If love lifts us up where we belong, bad dates plummet us right back down to earth. These dating horror stories made us cringe, laugh, and weep for humanity, but most of all, they made the cat lady lifestyle look dang good. From meet-uglies and painful first dates to awkward breakups and online dating horror stories, we can’t look away from these dating trainwrecks.
1. Bad Math
I offered to pay for the bill. She insisted to pay half. I didn’t fight it, but I only had a large bill so I did some mental math, pocketed her money and put my bill in. Anyway, long story short, I did the math wrong and ended up stealing 20 bucks from her. She sarcastically said, “thank you,” and I thought she was being sincere. I’m an idiot.
2. The Last Dance
The guy played Dance Dance Revolution for a good 45 minutes while I just stood there. I left and played a couple arcade games by myself, then came back and he was still playing. But it got worse. On the car ride home, he asked how many children I wanted and started suggesting names for “our kids.” Then he tried to make out with me when I got home. Nope goodbyeeeee.
3. A Hairy Situation
We’d just left the restaurant after a really nice date and I was wondering who’d make the first move. My date, who was very cute, told me my hair looked nice. I figured now was the time to strike so I flirtatiously said, “Bet it would look nicer with your hands in it.” He replied, in a very confused tone, “…You want me to style your hair?” There was not a second date.
4. Brotherly Love
I went on a date with a girl who I met online. All throughout the date, she kept looking over at me and then laughing, but not really in a mean way. After a while, I called her out on it and she basically said, sorry but you really look like my brother. Then she shows me a picture and lo and behold, she’s absolutely right. He looks more like my brother than hers. I still can’t figure out why she agreed to go on the date in the first place when she could tell this was the case from my profile pic.
5. It’s-a-Me, Dustin
The guy faked an Italian accent the entire time. He was from Florida.
6. Moving Too Fast
I went on a date with a guy named Dan when I was in my late teens. Dan said, “I’d like you to meet my father, he’s going to love you.” So I got in the car and as we started heading out of town, I asked where we were going. Dan said, “you’ll see, we’re almost there.” 15 minutes later, we pull in to a cemetery, and he says come with me.
I was nervous as I followed him down a little hill and he kneeled down in front of a tombstone. He said, “Dad, meet shortcakie, she’s going to be my wife someday.” That was the first and last date Dan and I ever had.
7. NOT the Kind of Biology I Was Looking for
We went back to her place. She thrust a model of the cell in my hands and asked if I could name any of the parts. I got the membrane, nucleus, ribosomes, mitochondria, cytoplasm…at that point she ripped it out of my hands. I guess I was supposed to not know them?
8. Having a Gas
It was around date three and me and this girl were grinding with clothes on in bed, running hands all over each other. I put my hand over her throat, which unfortunately triggered a panic attack for her. I, in turn, panicked a little and did the only thing I could think to do—the very thing I had been desperately clenching my butt cheeks to try not to do. So I blurted out “DISTRACTION” and passed gas.
9. Mousy Girl
I went on a date with a girl who revealed that her hobby was buying dead little mice, doing taxidermy on them, and then dressing them up in tiny little metal battle armor and swords to stage historical battles…using dead mice…that she bought online. She showed me lots of pictures before the date ended.
10. An Old One and Not a Good One
This was in high school. She invited me to her house to have dinner with her family and I didn’t know them very well yet. The conversation turned to names we thought were old-fashioned and ugly-sounding. We all threw out a few like Gertrude, Bertha, and Eugene, and then I said the one thing that ruined everything.
I said, “At least that one’s not as bad as Deborah!” I used my ugly voice and everything. Her mom’s name is Deborah. Her grandmother was also at the table with us.
11. Couple Seeking a Sugar Daddy
I showed up to an Internet-based date and she showed up with a dude. She expected me to pay for both of them to eat and drink for the evening.
12. Groundhog Date
It was my second date with this guy and he said the exact same things that he said on the first date—word for word. The same stories, the same “random thoughts,” the same questions. It freaked me out so much that at first I played along and answered in the exact same way, as though we were both following some weird script.
Eventually, I tried to break the mold and ask him new things, but he would just bring it back around to the same topics as last time. It was like I was in a computer program and there was a glitch. It still freaks me out to think about it.
13. Sweet Disaster
We order a small snack for our coffee and as it’s arriving at the table, he pulls out his Nokia phone. Trying to make a lighthearted joke, I say, “MAN, that has got to be the oldest phone I’ve seen in a while.” I really dug it in, trying to break that awkward first date wall. Well, it turns out that it was not a Nokia, it was something much more embarrassing. It was his insulin pump.
14. Britney Moment
I once had a girl get up and go to the bathroom during a make-out session. When she came back, my jaw hit the floor. While in the bathroom, she had shaved her head. I will never know why.
When my boyfriend and I had just started dating, we were laying down watching a movie, but this was a small bed and he was being respectful and trying to give me space. I kept wiggling backward so I could get closer to him, and he kept inching backward too, since he thought I was just trying to get comfortable and he was in the way.
He ended up sitting in a chair next to the bed. Three years later, we are still together, and I still think it’s pretty funny.
16. Bad Omens
I matched with a girl on Tinder. We hit it off in conversation right away and arranged a date at a tea place. We get there and the conversation seemed to be going alright—until she asked me if I was fine with her doing some drawings. She proceeded to draw the four horsemen of the apocalypse, calmly asking me what my thoughts were on them, the end of the world, the devil, et cetera; aside from that, the time was spent in silence.
17. Please Tell Me It Was a Lincoln
My aunt dated Matthew McConaughey before he was famous. He ended up getting invited to her wedding to my “normal” uncle and proceeded to pass out drunk in the back of my family’s car. He refused to leave, and now my dad refuses to watch his movies!
18. A Special Guest Appearance From…
I had a mid-40s man with a young and attractive mid-20s woman sitting at the bar. They were engaging in small talk and ordering drinks, nothing out of the ordinary. After possibly 45 minutes, a lady storms into the bar and immediately goes up to them. She grabs the man by the shoulder and says, “You…You’re a [c-word]” and walks out.
The man turned to his perceived date and says, “Yeah, she does that,” and then left the room, leaving his date to sit there, staring blankly into oblivion until she left. Odd.
