When a first date goes well, you feel like you’re walking on air. Unfortunately for these people, that …didn’t happen. These first date stories are not about those match made in heaven moments. Instead, they’re full of awkward moments, embarrassing encounters, and just plain creepy people. Strap in: These are the worst first dates of all time.
1. Pick A Good One
A guy told me he really liked to snuggle with his mom. He was almost 30 years old.
2. Meal Ticket
This is back in the prehistoric era known as the mid-1990s when I was 19. I met a cute redhead at a party and instantly asked her out. So we go out to dinner, her pick, and she chooses Marie Callendars (I’m like WTF? But hey supercheap date). The entire time we are there nothing but silence though she orders a huge meal and I’m thinking she has the metabolism of a race horse to be that skinny and eat so much food.
Our meal shows up and she goes down on the pot roast like a savage and in between bites she regales me with how she lost her job and is living in a rundown house that has a leaky roof, the powers been turned off, oh and she and her LESBIAN girlfriend have been starving (her emphasis not mine).
With that revelation, I’m struck speechless and don’t really know what to do. She has her leftovers boxed up (plenty for her girlfriend) and dashes before the bill is even presented to me. At least we were too young to drink. Some friends confirmed her story and I was the butt of some jokes for awhile. Even at the time I found the whole thing surreal and hilarious. At least shortly afterward.
3. A Horrifying Experience
I used to be a waiter at Olive Garden. One time, a couple was there on a blind date. At one point, the dude went to the bathroom and didn’t come out. Thirty minutes later, an ambulance shows up. He had apparently taken something in the bathroom, overdosed, and passed. The girl was traumatized. Yeah, we all went home early that day.
4. The Zombie Apocalypse
I’d been interested in my cute co-worker for a while but we were just friends and that was fine. Still, we hung out a lot and eventually one night we got drinks after work and things escalated. Fast forward to later that night. We’re both asleep at her place. Now, I hadn’t been sleeping well all that week partially because of her dragging me out with her.
And when I’m sleep deprived, I have very strange dreams and am prone to sleep walking/talking. In my dream I’m walking done this tunnel, like a metro tunnel. I see this girl on the ground crying. She’s got no clothes. I ask her what’s wrong and she lunges at me. She was a zombie or something. She wraps her corpse arms around me and I throw her off and start yelling.
That’s what I was seeing. I was fighting for my life. In real life, it was ten times worse. What had actually happened outside of the dream was she tried to cuddle with 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.
She asks me what’s wrong and 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.
5. Empty Your Pockets
The most awkward first date? When his wedding ring fell out of his pocket midway through dinner.
6. Law And Order
I once went on a date with a law enforcement officer. My mom set it up but it seemed like he was an alright guy, so I agreed. We went out to lunch. He proceeded to tell me about his kids and talk about his hobbies. Afterward, he offered to show me around the town since I had just moved here. Turns out he was actually driving over to his ex-wife’s house to introduce me to his kids.
7. Accidents Happen
Bartender here! So, I used to work at a place that was well known for our wings. I witnessed what was obviously a Tinder date go belly up. I greeted everyone and got the ball rolling. After a few drinks, I could tell they were very obviously into each other. I was happy that they were happy. But, as we all know, stuff happens. And it was about to happen tonight.
I make a pass back their way, and ask if they want to do another round. They both eagerly agree, and while I’m making their drinks I hear the guy say, “What do I have to do for a kiss?” Aww, cute. The girl thinks for a second, and then says, “eat a spoonful of their spiciest sauce.” When I come back with their drinks, he asks me for a side of our hottest sauce.
I tried so hard to talk him out of it. When that didn’t work, I did the only other thing I could do and grabbed my cook to witness this idiotic move. The cook brings out the sauce and gives it to the guy. We warn him one more time that this is an AWFUL idea. Guy shrugs us off, and tips back the little ramekin. Things were fine, at first.
