the beginning. I suddenly yell at him to stop because that was my ex and my song. His reaction was unforgettable.
He gets embarrassed and ends up eating the piece of paper. Like, crumpled it up, put it in his mouth, and swallowed it. It was so weird.
94. She Was Traditional
I once went out with a girl, and five minutes after sitting down at the restaurant she says, "I'm a little old fashioned and think guys should always pay for everything when they are dating a girl”. I had planned on paying but having her so blatantly state that so early on, I was pretty angry and realized the date was already a total bust.
Since the date was going nowhere, I decided to have some fun. I told her that the reason that guys traditionally paid for everything was that back in the day, women weren't allowed to get real jobs. So, to further this return to the “good old days”, I told her that I would also be ordering for her since that was traditional too.
95. Like Jekyll And Hyde
I once drove two hours to see someone I had been talking to for almost a year online. When I got there, I was in for a horrible surprise. I found a much younger man than he’d said he was. Also, he was living in the back room of his parents’ house. It was like a back porch, and his bed was a couple of blankets and pillows on the floor next to the washer/dryer.
Once we were off the computer and in real life, conversing with him was like talking to a wall.
I had arrived at his place really late, so I went to sleep when I got there. The next day we went to his local—to be honest quite run-down—mall and he met up with a friend and ignored me the entire time. I eventually got annoyed and left. When I got home, he talked online like he did before we met: all sweet and saying he missed me—nothing like he was in person.
I told him I wasn't interested and every few months for the next year or two he would try to talk to me. Ugh.
96. The Ole Switcheroo
My worst date started off as a date and ended up as an MLM pitch. On the plus side, I still have those Cutco scissors and they are decent.
97. The Stench Of Success
It was my third date with a girl, and we went to a Poison-Def Leppard concert. We weren't eating before the concert and I was starving, so I grabbed a chicken salad sandwich from a gas station before I picked her up.
Halfway through the show, I have to poop. Bad. I run to the can and every toilet is knee-deep in filth. We had VIP seats, so I figured I would wait and hit the VIP bar on the way out. I took a massive dump and made five guys scream about the stench, which made me giggle.
Well, we parked in front, pulled the car out, and sat and waited. All of a sudden, round two hits—and this time it is wet. I was getting stomach contractions every 2-3 minutes, I was death-clinching the steering wheel and sweating like a fat lady in Golden Corral.
I then had an epiphany that if I just tooted a little, I would feel better. Oh, how wrong I was. The soft serve ice cream machine in my shorts exploded and got everywhere. I ran into the woods, finished pooping, and wiped my butt with my wifebeater.
We have been married 12 years now and have three kids.
98. Showing Off His Creepy Side
I once browned out at a club and remember briefly meeting a guy in a suit. The next day, I woke up to a text from Willis, the guy in the suit. Turns out we both didn't really remember each other. Over text, he seemed nice enough and we both thought it'd be a funny experience if we went on a date.
We met up for lunch and upon meeting him, I didn't really have much hope for a second date. He was kind of awkward and tried a little too hard to stunt. But whatever, he seemed like a nice guy. We sat down for pizza and started getting to know each other.
I told him I was studying public policy and was delighted when he asked what kind of policy I wanted to focus on (most people don't really care). I went on a whole rant about how much I wanted to make education policy better because I thought education had the potential to dramatically change lives, especially for those not born into much.
After I finished my rant, he says, "That's cool but I don't really believe in education for low-income people because when I grow up, I want maids and butlers and, like, someone has to do that”. I responded, "Some people have that viewpoint," and started to look for ways to end the date. But the worst was yet to come.
After we finished eating, I made up an excuse to leave an hour earlier than planned. He asked if I really had to go and said, "I should just kill you and keep you with me”. Smooth. I told him he probably shouldn't joke about that. He responded, "I would bury your body right there haha”.
I hailed down a cab after that.
99. Just Pop A Squat
I was in France and having a lovely dinner at a sidewalk cafe with a young lady I met the day prior. But in the middle of our dinner, she did something utterly deranged. She excused herself to use the restroom, got up, walked about ten feet, squatted, and peed in the gutter. Yup, no second date after that.
100. White Lotus Season Three?
My friend and his girlfriend invited me on a three-day weekend getaway. Not wanting to be a third wheel, I invited my platonic female friend to join us. That turned out to be a huge mistake. My friend ended up breaking up with his girlfriend within hours of the four of us arriving at the hotel—and he did it in front of all three of us. She was crushed yet she still had to spend the entire weekend with him.
The next day, things got even worse. He proceeded to hook up with the friend I had invited. Right in front of his now ex. The poor girl was just trying to recover and save any shred of dignity she still had. It was, without a doubt, the most awkward weekend of my life. I spent the whole time comforting her and giving her a shoulder to cry on while he proceeded to throw his hookup in our faces.