19. The Wonders of the Cosmos
This was around date three with a guy who was as dense as a brick wall. All he’d do is hold my hand, so once we got back to my place I literally undressed in front of him and undid my hair. Then proceeded to tell him I was taking a bath, and I lit candles and shut the lights off. He followed me in, got my hopes up, and then sat fully clothed on the toilet talking to me about space. For 30 minutes.
20. Thank You, Next
The date had been going great. It was possibly one of the best dates I had ever been to up until the point when he suddenly asks me if I wanted to use my hands on him down there. I awkwardly laugh it off and say that I don’t really know him well enough for that. Then he gets all quiet and seems really angry. It ended with me just going, “There will not be a second date, bye.”
21. Nailed It
I still have nightmares about this date. When I was about 20 or so, I got a date with a girl who I really liked, she was exactly my type and I couldn’t believe my luck. We met in a local pub for a few drinks and things were great. I was getting all the good signs with lots of hand touching and the like. An hour of pure bliss went by and I needed to pee.
After washing my hands, I went to the hand dryer only to find that it didn’t work. I wanted to dry my hands because I wanted more of the hand-holdy stuff. Then I had the single stupidest idea of my life. I thought, “I can fix this!” and put my hand inside the nozzle of the dryer. WHY!? WHY!? Obviously, I got buzzed by the electric heating element, fell back, and cracked my head on the wall.
I didn’t get knocked out but I needed a few minutes to sort myself out before going back. I didn’t have the guts to tell her what had happened; dumb idea number two. I had a banging headache and I wasn’t quite right. Not much later she made her excuses and left and turned me down when I asked her for a second date. A year or so later I found out she had told her friend that she really liked me, but I went to the toilet and came out acting really weird and she “wasn’t up for dating someone on drugs.”
22. An Awkward Coincidence
On my first date with this cute girl, we started talking about tattoos. I have a rule that if I have an idea for a tattoo, I sit on it for a while to see if it’s something I truly want. I mentioned this to her and explained how glad I am that I do this because otherwise I’d be covered in Tool (the band) tattoos or some, “other dumb stuff.”
Little did I know, I’d just messed up big time. She rolled up her sleeve to show me that she had the lyrics to one of their songs tattooed across her arm.
23. The Great Shoe Heist
We had a great date that ended with a walk on the beach. I took my shoes off and he offered to hold them while I grabbed a couple of seashells. We walked back and while I’m washing my feet off he walked over to his car. I thought he was going to grab a towel but instead, he took off with my shoes!
24. It’s Not Technically Cheating
I had just moved to London and met this guy on a dating website. He was generally not my type, but still, I was trying to meet new people so we go on a date. As we settle into the restaurant, he takes a call from a girl and says to her, “Oh, I’m just in the pub with—male roommates name.” I can hear her on the other end getting worked up about something and him telling her to calm down.
Alarm bells are already ringing. He hangs up the phone and says, “That was my fiancé, but not a real one, just one I’m with for her visa.” At this point, I’m already thinking “bloody hell.” He continued on with his excuse, “She also lives with me,” in his two-bedroom apartment with this other roommate—cozy. “Oh yeah, I should probably tell you I’m getting married in three weeks.”
At this exact point, I just said, “Well, I’m going home,” and start pulling on my coat. His reply was even more classic: “Do you want to help me buy groceries first?”
25. Wrestling With My Feelings
I was talking to dude on a dating app and we decided to meet up for coffee one day. Our coffee did not go well. He only talked in impersonations of WWE wrestlers and then asked me to go to wrestle mania with him and his entire family later that night.
26. Worthy of a Twitter Thread
I met a girl on Match. She showed up 20 minutes late. I had to “excuse myself” so I could hide out in the bathroom and write down as much of the crazy things this woman was saying before I forgot. Topics included, but were not limited to—Daddy issues, her mother loves her brother more, miscarriage, being married before, when “we” start dating—but it didn’t stop there.
She continued and talked about what would happen when “we” are married, setting me up with her assistant, how she’ll “screw me with blood on my face,” things she does when she’s high, Brazilian trance music, adopting children, what’s my dog’s name is again, how she doesn’t trust animated movies, why she was 20 minutes late, owning a business, when it’s acceptable to use the c-word, being a vegetarian, her blind cat, her dying uncle, abusive relationships, the city of Tampa, free-range urination, and can we order tater tots.
We didn’t go out again.
27. Hesitant Eavesdroppers Almost to the Rescue
This one guy didn’t let me order on a lunch date at a cafe because “girls don’t really eat anything for lunch anyway.” So, I drank water while he ate a family-sized pasta dish with his mouth open while talking constantly about fashion. I actually had fun listening to the two women at the table next of us be horrified about how clueless he was and how bad the date was.
They were clearly trying to figure out the best way to rescue me from him. They didn’t rescue me, but I magically got “a text”and needed to leave.
28. Quack! Quack!
It was the first time that my boyfriend met my family. We were going to a family event at a pretty swanky hotel. He was wearing an old suit and he’d recently lost the skinny chicken legs he had when he wore the suit last, due to working out. I remarked that the suit looked a bit tight around the leg region, but he didn’t listen. Big mistake. We got talking to one of my cousins and everything was going fine until my fiancé dropped his wallet on the floor.
He squatted down to pick it up and immediately, the loudest ripping sound you have ever heard ensued. People actually stopped their conversations and turned to look at what had happened. He ripped his pants from his crotch all the way down to his knee. But it gets worse. He had chosen THAT DAY OF ALL DAYS to wear a pair of boxers that had a picture of a duck with writing that said “Butt Quack” on it.
There was no coming back from that. The whole room was silent as we walked out.
29. Chivalry Is Dead
I dated this wacky woman several years ago. She was very big on chivalry, but I hadn’t realized it until our second date. I took her to a restaurant and she excused herself to go to the bathroom. I had my back turned to her, so I couldn’t see when she was returning. When she got back, she was upset that I didn’t stand up upon her return.
She then listed all of my missed opportunities to prove to her I was chivalrous (didn’t open her car door, didn’t bring her flowers, etc.). Then she sighed and said, “I’m not sure if you’re going to be a good role model for my son.”
30. Speed Dating
My first dating app date. Starts off pretty good, but we barely put in our dinner order and her phone starts blowing up. Her ex was drunk and causing a scene outside her apartment. Her ex kept calling, then her roommate started, and then the landlord calls threatening to call the police. We get our food to go and I take her back to her apartment.