Then tears were streaming down his face, I got him some milk, and I thought we were over the worst of it after five minutes pass. I was wrong. Dude kicks off his shoes, stands up, and runs to the back of the bar. As he is running, poo starts escaping his pant leg and leaves a trail all the way to the bathroom. I couldn’t believe it.
He refused to come out until his date left. He never got the kiss! I just cannot believe this guy had the forethought to take off his shoes before he publicly pooped his pants. To be fair, they were really nice kicks.
8. Save It For Later
This happened at my former restaurant. There was a reservation for 6:00, a young guy comes in a few minutes early, tells me he’s kind of nervous because it’s a first date and he hasn’t had many before, blah blah blah, kind of sweet really. Anyway, the girl arrives about half-an-hour late and proceeds to get very, very drunk.
About mid-way through the meal, she answers her phone, takes the call, and starts talking about her date, in front of her date, saying stuff like, “Well, he’s not usually my type, I don’t exactly like him, but I felt like why not,” right in front of him. The young man looks so discouraged, walks up to me, pays his bill, and leaves. Watching that one hurt.
9. We’re Going Where??
I didn’t mess up the date. The date was just messed up. I met a girl at the local McDonald’s after school one day when I was 15. We talked and then 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. She took me to her grandma’s funeral.
10. Pick A Partner
My prom date was pretty bad. It was a double date with some girl I’d never met. Turned out we had both just been dumped. I tried to make conversation about random topics, but she just wanted to talk about how annoying her ex was. We get to prom and it turns out that her ex, who I’d also never met, was there—but that’s not the worst part.
He was there as my ex’s date. My date then spent the rest of the evening trying to get her ex to come back to her.
11. Love Is Blind
My aunty set up a date for me. I am half Asian and half European, and my family wanted me to date and probably marry this girl because she comes from a rich family. So, we met at a restaurant and she brought her brother. He brought his girlfriend. I went there with a cousin and he thought the whole thing was hilarious.
We introduce each other but its loud and they mumble so I don’t understand their names. I decide not to ask them all for their names. I didn’t want to be rude. So, I talk to this girl and she is educated and good looking as well. I start to think: Hey, this wasn’t a bad idea. I actually like her and we seem to be on the same wave length.
I start to flirt with her and she seems to like it. Then suddenly the brother says something and they just leave without saying anything. I am totally confused. Then I learned the awful truth. It turns out I was flirting with the brother’s girlfriend the whole time and I never even looked at the girl I was supposed to date except when we introduced each other.
12. Nothing Can Come Between Us, Except…
I worked at an upscale seafood restaurant for about a year. One particular woman would bring in a different date each week. Every single time she was there, she would start the date by erecting some kind of barrier on the table between herself and her guest. I’m talking salt and pepper shakers, menus, dishes, drinks, etc.
Whatever she could get her hands on at the table, she would use to construct this physical barrier with. She would then carry on with the date and with her conversation as if things were completely normal. The confusion and distress on the faces of the men she would bring in was always my favorite part of Saturday night. Still have no idea what was going on.
13. Want To Help With The Groceries
I had just moved to London, and met this guy on a dating website, he was generally not my type. Still, I was fresh out of a long-term damaging relationship and trying to meet new people yada, yada. Fast forward to the date, and he takes a call from a girl and he 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 already ringing.
He hangs up the phone and says “that was my fiance, but not a real one, just one I’m with for her visa.” At this point I’m already thinking “oh jeez.” He continued on with his excuse: “She also lives with me” (in his two bedroom apartment with this other roommate—cosy). “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?”
14. Memory Loss
This is not the worst thing that ever happened, but it’s still kind of funny. I once took this girl out for a first date. We went to a play and then out for drinks at a bar afterward. While we were enjoying our drinks, she suddenly stopped me in the middle of our conversation and said: “You don’t remember, do you?” Turns out we had slept together like five years earlier…
15. Too Kinky Too Soon
On two separate occasions, the first time I’ve gone home to a guy’s place, I’ve seen a horrific sight. Both times, 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.