I think Karma worked its magic, though. It has been five years since that weekend and he’s single, miserable, and depressed. He hasn’t had a steady relationship in years and she is happily married.
101. Almost Lost Her To A Pea
In 2004, I was dating this girl in my first year of university. I was definitely punching above my weight as she was gorgeous and also a year older than me. I never really got jealous of other guys trying to talk to her, because she would always pull me beside her when they did.
One night, however, we were at the student bar, and I didn't see her for quite a while. One of my friends was like, “Bro, your girlfriend’s totally about to cheat on you tonight". Now, I went looking for her...and what I saw has stuck in my mind.
Here I was: 18 years old, at a small student bar in New Zealand, and there was my girlfriend getting friendly with will.i.am from the Black Eyed Peas. He ended up just giving her free general admission tickets to his concert and bailed with his security guards before they did anything.
102. Scene And Heard
I needed to catch a bus. The entrance of the university to the bus stop was a mile away. I was breaking up with my girlfriend in public to make sure she would not make a scene, but it totally backfired. She made a huge scene and begged me to stay with her, but I refused. She stalked and followed me, begging, crying, and yelling in front of around 30 strangers.
Once I got to the bus stop, she tried to push me in front of a running bus. I yelled at her, "Are you trying to kill me?" She responded, "I want to if you are not with me". Then, she proceeded to break into my house. She filled it with photos of us.
Later, she called me several times, screaming that she was going to take her life. Then, she tried hitting on my friends and managed to make out with my ex-best friend.
103. Bait And Switch
When she responded to a “Hi” on Tinder with something like “hey cutie, want to come to my parents’ house?” We chatted for a bit, and according to her she wasn’t looking for anything serious but she wanted me to pick her up, take her out to dinner, and maybe get it on afterwards. Very transactional, which kind of stung but whatever she was hot.
I looked up the address she gave me. When I read it, I got a small, dark feeling. I was surprised to find a neighborhood I did some work in, and that the house was one I knew was for sale. Specifically, the owner passed and it was being gutted to be resold by his kids. At this point I was 100% convinced this was a scam, but somewhat curious, I decided to drive by and see if anyone was there.
I texted her I was coming, but in a different type of car. It was a really expensive neighborhood on a sea-cliff, and it felt like an adventure. I took my work truck. I drove by and some huge dude comes out of the house, stares at my truck, and goes back in. I could see other people inside. I noped out of there super fast. Pretty convinced it was a phishing scam to mug me, or a prank. Didn’t feel like finding out.
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104. I’m Gonna Getcha
I was dating this girl who asked me to go to her ex’s wedding. We dated for a few months prior, but asking me to go to a wedding together felt like a serious commitment...I still accepted. I planned for the week off work and we went all out for this wedding. Half the time, I was trying to make the most of our time together, but she always went missing.
Fast forward to the reception. She made a scene in the most unstable and mentally sick way. In front of the groom, the bride, and everyone else, she said out loud: “I’m still in love with you. We literally have been sleeping together all week and I can't stop thinking about you". She quickly got escorted out after that.
The bride was clearly upset, but everyone tried to go about their business. As soon as I left, my “girlfriend” started completely ruining the hall and all the decorations, just throwing a fit on her way out. It was so embarrassing. I figured she was telling the truth since she was missing the whole time, but I’m pretty sure that everyone during the whole thing assumed this was too crazy to be real.
I definitely regret not seeing her true colors before, but when you work so much and try to date at the same time, you have very little time to get to really know some people. Time sort of flies by and you end up dating for a few months. Fast forward a month or two later...she got together with the groom and I’m pretty sure she has no regrets about wasting my time.
She probably doesn’t even feel bad about using me or even ruining that man’s marriage. This woman is seriously twisted.
105. The Worst Kind Of Deja Vu
A year and change ago, I had just gotten out of a bad relationship that I had broken off. I'm a driven person, and my work is what drives me. The relationship wasn't great, so I wasn't that torn up about having to end it. Several of my friends who don't know me that well assumed that I was super depressed, because I wasn't partying and going out as much as I normally do.
In reality, I just had a HUGE grant proposal to work on, which is a real pain in the butt and takes a lot of time. The relationship I had been in wasn't serious, and it was only for a month-ish "unofficially" so it really wasn't a big deal. She's a weird one, so I was in the middle of introducing her to my extended friend circle when things broke off.
My friends came up with this whole plan of meeting me somewhere and then not showing up, only to have me find out it was a blind date. So they did this, and called me right when I was outside the sushi joint to let me know. After getting angry, I figured what the heck, why not go in and share a meal with a stranger, what could happen, right?
Imagine my surprise...when the girl I had just broken up with was sitting there waiting for me.