Long story short, both she and her ex are crying messes, she goes inside, leaves me outside with crying drunk ex, who starts telling me all about how he messed up their relationship. Dude is way too drunk to drive, so I end up driving him to his apartment, Uber back to my car, realize my date took all the food with her. The joys of dating!
31. Don’t Mention the Carl
I had been flirting with a girl for a few weeks and finally asked her out to coffee. Things were seemingly going well. Somehow squirrels come up and I mention casually, “my friend Carl likes to shoot squirrels in his backyard. He taught me how to shoot but I was never good enough to hit such a small target running across the lawn.”
Her response was, “Ummm, well it’s getting late.” And that’s how the “Don’t mention Carl” rule got added to the list of things I am not allowed to do on first dates.
32. Life’s a Picnic
The weirdest was when I was a college junior and dated a girl who was a classmate. She wanted to have a “picnic” in a cemetery for a truly dark reason. It was at the gravesite where her ex was buried, as he had been killed in a crash two years previously. I told her that I’d accompany her to visit his grave, but that picnicking and having a good time there somehow didn’t seem appropriate.
33. Call It in
I went for a meal with this girl I met through a dating app. We started talking about movies and since the date was going well, we decided to go watch Inception. But as we walked inside, I realized I didn’t have my phone in my pocket. I tried to go back to the car to check for it there, but my date kept saying we’d miss the movie if we went back. The phone was brand new so I insisted we go. We checked the car for about 10 minutes but we couldn’t find it.
A couple parked next to us so I asked them to ring my number. The phone started to ring and it was obviously coming from my date’s handbag. She took it out and said she had no idea how it got there. I thanked the couple and as I turned back around she was walking the other way. That’s when I realized it wasn’t an accident and just left her to walk home alone.
34. Cat Conversation
It was a speed date. He talked about his dead cats, all of them from his past, for the entire five minutes or whatever. I’m not sure he knew my name.
35. Beware of Child Stars
I dated a former child star for a short time (he was in his mid-40s at the time). It was super SUPER not fun. He wasn’t a child star who’d moved on to fame as an adult like Jodie Foster or Ron Howard – after age 15 or so, he just became a regular guy and he couldn’t handle it. (And no, I’m not saying who it is. I want to keep that aspect of it private, so please don’t ask me). Among the many things:
- First of all, his house was a shrine to the show he used to be on.
- He was a semi-celebrity in the small town he lived in, so on this one wall of a local restaurant, they had a framed picture of the cast of his show that he’d autographed. And if we couldn’t get a seat at the table near his photo, he’d get all mad.
- One night, he dragged out this big shopping bag full of fan mail he’d gotten when he was a kid, and we had to sit and read through it.
- He would lie in “Where Are They Now?” type interviews, and say that he was just SO grateful to have a normal life, that he was SO glad to not be famous anymore, that he’d see the huge level of fame for someone like Brad Pitt, and just “feel so sorry” for them that they can’t have a normal life. But in reality, he desperately wanted fame back. There was a supermarket opening in his town, and they asked him if he’d go to it, and he said yes. I was embarrassed for him – I was like, “Don’t do this. Just be a normal guy, please don’t embarrass yourself at a supermarket opening.”
- He got an invite to one of those “Where Are They Now?” has-been fan fests. The organizers made it clear that they only wanted him AND one of his co-stars, who didn’t want to do it, because she actually had moved on and actually did have a totally normal life. He called her up and just pathetically begged, near tears, for her to please, please, please go to this with him, that he needed her there with him because they didn’t want just him. She said, “Ehh, no, dude – you know, then I have to take my kids out of school, book plane tickets for me and my family, pay for a hotel room, etc., and for what? To make a few hundred dollars charging for autographs?” So, she wouldn’t do it, and he freaked out on her over the phone.
- There was another child actor who was on a show that was much, much more popular than the one he was on. They were about the same age, but it was a totally different level of fame. So, this other actor, as an adult, briefly starred in a new television show. It was totally boring, but of course, the guy I dated made us sit and watch each episode, every week. And he’d sit there and literally say, “Why him? Why not me? We’re about the same age. We were both famous about the same time. Why did HE get this break and I didn’t.” Which made his interview about how he was “SO GLAD” to not be famous and have a normal life so much more pathetic.
36. I Only Love Myself and My Mama
The guy talked and talked and talked all evening about himself, his parents’ divorce, his ex’s bedroom preferences, and his depressed best friend. And he joked about murdering me. At the end, he told me he lived at his mom’s, but I can come by if I want to.
37. Silence Isn’t Golden
It was supposed to be a coffee date. I got there on time, and he had already ordered and drank his coffee. I went up to get mine, and he just stared at me from the table while I was ordering. The date itself lasted about two hours, and I honestly can’t remember a single thing we talked about, because he wasn’t contributing to the conversation at all.
There was one point where I was just staring at him and I remember thinking, “If he doesn’t bring up a topic of conversation in the next 30 seconds, I’m leaving.” Dude genuinely just stared at me. Maybe he was trying to communicate telepathically, I’m not sure. When I tried to leave, he insisted that I stay. Why???? We haven’t talked about anything and it’s been two hours! Weird guy. I did end up going on a second date with him, but it was just as awkward. Called it quits after that.
38. Three up, Three Down
I have had three separate dates with three separate women that all turned out to either be Christian revival meetings or Young Life. C’mon.
39. No Need to Be Catty
This was during my hot mess college phase. I got very drunk on a date, blacked out completely, and then puked all over my then-boyfriend (now husband)—as well as the washroom and bedroom. I woke up wearing fresh clothes. He explained everything that had happened after me begging him to tell me. When he finally did tell me, it was so embarrassing that my face went bone white.
Apparently, I started trying to exorcise demons out of him and just projectile vomited everywhere. He managed to get me to drink some water, bathe me, get me to bed, and then deep clean the room and washroom. I was so embarrassed after. The only memory I have of that night is his cat looking at me with concern and judgment.
40. Demon Dogs and Bitter Words
My parents have an extremely ugly little dog. Like, this thing is unfortunate. It’s basically a cross between a Chihuahua and some sort of lesser demon with buggy eyes, an underbite and just plain ugly features. Strangely enough, this little creature adores my boyfriend. One day, he came into my parents’ house from work (I was already there) and the ugly dog runs up to him like she just won the lottery.