16. 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.
17. Photo Finish
I was at my new boyfriend’s house for the first time when I noticed a certain photo on the wall. I said “What? We have that same photo at home! Why do you have a photo of my great-grandmother on your wall?” Looking at me confused, he said “Because she is my great-grandmother!” I will never forget the shudder I felt when we realized what this meant…
18. A Lively Woman
A friend and I meet up at a chain restaurant for a meal and a catch-up, in the booth across from us are a guy and a girl in their twenties, very obviously on a date. Things seem to be going moderately well, just kind of let them do their thing in the background as my friend and I chat about life and stuff. Then, the guy stands up halfway through the girl’s sentence, cutting her off.
It’s quite a violent movement, so it draws the attention of most tables nearby. The guy then says, in a way that makes me think he has rehearsed: “I’m sorry Jen. I just wanted to give women one more chance, but I can’t do it, you’re lively, but women just aren’t doing it for me.” The guy throws some money on the table and walks out. She kind of sits there with everyone looking at her, going redder and redder.
The lovely waitress swoops in, and saves the day for her, but wow. Never seen anything that completely insane before or since—at least just wait for the date to be over and politely decline a second.
19. Trust, But Don’t Verify!
I once witnessed a very awkward first date in a restaurant. In short, the girl stated that she was allergic to pineapple. The guy basically responded by implying that he didn’t believe her. Later in the evening, when she had left the table to take a phone call, he secretly scraped some pineapple glaze off of his dessert and onto her spoon.
She came back and started eating without noticing too much at first, but then quickly had a severe allergic reaction. The guy freaked out and tried to run away, but he got stopped by a customer from another table who was suspicious of him. The manager administered the girl’s EpiPen and called an ambulance, as well as the authorities. It was an absolute circus.
20. Better Late Than Never?
A while after my parents split, my mom joined a dating site. She met up halfway with a guy who lived pretty far away (at least two hours) and he was late. 45 minutes later, he stumbles into the restaurant completely hammered. He starts towards my mom’s table, trips, and smacks his head on the corner of the table she was sitting at.
He then fell unconscious and began bleeding profusely from the forehead. Literally everyone in the restaurant is frozen and in awe staring at him, passed out, bloody, and drunk. For whatever RIDICULOUS reason, instead of just calling an ambulance and leaving, my mom decides to drive the unconscious man to the hospital and spends all night there to talk to him when he wakes up.
She stayed essentially just to say there won’t be a second date and officially reject him in person. I can’t remember if she drove him home or not but it’s a possibility. She’s insane.
21. 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.
22. No Clowning Around
I met this girl on Tinder. She seemed cute enough and the conversation wasn’t as stale as the other matches I had, so we decided to meet up over coffee. On the big day, I go to pick her up at her house, knock on the door and she opens. She was, to say the least… not at all like her pictures. She was much bigger, and her face didn’t even look the same.
I’m already disappointed but I’m already here and it would be rude to back out now. So she gets in my car and we start driving to Starbucks. On the way there, we talked in the car for a bit and it becomes apparent to me that she is an “XD RAWR so rand0m” type girl. But again…I’m already here… We get to Starbucks and she gets me to order for her because “I just can’t handle that right now.” Ok …
We sit down and I’m already counting the minutes until it wouldn’t be rude to call it a night. We start talking, well, I start talking. The most I can get out of her is yes, no, or a slight laugh if I tell a joke. From talking to her like this, I find out she’s actually only 18, her profile said 21 (my age). Not a huge deal but I wouldn’t have gone out with her had I known that before.
Eventually I ask her what she does. IMMEDIATELY, in one breath she screams out “I’MSOGLADYOUASKED I’M A PROFESSIONAL CLOWN WANNAHEARMYCLOWNLAUGH HHOOOOOOONNKKKK HAHAHAHHAHAHAHHAHA.”