He scoops her up, laughing and completely without thinking he says the cruelest thing I have ever heard: “Why is it that only the ugly girls like me?” There was dead silence and his expression faded in slow motion. I said nothing, just got up and walked outside, the sounds of his pitiful groveling and apologizing following me. I know he meant nothing by it, but to this day my family doesn’t let him live it down. He definitely paid for the faux pas.
41. At Least He’s Upfront?
My date got wasted and confessed he was looking for an older woman to take care of him financially, shouted and slurred in my ear that he was a very sensual lover—much to the amusement of the people next to us—and desperate to have children very soon. Weird.
42. Grocery Boy or Boyfriend?
I met a girl who was a friend of a friend and we swapped MSN Messenger details. We talked for a couple of weeks, got along great, and I suggested meeting up again. She was keen. Instead of going for a coffee, as I had suggested, she took me to a grocery store. She needed help picking up groceries for her Scouts for a camping weekend.
Basically, she had asked me out so I could help her load two full shopping trolleys of heavy stuff. I helped her load it into her car, thinking maybe we were going to drive somewhere to chat, or whatever. No, she just said “thanks!” waved at me, and drove off. On MSN that night she asked me if we were now boyfriend and girlfriend. I explained that we’d have to start dating first.
43. I Thought I Was Being Smooth
My first night in Buenos Aires. I’m in a nightclub buying a drink. I hand the bartender about $20 in their currency. He’s saying something in Spanish I don’t understand. But I’m thinking one drink can’t cost more than $20 so what’s his problem? This incredibly smartly dressed, beautiful woman intervenes. She explains the barman is asking if I have a smaller note because he doesn’t have change.
No problem. We get to talking. I tell her it’s my first night in the city. She says, “Oh, you must let me show you around town tomorrow.” She puts her business card on the bar and pushes it towards me. It has her name, her number, and the fact that she’s an English Language Teacher. Then I mess everything up. In what I think is an incredibly witty, flirtatious comeback I pushed the card back towards her and say, “oh, I don’t know. My English is already pretty good.”
She scoops the card back, says, “fine,” and walks away. I remember think, “Oh well, at least no one saw that.” Then I turned around and my friend is right behind me shaking his head like “What a loser.” But it somehow gets even worse. When I told that story to some Argentinians I met later in that trip, they said not to worry. The woman had probably been a con artist targeting foreign tourists.
44. Unlock My Meaning
I went out with a really cute guy. We had a good date, had ice cream, went to a movie. He dropped me off at my house. He had his freaking hand on my knee, I kissed his cheek. I tell him, “I don’t think anyone is home.” He replies, “I hope you’re not locked out!” I don’t know how much clearer I could have been that he could slide into home base.
He texted me a couple days after that, but I don’t know, the spark was gone.
45. Don’t Assume
I’m a straight man who accidentally went on a date with another guy. We met because we live in the same apartment block and after we started chatting, he asked if I wanted to grab a beer. We were having a good time, until my girlfriend called me on the walk home and I saw his face face. I realized he’d assumed I was gay and that I’d assumed he was just a friendly guy wanted to hang out.
46. Mixed Messages
I matched with a Chinese exchange student on Tinder. She asked me to meet her at her apartment, then we’d go link up with some of her friends at the waterfront. We’re texting as I’m on the way over, and she says she didn’t realize this was a date. Nonetheless, she asks me to pick up dinner for both of us on the way over.
I get to her apartment, and before I can even take my jacket off, she says, “So, do you have anything to say to me?” Presumably because I’d spent 15 seconds in silence. I offer her the food she asked for, she said she wasn’t hungry. I try to strike up a conversation, but she dead ends every topic I bring up. She starts texting and making phone calls.
She was speaking Mandarin, presumably, but I was able to make out the name of the place we were supposed to meet her friends. She said something about how plans might change because her friend needs help. Throughout all this, I just sat by myself, eating my sandwich in silence. When I was finished, I asked if she just wanted me to leave. She said yes, then gave me $20 for dinner. Girl straight up used me for food delivery.
47. Pebbles or No Bam-Bam
So I was 18, in the Air Force, and living in the dorms. My roommate set me up with his girlfriend’s cousin, and the four of us went to a movie. There was just one thing: she brought a stuffed animal. Not a tiny little thing some (young) women clip to their keychain. It was a gigantic blue rabbit at least as big as a toddler. She said she brought it because she sometimes gets scared in movies.
We were seeing a comedy. After the movie, we grabbed some ice cream and drove the cousins home. My date then invited me to kiss her at the door, but told me I should also kiss “Pebbles” the stuffed animal so he wouldn’t be jealous. Of course I kissed Pebbles. My date was actually out-of-my-league hot. But straight-up crazy.
48. Woah, Woah, Woah Now
The first time I ever used Tinder was also my worst experience with Tinder. The date itself was fine—a little stiff—but fine. Typical questions like what are you studying, where did you grow up, etc. We ate dinner and I didn’t plan on meeting up with him again.
The next day I got a text from him saying, “Hey.” I text him back “Hi.” He asks me what’s up, I say not a whole lot what’s up with you… End up getting a HUGE paragraph back talking about his creative process for writing (and trying to direct) a specific type of adult film where women crush rats and tarantulas between their breasts. WHAT THE HECK!
49. We Fell Hard…
This was early in my dating days, so I can claim awkwardness beyond human reason. It was my first date with a guy who’d I’d known and crushed on for a while before we mutually agreed we should give dating a go. So, naturally, the whole hanging-out-with-the-intent-of-romance didn’t exactly go smoothly. It went horribly, actually.
When the “moment of magic” came at the end of the date, he bobbed left, I swooped right, and he managed to fall down some steps and I fell in a bush. We called it at that and there were no more dates.
50. Guessing Game
Went on a first date where someone asked me why I cut my hair so short. I guess I could have lied or blown off the question, but I don’t like to start anything with falsehood, so I told him the awful truth. I had chemo for breast cancer. I said that I’ll probably be completely fine now, and we absolutely didn’t have to talk about it.
He asked me a few questions about the surgery (single mastectomy), and he said “I wanna know which one it is, but I can’t look at your boobs NOW!” I told him if he could guess which boob got the axe, I’d buy the drinks and appetizer. He won, and I never saw him again. I’m positive I am the weirdest date THAT guy has ever been on.
51. Bleeding Heart
I have volatile allergies. My nose may have started bleeding during a New Year’s kiss with a beautiful girl I met that night. It may have gotten in her mouth by the time we noticed. And I guess she maybe ran to the bathroom and threw up. Please don’t look at me.
52. Fake It Till You Make It
I went on a date with a boy when I was about 16. Anyway, he was older. I lied about my age and even though I literally looked 11, he still believed me—super dumb of me, right? He was in his 20s. “Let’s get a drink, yeah?” Me being too nervous to tell the truth, I agreed. Flash forward and we’re outside of the bar. It’s our time to go inside and the bouncer checking ID asks me about mine.
“Uh, sorry, I must have left it at home”, I defensively exclaimed. He knew I was lying and I did too. My date looks at me weird and he starts interrogating me. I literally cracked with embarrassment. I started sobbing and at that point, I tried to run inside the bar like I actually had a chance. I even threw a tantrum causing a HUGE scene. Way to show my true age.
After, he looks at me with a blank expression and I honestly was crushed. We’re in the car leaving and at this point, it was nothing but silence until he was like, “Let’s go somewhere age-appropriate then.” “Age-appropriate?” I was shocked, as he wasn’t even mad at me. I didn’t know what to do with myself. I just sat in the back of the car, mentally beaten.
We drive for a while and I honestly thought I was going to get kidnapped. Then eventually, we pull up to a Chuck E. Cheese, and he leaves me there.
53. Have You Ever Kissed a Human?
He leans to kiss me just before I board my train and there’s the “kiss” that scarred me forever. He had both my lips in his mouth, sucking them, then he just stood there like that for a couple of seconds before releasing the suction. I was shocked and I quickly said bye and boarded the train. The next day I had two red marks around my mouth like I sucked out of a glass all night.
I had a crush on him for more than a year, but that experience quickly destroyed any attraction towards him.
54. In It for the Food
I meet a guy online and when we went out, I could immediately tell that he was a dud, but I had no idea just how weird the night would get. First, he looks nothing like his profile—about 100 lbs. heavier, bad skin, and is just dressed really sloppily—but I told myself not to be shallow. Second, as we look at the menu, he refuses to eat anything except bread, meat, and cheese, and says he won’t eat any food if I order anything else. Third, he is the messiest eater I’ve seen in my life, but all this was nothing compared to the grand finale.
They clear our table for dessert and he then gets down on one knee and tries to give me a promise ring because he “felt a special bond with me and wanted to pledge his life to me” after having met online a few weeks before. Yeah, no thanks. Politely as I could, I declined, to which he started calling me expletives in the middle of the restaurant and then ugly crying and storming out.
So I had to pay for the terrible date HE asked ME on because I didn’t want to accept a pre-engagement ring.
55. Some People Are Lost Causes
I was at a party at a bar and I was hitting on this guy. I was really interested at the time, so I was giving it the full-court press. Like, I could not have been more clear. And he just was. Not. Getting. It. We ended up chatting about our families and he told me this story about how his parents met while serving in the forces.
It was like something something something his mother almost ended up getting court-martialed because his father didn’t realize she was completely in love with him, because his father was completely clueless. I slugged down the last of my drink, slammed the glass on the bar, looked him dead in the eye, and said, “Really? Is that a genetic trait?”
And…whoosh. He kept right on talking. I gave up after that.
56. Know Your Angles
I went on a date with a guy and we seemed to hit it off. It went so well that I immediately texted him “thank you for a great time, hope to do it again soon” when I got home from our very first date. His response? An, er, intimate pic. I wouldn’t have been so offended if it hadn’t been possibly the worst pic I’ve ever seen. Socks on.
Messy bedroom in the background featuring Naruto posters and a serious collection of Goosebumps books on the shelves and to top it all off…it was possibly one of the smallest I’ve seen. However, he seemed pretty pleased with what little he had to offer. He asked me (to paraphrase) if I liked what I saw and I responded awkwardly that I’m not a fan of clutter or mismatched socks.
He blocked my number after that so I guess that shows me?
57. We’re Going Where??
I met a girl at the local McDonald’s after school one day when I was 15. We talked and after realizing we got along, we exchanged numbers. She asked if I’d go out with her the next day. I thought she was gorgeous, and when she said I should dress up, I expected something special. Nope. So wrong. She took me to her grandma’s funeral.
58. Delayed Reaction
I was once dating a guy who was super bad at knowing when a girl was into him. I could tell he was into me but wasn’t getting my subtle hints, so I flat out told him, “I want to sleep with you.” He replied with “Thank you.” I clarified with “right now,” which didn’t result in him making a move for several more weeks.
59. Used Like A Saxophone
Got asked out by a girl I knew and was sort of interested in, but didn’t really know all that well. We went to an open-air jazz concert, not really my thing but sure. Once there she immediately was all over me (hugging, sitting on my lap etc.) Things were going great (or so I thought).
It was at that point when things started getting weird: several band members where giving us strange looks from stage, while playing their jazz music. One piano player was mouthing things in our direction, but I couldn’t make out what he wanted. People were rude to me for no reason whatsoever while getting drinks.
Long story short: my date knew just about all people there and wanted to get back publicly at her (very large) boyfriend for cheating on her. Don’t hate on me jazzpeople, I’m just an innocent sucka! Awkward ending: I met them both later that evening at the train station and she pretended not to see me.
60. Patrick Dateman
This was a third date with a guy from Hinge. Started off completely normal—went to a pub for a few drinks. Pub closes. Guy invites me back to his. We get back to his and have a few more drinks, he then asks if I’d like to smoke. Hadn’t smoked for a few years, but thought “hey it’ll be fine.” End up feeling very sick and unable to move.
Guy doesn’t have a bucket or bowl so brings over the entire kitchen bin and places it next to me. He then suggests we watch a movie. Guy puts on American Psycho, and I sit there for the next two hours paralyzed and paranoid, completely convinced he’s going to murder me. Also, he lived on a boat, which didn’t help.
61. All the Wrong Moves
I picked the guy up at his house. He didn’t introduce me to his sister and her boyfriend who we were talking with. We went to the movies, got to front of queue before he says, “I don’t have any money on me.” So, I paid. We went back to his house where I heard all about his ex and the amount of people he’d beaten up. He tried to get me to stay the night and refused to walk me out to my car. No second date for him.