I am mortified, the entire coffee shop turns to look, and she is oblivious to it. Suddenly she is no longer this weird shy girl. She starts telling me all these stories about her clown adventures. This goes on for probably 8 minutes. Everyone around is snickering and obviously listening in on it (not that they had much choice). Oh and it gets so much worse.
She then tells me LOUDLY how her boss and one of her coworkers propositioned her for a three-way. She goes on to say, “Yeah I thought about it, but he’s 40 and I was 17 at the time so I decided not to. Plus, we were doing a child’s birthday party at the time, so it might not have been appropriate.” I wanted to sink into the earth and dissolve.
As soon as she says that, a girl in the corner of the coffee shop lets out a stifled laugh. My date notices and goes beet red. I suggest maybe we should call it a night because I had an exam the next day. She saw through my lie but went with it. A few minutes later I realize tomorrow was Sunday. I drive her home; awkward silence follows for the 15-minute drive.
We arrive, I stay silent and don’t get out of the car. She sits there for a bit not saying anything. I go, “soooo…” What follows next is 100% true. She said this. I can’t ever forget it. She blurts out “Wanna come inside and do it while my cats watch?” Yeah…she said that. I stay silent for about 10 seconds because I don’t know what to say.
I eventually say “I uhh, don’t have any protection sorry.” She gets the message and leaves. I hightail it out of there and never spoke to her again.
23. This Can’t Go Wrong in Any Way…
“I’m a recovering gambling addict, want to go to Vegas with me?”
24. Pop Goes the Weasel
I once went out on an eHarmony date to a high-end bar with a huge beer selection. The girl shows up and she doesn’t look anything like her photos. She proceeded to drink seven Miller Lights, then proceeded to tell me some very weird things. For example, she told me that the reason she didn’t want to be single anymore was that she missed having someone to pop the zits on her back.
At the end of the date, she asked if I wanted some gum. I politely declined. She went in for a kiss and I turned it into a hug instead. Needless to say, this was the first and last date that we had together.
25. Red Flags
So I met this girl on Tinder. She seemed nice enough at the time and I was sorta new to this whole Tinder thing so I must admit the red flags slipped right past me. She rocked up half drunk in a torn dress. Now I’m not one to judge people’s lifestyles and I was starving, so for some reason I decided to press on with the date.
Bad decision. I spent the next three hours listening to her moan about her current boyfriend and how he was such a controlling guy because he wouldn’t let her go out on one-on-one “catch ups” with guys at bars. When I finally came to my senses and told her that I didn’t particularly want to be on a date with a girl who was seeing someone, she threw her drink at me and accused me of assaulting her.
Thankfully, the bartender had been watching the entire series of events and took my side on it. She got thrown out, and I didn’t go on another Tinder date for the next few months.
26. 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.
27. The Great Escape
When I was 22 years old, I worked as a busboy at a 200-seat restaurant that was part of a sporting club. I’d been there for long enough to have a feel for the personalities of the customers. On this one particular night, one of my tables was a first date. The girl was lovely, all smiles and very pleasant. The guy was sort of normal, but seemed a bit quiet.
When I was at the table, the guy gave off some fairly clear signals that he would prefer to be left alone. That’s okay, some customers prefer minimal service. What I did notice, though, was that he was talking to the girl quietly, but forcefully, and almost non-stop. Sometimes, he was gripping her arm firmly, in a way that suggested that she wouldn’t be able to pull away easily.
I couldn’t hear a word that was said, but the lady was looking more and more terrified all the time. Like, nearly about to wet herself terrified. It was a complete change from her pleasant nature that she had displayed when they first walked in. I told the waitress on the adjacent section that I wasn’t sure about what was going on.
I asked if she wouldn’t mind checking on the table to let me know her thoughts. So the waitress went to the table, said a few quick words, and came back to me. Out of earshot, she said, “Yeah, I think we have to get her out of there.” It was clear that this man was threatening to harm her when they left the restaurant.