62. There’s a Fire in My Heart
I was at a girl’s house and had to use the bathroom. Well, unfortunately, her family had candles in the windows for Christmas and the wire for the candle went right by the toilet. While I’m peeing, I sneezed, which messed up my aim. It set off a horrific chain of events. Of course, I end up hitting the wire and somehow starting an electrical fire.
Luckily, I was able to put it out, but of course I had to tell her what happened. I haven’t talked to her in a little over a year now.
63. Playing the Long Game
I went on a date with this girl from Tinder. She “super liked” me and messaged first, so I was really happy to have someone interested. I asked if she’d like to go for a walk some time and she said she’d love to. So we get to walking and like five minutes in, she asks if I have roommates. I said yes, I live with five people and tell her about a few of them.
“There’s Max, Matt, Mark…” “Wait, Mark Smith? I know him! What’s he been up to…”
So we start chatting about my roommate, and she knows a lot about him. His family, the sports he plays, his girlfriend. Every time I try to move the conversation somewhere else, she brings it back to Mark. She’s not even pretending to be into me anymore, she’s just fangirling out over my roommate. “I just love him, his hair is always so shiny and he smells so nice!”
She spends the full two hours talking about him and asking all sorts of questions. I didn’t really know what to do, so I just keep answering. When we get back to our cars, she shifts gears again. “Hey, so I had a really great time. Want to go back to your place to have some fun?” She’s really creeping me out at this point, so I tell her I have homework to do and maybe later.
I get back and tell Mark about the date. That’s when his face turns white as a sheet. He knows exactly who she is. He picks up his phone and immediately calls the police. They show up at the house, find the girl outside in the backyard, and arrest her for violating a restraining order or something. It turned out she was super unstable and had stalked my roommate since they went on one date almost a year prior.
She recognized me from photos she had of him and used me to find out where he lived.
64. Backseat Dater
She brought her best friend to a movie date. Date sat to my right. Best friend sat to my left. Awkward enough, but the friend’s bizarre actions made it even worse. He kept whispering, “C’mon man, make your move,” in my ear approximately every two minutes starting before the previews even wrapped up. Talk about a buzz-kill.
Worst of all, my date could hear, but seemed to find the whole thing to be perfectly normal. I did not make my move.
65. Can I Finish?
This guy was very attractive. He would occasionally come into my work. I never would have thought he would think I was attractive too. Well, he ended up asking me out. (Yay!) He arranged for dinner, but I would come to his place first. He immediately makes me a drink and also a shot of some type of liquor.
Not for us. For me only. He ends up trying to make out with me a short while later. And after a while of what I can only assume he thinks is that we’re playing a game of cat and mouse and him trying to shove my hand down his pants, I forcefully tell him to back off. He then asks if he “finish himself off.” He goes to the bathroom and has some, uh, alone time. We did not go on another date.
I flirted with a cute bank teller for weeks before working up the nerve to ask her out. I didn’t realize she was super religious, invited her to a Mexican restaurant, and ordered two margaritas. When she told me that she doesn’t drink, I said, “That’s ok. These are uhh… these are both for me!” She told me I wasn’t Christian enough for her and I agreed. And there I sat, drinking two margaritas alone.
67. Parents and Video Games
I met a guy from OKCupid. The first time we met up in a public place and just had a casual chat. It wasn’t a horrible date, but it wasn’t very memorable either. I decided to give him another try because it could have just been nerves. The second date he invited me over to his place… I knew he lived with his parents, but I kind of assumed they’d be away. Nope. I was so wrong.
They were definitely home and seemed to very much want to be part of our date. They kept coming into the lounge room and giving us iced tea and chips whilst he played XBox in his track pants (no shirt) and I sat there awkwardly watching. He didn’t really speak much to me. It was 11 pm, and he was in his 30s.
68. The Old College Try
When I was about 35, I lived in a beach town near a university. My neighbors were all college kids. Next door were two college girls. One was always flirting with me. One hot summer day, she turned up at my door in nothing but a long T-shirt. She asked if she could hang out in the A/C. I said sure, and she came over to the sofa I was sitting on and laid with her back to my chest and asked if we could snuggle.
I was okay with that. She then asked me to rub her belly, which I did. As you can imagine, after about an hour, I was getting a little worked up and touched her breast while rubbing her belly. She jumped up and stormed out. I was like…uh? She later said she didn’t see me like that. I asked her why she’d show up almost naked, lay between my legs like couples do, and ask me to rub her belly and then get peeved when I try to progress things.
She said she looks at me like a big brother. I was like, what the heck is your family like?
69. Inappropriate Dad Jokes
This girl’s father had just recently passed on, so I invited her over to make her dinner and console her. We make dinner and we are talking about stand-up comedians and she tells me she’s never seen Louis C.K. so I say we need to watch one of his standups. Well I turn on one randomly and the first 25 minutes are dead dad/parent jokes.
70. The Zombie Apocalypse
After crushing on my cute co-worker for months, we finally got drinks and things escalated. Fast forward to later that night. We’re both asleep at her place. I hadn’t been sleeping well for the past week and when I’m sleep deprived, I tend to have weird dreams, sleep walk, and sleep talk. So I had this nightmare where a zombie attacks me and I have to fight for my life.
In real life, it was ten times worse. What had actually happened outside of the dream was my date tried to cuddle me and I responded by freaking out and literally throwing her out of the bed. She screamed and that partially woke me up but I’m still mostly in the dream. I just start yelling things. “Who are you? Where’s your clothes? Get away from me!”
I woke up fully as she was storming out of the room. She thought I was trying to be a jerk, I suppose. I was absolutely mortified. No joke, I felt awful. I thought I blew it. Once I went out and explained what happened, she thought it was hilarious and came back.
71. Can You Hear Me Now?
It was a blind date. Her mom worked with my mom. I saw a picture of her, she’s very pretty. I called her and set up a date. The phone call left me feeling like she might not be into it. This continued after I picked her up. Most things I said got an unenthusiastic response of a drawn out, “Yeahh.” I couldn’t figure it out.
Want to do this? Want to go here? Want to go there? “Yeahh.” When I learned the truth, I nearly passed out with embarrassment. It turns out that she was mostly deaf. Even worse, nobody (including my own mother) told me. I ruined it by not knowing she had a hearing problem. I still feel bad about it. I could have done better if I had known.
72. Flirting With Rage
Finally get to share this story! A couple of years ago I dabbled a bit with Tinder. Met one guy who was super cute, traveled a lot, and seemed interesting. I suppose “interesting” was one word I could use to describe him. We start the date by getting lunch and a few beers at my favorite spot in town. We were chatting away and the topic of daydreaming came up. I asked him what he daydreamed about.
His eyes then get a bit dark and his voice gets low as he says, “When I daydream, I imagine the light leaving my enemy’s eyes.” By this point I was a few beers in and didn’t know what to say. I respond with, “Oh…so uh, how do you do it?” He looks away, ponders for a second and says, “Harpoon.” The rest of the date was spent with him talking to me about his extensive anger issues and how he still lives and sleeps with his ex. Heck, he had just slept with her before he came to meet up with me. That was when I decided to stop using Tinder.
73. Destiny, Tears, and Soiled Pants
Okay. So, I went on one date with a guy that I met on Facebook (mutual friends). Now that I think back on it, he may have had some serious mental problems. He was really sweet and handsome, but towards the end of the date he said something like, “I really think this is destiny like we are meant to be.” And I just laughed along with it and said, “cool,” or something.
He then said, “I had a dream we got married and I think it’s going to come true.” And then looked at me like it was the most romantic thing a guy could say. After a long silence, I burst out laughing and see that he’s visibly upset. He then begins to shake and start sobbing. I say something along the lines of “oh my god, I’m so sorry. I just like to take things slow.”
“You caught me off guard with that comment!” He shouted back through hot tears, “You caught my heart off guard!” I sat with him for a while longer with the only sound between us being his quiet sobbing. Oh, but it gets worse. He suddenly stops and I smell the most potent, disgusting smell I think I’ve ever smelled. He looks at me accusingly and says through his tears, “I just pooped myself.”
After stifling a laugh, trying to comfort him, and sitting next to a wailing, soiled 26-year-old man for a few more minutes, the smell became too much so I mumbled an excuse and left him there. In a pile of his own poop and tears. A few days later, I received a Facebook message from him apologizing for his “little accident” and informing me that I “still drive him crazy.” I blocked him.
74. Let’s Get You Into Some Wet Clothes
It was our third date and I’d driven my project car because I’d just gotten it on the road. It started raining right before dinner. By the time we came out of the restaurant, it was a pretty torrential downpour. We hopped in the car and started driving to the bowling alley. Well, apparently the seal around the T-tops leaked and a bunch of water had pooled in the frame underneath.
The first corner we went around, it all dumped out on her. She was soaked. Whoops. She said it was alright, but I knew it wasn’t.
75. Taco ‘Bout Embarrassing
I was eating tacos in a mall food court. He walked by me and I thought he was cute, but as I was about to say something, I inhaled wrong and started choking on my taco. He looked at me weird and quickly walked away. My friend went and got his number for me. This was seven years ago. He told me he thought I was laughing at him. Thanks, Taco Bell!
76. When You Gotta Go, You Gotta Go. Hard.
20-year-old me went out to dinner to meet her family for the first time. Got dressed up in nice khakis and a sweater. In the middle I farted but ended up pooping my pants with liquid death. There was no hiding the smell, as well as the HUGE FREAKING STAIN ON MY PANTS. It was awkward for all those involved.
77. 50 Shades of No Way
On two separate occasions, the first time I’ve gone home to a guy’s place, he’s had a variety of intimate toys laid out on the bed. And I’m not talking about regular stuff, either. I’m talking full-on specialist stuff. There were more than ten implements, bundles of rope, and fine leather goods. Everything was just laid out there, as if he’s expecting me to be like a kid in a toy store with all the possibilities the night has opened up.
I mean, I don’t mind getting wild, and if I’m going home with you it’s a pretty safe bet that you’re getting some. But for God’s sake, man, you can’t just put that stuff out there as-is. You’ve got to give a girl some warning. You can’t just assume.
78. How NOT To Act On A First Date
I met this guy because he was staying with one of my friends. His family had recently kicked him out. He was cute, and I thought that a date would raise his spirits. However, the entire date he talked about his favorite serial killers, which serial killers he thought were attractive, the mistakes the serial killers did that got them caught, and how he would kill someone if he just had enough courage to.
He kept on bragging that he knew the perfect way to kill and get away with it. Half way through the date, I got sick. I was glad to call it off at that point. After the date, he told everyone that would listen terrible things about me that were not even true. My friend kicked him out soon after, and I do not know where he is now.
79. Tickle Me Taekwondo
I kicked my date in the face because she was tickling my feet and I couldn’t control my movements. Knocked out her tooth. I felt horrible and paid a pretty penny for it to be replaced. On the upside, she never tried that with me again. This was 4 years ago and we’ve been happily married for a just under a year now.
80. I Think This Counts as an Emergency Worth Escaping
I was bartending in NY and watched this couple who had met on Tinder have their first date sitting at my bar. The girl was a complete maniac. Kept bringing up the fact that the dude she was with could be a psychopath and could murder her (he had given no indication of this) and went on Tinder while he was still sitting beside her at the bar.
She kept telling him he was lucky that she agreed to meet him at all, and she didn’t think he’d be this boring. She ordered about 5 or 6 LITs and several shots, he literally just had two beers. She made him pay for everything. My favorite part was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. Straight up thought he had disappeared out of the bar.
81. Bad Drunken Decision
I was out one night, and had beyond enough to drink. I went to a cafe next door to the bar, grabbed some food and hung out for a while. This guy walks in. He’s kind of cute, so we start talking and I invited him to share my sweet potato fries with me. One thing led to another, we went outside, made out for a while and then we took a taxi back to my place.
Everything seemed fine until I tried to drop him off the next morning. I asked him where he lived, and he kind of avoided the question, just giving me directions. To the local homeless shelter. He was homeless. And he admitted he was homeless because he just got out of jail. For assaulting a woman. I had given him my number before any of that came out, and he called constantly. After a day, I had to block all unknown numbers on my phone, because (being homeless and all) he called from a different number every time. It was miserable, and it took nearly a month for the messages to stop (thank god for visual voicemail).