We let the manager know what was going on. The guy had booked his table, which was good. We had his name. Outside at the taxi rank, by some miracle, there was a female cabbie in the line. I ignored the protests of the other drivers. I hopped in, told the cabbie the situation, and offered her $20 to wait around the back of the restaurant.
I said, “Please don’t wait for a destination, just drive, something’s really wrong with her date.” The cabbie said she didn’t need the $20. So then we put our plan in motion. We had the front desk call the man over to the phone, claiming he had an “urgent call.” This would delay him. But there was a snag: He was trying to figure out what the “call” was.
So then my coworkers announced that he had just won a free meat tray in a raffle. Luckily, prizes like that actually were raffled off at various intervals throughout the night, so the excuse was totally believable. “Just wait here while we fetch it for you!!” As soon as the creepy guy was out of sight of the table, I asked his date if she needed to get out of here.
She just trembled and nodded. Figuring that she probably wasn’t in the mood to trust a male at that point, my waitress friend escorted her through the kitchen and out to the waiting cab, where she slipped away as quickly as you please. The guy eventually came back to an empty table, and the staff just acted oblivious when he asked where his lady friend had gone.
We didn’t get much of the story, other than the fact that the lady had been set up on a blind date by a mutual friend who told her that this guy was nice.
28. The More You Know!
I met this girl and hit it off pretty well with her. I hang out at her place one night, get home, and decide to look her up and add her on Facebook. As soon as I look her up, I discover that she has an eight-month-old kid and a husband in Iraq. Both details she decided to leave out. When I confronted her about it, her response was unbelievable. She just said, “Well, I didn’t think that would bother you.”
29. Fool Me Once, But Not Twice In One Night
Met a girl online, decided that we should meet for a date (I’m female BTW—this sort of matters). I arrived in a strange town that I didn’t know so I relied on her to show me around. She took me to a youth LGBT group, I thought we were staying, didn’t mind—it’s a bit odd but I was newly “out.”
Turns out it was just a chance for this girl to show off that she did, in fact, have a date (they didn’t believe her apparently) and I existed. It was really awkward. When the youth group leader came in, she stood up, grabbed my hand and said “later” and we walked out. Went to a bar for a drink, and then on for some food. It wasn’t going well, she was very odd, but I was new to all this, and in a town I didn’t know.
Once we’d eaten she said, “oOh I just need to see a mate who’s staying at xyz hotel”—fine, went to see this friend. Oh no. She’d booked a hotel room for us for the night! Yeah—I left pretty quickly after that. I may have been inexperienced, but I wasn’t about to be tricked into a night in a rough hotel with an odd little lesbian. No thank you.
30. 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 he is 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.
31. Try Google Translate Next Time
I was hitting it off with this incredibly hot French-speaking girl (the type they employ in nightclubs to dance in the cage or on the luminescent block), when out of the blue we stumbled into a friend of mine. The dude became somewhat a third wheel but actually managed to completely romance the girl away from me. They started kissing in front of me after roughly 45 minutes.
Here’s the bad part: dude didn’t speak a word of French, and they needed/requested me to tag along to translate for each other… Needless to say it didn’t take long for me to find a way out and spend the rest of my summer angry, humiliated, and depressed. Never saw or talked to either of them since.
32. Just… No
Tinder matched with a guy who was half an hour late for the date. The first thing he said to me was “You’re too tall, you’re taller than me.” I’m 5’5″, was wearing flats—nowhere on his profile was his height listed, never mentioned anything about it. He said he’d buy me a drink for being late, so I figured I’d get a beer out of it.
We chatted for a bit about our jobs and school and whatever. I check the time, and realize I have to catch my bus back home—I lived in the suburbs with my parents at this point. He says “Okay, I’m coming with you.” “Uh, no.” ”Well, I guess you can come back to my place. My roommate is there though.” ”I’m not coming home with you, I made that clear long before we even met up.” “I bought you a drink! You owe me!” “What the heck? I owe you nothing.”
He puts on this super angry face and starts negging me. ”You’re not even that hot.” “I am not going to sleep with you. I’m going home.” He just stalks off in the opposite direction. I get a message on Tinder later. ”This isn’t going to work out.” Uh. Obviously. Lol. Came across this dude on Bumble later. His profile pic was a pic of his abs; the secondary pic was him sending “sexy” texts with a girl. Lmao. Good luck pal. Good luck.
33. Don’t Assume
I accidentally went on a date with a guy in my apartment block, only to see his disappointed face when my girlfriend called me on the way home. I realized he’d assumed I was gay and that I’d assumed he was just a friendly guy wanted to hang out.
34. 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 answer was utterly disturbing.
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.
35. Dating To Steal
I went for a meal with this girl I met through a dating app and it was going really well. We started talking about movies and then we decided to go to the movies to go watch Inception. She said there was a cinema nearby but I didn’t know the area at all, so I used the GPS on my phone and she held it and directed me. Once we got there we started walking inside and I realized I didn’t have my phone in my pocket.
I said I must have left it in the car and started to walk back to get it. She was trying to get me to leave it and saying we would miss the film but the phone was only about a week old so I was really paranoid about it. We checked the car for about ten minutes but we couldn’t find it. I asked her to check her jacket and her bag but she said it wasn’t there.
A couple parked next to us so I asked them to ring my number because I couldn’t find it. It started to ring and it was obviously coming from my dates handbag. She took it out and said she must have missed it. I thanked the couple and locked my car and as I turned back around she was walking the other way. I ran to catch up and asked what was going on but she was very dismissive and was barely talking. That’s when I realized it wasn’t an accident and just left her to walk home alone.
36. If It Quacks Like a Duck…
I once went out with a guy on a simple park date. Got a snack—ya know, normal stuff. Then, out of nowhere, he pulled a pistol out, shot a duck two feet away from us, and asked me if I wanted to take it home. Oh boy…
37. You Could Be My Other Guy
I’m a dude. I was about 16 at the time. My female cousin tried to hook me up with her “nice friend” whom I had shown interest in after meeting her at a family gathering. We text and talk on the phone for a couple weeks. Later we agreed to meet at the mall.
We get to the mall and the girl shows up with another guy, who is her boyfriend. Yes, she introduces him as such and all that. Apparently, he was her ride to the mall. My cousin didn’t think this was odd. I was highly annoyed the whole time because the girl is really fine. We walk around the mall, the girl, my cousin, and myself. The boyfriend waits in the car.
The girl tries to get me to buy her stuff in the mall, I lie and say, “Oh, I don’t have it like that right now.” She tries to hold my hand, asks me to get her something at the food court, the latter I give in and do. I tell my cousin I’m ready to leave. And the girl goes, “You’re cute. And sweet. You should totally be my guy.” I was dumbfounded.
I asked, “Don’t you already have a bf?” Her reply was insane: “I could have two! Besides, he’s just my brother. I don’t have to commit to him.” My jaw drops, and I just tell her no thank you, and leave quickly. My cousin asks what’s wrong, STILL no seeing the problem with her friend’s relationship status. I’m still weirded out by that to this day.
38. 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.
39. 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. In the single most stupid idea of my life, I thought, “I can fix this!” and put my hand inside the nozzle of the dryer. WHY!? WHY THE HECK!? 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.”
40. Two’s Company, Four’s a Crowd
I asked a girl on a date. She said sure. We agreed on the details, I’ll pick her up at 4 pm, then we can do go-karts at the local speedway. Unbeknownst to me, she invited 2 of her friends. Since I was a spineless 19-year-old at the time, I couldn’t assert myself to tell her friend not to smoke in my car, and also that I don’t want to pay for their go-karting. Ended up paying around $300 for all 4 of us to go race, but my “date” had to stop at the 3rd lap because she crashed with some stranger.