82. This Can’t Go Wrong in Any Way…
This was his pick-up line: “I’m a recovering gambling addict, want to go to Vegas with me?”
83. Try Google Translate Next Time
Teenage me was hitting it off with this smoking hot French girl when out of the blue we stumbled into a friend of mine. The dude became a third wheel but actually managed to completely steal the girl away from me. They started kissing in front of me after roughly 45 minutes. But that’s not even the worst part. Dude didn’t speak a word of French, and they needed/requested me to tag along to translate for each other. Gonna pass on that opportunity, thanks.
84. Dinner With a No Hit Wonder
I work at a dinner theater. We usually do proposals where we set up a “random draw” where the “winner” comes up on the stage to win their prize and are then surprised by their partner, who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm. This one guy wanted to take it further, and requested to perform a song—he brought his own music and everything. We’re pretty easy-going at this job, so we agree to let him do it. That was the beginning of the nightmare.
We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently, this guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy that seemed to focus on how he was sorry for cheating on this woman with her sister, and at the end of it, he gets down on one knee and proposes.
Usually this gets a round of applause, encouraging the person to say yes, but not after that train wreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says, “No, what’s wrong with you?” She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is, “Well, that’s that.” The guy ended up staying for the rest of the show and had many more drinks. That was years ago, and it still remains one of the cringiest things I’ve ever seen.
85. What’s Your Number?
Waiter here. I saw an obvious first date where the lady was grilling the guy on how much money he makes. He didn’t really want to answer. It was awkward serving steak and salad during an interrogation.
86. Think of This as a Learning Experience
I asked a girl in my class out on a date a few years ago, we had all the details set in stone, and I showed up to find out she invited the 30 other people from the class. I had to sit through an hour and a half of the “class lunch,” which she gave me credit for organizing, and pretend that I didn’t think it was gonna be a date the whole time. Ouch.
87. Parental Pick Up
He called 20 minutes before he was supposed to pick me up. Told me he’d be a couple hours late because he wanted to play basketball. I should have known this would be a mess but I was young and naive. By the time he was supposed to get me rolled around, he was still a no show. Twenty minutes later a car pulls up and his mom gets out (keep in mind we’re freshmen in college).
He sent his parents to come get me. I had a 20-minute drive to his house in the car, alone with his parents. When I got to the house, things did not get any better. He proceeded to talk about the girl he was in love with for the rest of the date and ended it with an awkward hug stating that it wouldn’t work because we lived too far away.
88. What Did You Expect From A Movie Titled “Happy Feet”
This was in high school, some girl from our rival school and I met, hit it off. She really wanted to see Happy Feet, the dancing penguin movie. Decide to take her, I like penguins anyways. I swear about half way through the movie she leans over to me and says, “Oh I get it, they’re dancing!” I thought she was trying to be cute, but she was serious. This movie was her idea, I figured she knew. The penguins were dancing for at least an hour before she said this to me. We lasted another week.
89. Twilight Times
I met a girl in a club and we ended up going back to her place. When we got into her room it was like a normal student room, posters on the wall etc, typical girl stuff, y’know? Twilight poster, calendar of a boy band, some frilly stuff… all that. Anyway, we’re about to get down to business when she whispers into my ear in the sexiest way possible, “Bite me like Edward.” I had my clothes on and was out of the door faster than you could even imagine.
90. Love Slap
I took a girl who I really liked on a first date to the movies. About halfway into the show, I noticed she had a piece of hair hanging down in front of her face. Me, being the gentlemen that I am, saw this as an opportunity to be cute and go in for the kiss.
Screw me, was I ever wrong. I thought to myself, “I’ll reach over and move her hair out of her face which will then lead into the kiss and it’ll be cute.” So, I lean in and reach over to move the hair from her face and make my ‘smooth move’….and as my hand got to within 6 inches of the target zone she reaches up and moves the freaking hair herself!!
At this point, I’m already 90% of the way there, with my hand in front of her face, blocking her view of the movie. My cute plan dissolved and there was no purpose for my hand anymore, yet it was still on a collision course with her face and for some reason, I couldn’t stop it. I reached over and wiped her forehead, taking whatever makeup that was there with me. Leaving her with an obvious stripe on her forehead that was most noticeable during the brighter scenes.
She looked at me horrified. She didn’t even have it in her to ask me what the heck I was thinking because she was so shocked. My entire world turned to flames and the room got considerably hotter. And I didn’t get my cute first kiss. In fact, I got a deleted number…
91. It’s Not Crazy if it Works
I got super drunk at a New Year’s Eve party and ended up sleeping at a girl’s apartment that night. After sobering up, I made a decision I still can’t quite understand to this day: I decided to get naked and crawl into her bathtub. I passed out, but woke up with a blanket on me, and a pillow under my head…She sent me a message asking if I was ok.
I asked her out for coffee. We’ve been dating for a year.
92. Dark Date
I met a guy at the skate park when I was 14. He asked if I’d go out with him the next day. I thought he was gorgeous, and when he said I should dress up I expected something special. The next day I showed up, and I couldn’t believe my eyes. He took me to his little sister’s funeral.
93. The Rank Smell of Rejection
A guy got stood up. He then drank a magnum bottle of red wine (8 glasses of wine) and ate three apps out of depression. His date called him, and he started cussing her out. He asked for more wine and then I had to cut him off. So he got up and tried to run out of the restaurant with a bottle he grabbed from a rack. An off-duty cop tackled him in the lobby, and then he pooped his pants in front of everyone waiting for a table. He lied there screaming with the guy holding him down until the cops arrived and arrested him. This is my fondest memory of being a bartender at Olive Garden.
94. When He Gets Rejected, He Gets Salty
When a coworker asked me out, I said no and went on with my day. Then I made a truly chilling discovery. The guy who asked me on a date had closed the restaurant the night before and knew I was opening the next morning. He’d taken salt and poured it all over the office desk. It was shaped it to say “DIE,” followed by my full name.
95. Ice Cold
It was a blind date. I got there first and sat down outside. He ended up calling me on his way and I told him where I was sitting. He was still on the phone as he came up, but he took one look at me and suddenly hung up the phone and walked back to his car. I know I should have understood the situation immediately, but I was in total denial. I tried to call him back, thinking something must have happened, and he didn’t answer. No more answers to calls or texts afterward. That one really hurt.