41. What Is That Smell?
Wasn’t my date, but I had gone home with a guy I had been seeing and when we got there his roommate was curled in a ball on the couch looking pretty shaken. We asked him what was wrong and it took him awhile to get it out, but he finally told us what happened: He took a girl home from the bar and they started drunkenly tearing each other’s clothes off as soon as they got through his bedroom door.
She said she was self-conscious though so she wanted the lights off. He switched them off and they started fooling around. She starts going down on him when all of a sudden, the guy notices this horrible smell. He mentions it but she tells him to just ignore it, he’s probably imagining things. Finally the smell is too much so he switches the lights on. That’s when he sees it.
Literal poop all over her and all over the bed. He is completely dumbfounded, doesn’t know what to say or do so apparently all he yelled was “POOP!!!!” She grabbed all her clothes and ran out of the apartment crying without saying a word and, presumably, still covered in poop. He threw his bedding out, took an hour long shower, and refused to go back into his room.
Pretty much ruined our night too. To this day I still wonder what on earth happened—was she into it and was hoping he would be too? Was it an accident and she decided to just go with it? I don’t know which scenario is more horrifying, to be honest.
42. Wearing Herself Out
My worst date was with a girl who spent the majority of our evening together shopping for clothes for another date that she had later that week. It’s kinda funny, seeing as how she was the one who asked me out in the first place.
43. 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.
They weren’t away. 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.
44. Checking Every Box on the Nightmare List
I met a girl. A total 10 to me in every way. I wanted to have an amazing first date because I’ve always tried to make them memorable (after all, you’ll talk about it forever if you end up together). I wanted to keep it simple, nothing too crazy, but she liked coffee. So my plan was basically to take her downtown and we would walk in the beautiful snowfall from coffee shop to coffee shop trying them all until we agreed on the best one!
Oh man, I had the best intentions, but the date could not have gone worse. First, I picked her up and immediately realized I forgot my wallet. So I drive 20 minutes home and search. Not there. Then I remember: It’s at my parents’ house. So I go there and awkwardly introduce my folks to a girl I haven’t even taken on a first date yet.
Finally, I head downtown, only to find that all the coffee shops are now closed. Time to improvise, I’ll take her to a bar or burger joint downtown. Get in there, we had both eaten dinner, neither are hungry…we order a side of fries. Meal cost $4. I felt so cheap, so to make up for it, I take her to the fanciest ice cream place in town to make up for all of this. It too is closed.
Decide to just say screw it. We need ice cream so we walk into the grocery store to get some. I was so panicky while I was in there that instead of getting plastic spoons, I stupidly got plastic forks. So we drive out, park in a parking lot and eat this ice cream with forks because the whole date has gone down the drain anyway. We chat and chat and forget about the ice cream…until I lift up the box and see the worst sight: it’s melted all over the console of the vehicle.
At this point, I called it a night. I cleaned it up, finished chatting, and I dropped her off. No second date surely. Until she texts me “that was the worst first date I’ve ever been on…but I loved every second of it! When can we hang out again?” I was over the moon! And then my car ran out of gas a block from her place so she picked me up, drove me to a gas station, I bought and filled up a gas can and then returned home.
So despite all that, the two of us are together still and in a few months I’ll be proposing. So I guess it turned out alright!
45. When Sharing Is Not Caring
Went on a date with a guy I’d met through a mutual friend. Things seemed pretty normal until we were sitting and waiting for the movie to start. He got his phone out and started showing me pictures of two of his ex-girlfriends. Both women were buck naked.
46. I Spy With My Little Eye
I was at work and a stunningly beautiful woman walked up to me and asked me out. I was in college and she was probably about 25 or 26 years old. It was an amazing date. She was funny and cool and insisted on paying for everything. At the end of our meal, she looked at me and said, “I promised myself I wasn’t going to sleep with you, but I’ve changed my mind.”
Back at her place, things got wild. But something felt off the entire time. She was very particular about positions and what parts of the room we stayed in. She also described everything we were doing in a very loud voice. By the time we were finished, I was creeped out. I knew something was up. On the drive home, I badgered her until she finally admitted that her fiancé had been secretly watching us the whole night.
47. Going On A Date With Your Buddy
A friend set up a double date with a girl he was dating sophomore year of college, and she said she’d bring her friend, who she explicitly said was a female friend. My buddy and I met her and her friend at a bowling alley for rock and bowl. She had brought her cousin. Her male cousin. Who was 15. Then she basically just spent the whole time talking to her cousin and ignoring my friend.
So, me and my friend just had a heck of a fun time bowling and chatting it up with the other people at the alley. Then we all went to get late night appetizers from Applebee’s and she ignored my friend the whole time as well, so we made it our goal to make the waitress/waiters around us laugh as much as possible. My friend and I headed back to his mom’s so I could get my car and told his mom what happened.
She was like “So… you two basically went on a date with each other.” She was right.
48. A Man of Many Interests
I went out with a guy from Tinder who turned out to be legitimately crazy. He regaled me with stories of how he assaulted officers, burned his arm to impress girls, spent significant time in a psych ward, and lost his virginity to an overweight sex worker. He also told me that my eating disorder made him feel better about himself because it made me crazier than he was… He also told me I had obvious acne scars.
After our disaster date, he wouldn’t stop contacting me. He even went as far as asking me to stay in a rented house with him in another city. When I said no, he claimed I had ruined his entire year. I deleted Tinder immediately after that.
49. 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…
The reply I got back…I’ll never forget it. This shy guy ended up sending me a HUGE paragraph back, talking about his creative process for writing (and trying to direct) a specific type of, um, intimate film where women crush rats and tarantulas between their breasts. WHAT THE HECK, DUDE!
50. Slobbering Charming
I took him to a baseball game, where he proceeded to pronounce loudly to anyone and everyone around us that we were an “item.” He pulled out a very large bag of peanuts with the shells and started eating them…with the shells still on. He had pieces of shell all over his face while he kept asking my friends if they wanted any, occasionally spitting up nut particles on them, much to their horror and my extreme embarrassment.
He then tried getting into a full-on fight with me about a hypothetical situation where we would be caught on the kiss cam. “I’m just saying, if we’re on it we gotta go HARD!!” And I was just sitting there cringing and grinding my teeth into oblivion.
He drank so much that he never really even saw the game (had to keep getting up to go to the stadium bar) and he kept asking for my ID so he could double fist his $10 Coors lights. He probably spent $100 on Coors in the first few hours. Not sure why I kept letting him use my ID, maybe it was just shock.
He chugged 2 beers on our way out and kept refusing to let me walk on a certain side of the sidewalk because “A man walks on this side, it’s his duty to a lady.” He started insulting women as we were walking past to get to my car. I was ready to punch him in the mouth, but he was 6’7” and I just wanted to take him home and forget the night ever happened.
He drunkenly started insulting my driving while we were in post-game traffic and kept trying to open the door to get out and drive instead of me. He insults my career, tells me I couldn’t possibly keep up with the “manly” job I have, but don’t worry babe it’s not because you’re not great, it’s just that it’s too hard for you is all I’m saying.
I finally pull up to his house and I’m white-knuckling it to the point where my hands are nearly numb. I tell him to get out and he asks me to come in. I say absolutely not, and he lunged at me to kiss me. He like…sort of… licks? My face? And I literally shoved him out of my car onto the street and sped off.
The next day he texts me, “Hey had a great time! Would love to see you again!” I said, “Your behavior was ridiculous, please never contact me again.” And he responds, “Cool, well if you ever want to get a beer let me know!”
Hard pass. Hard. Pass.
51. Take Me to Your Leader
I once went out with a girl who took me to a cult meeting after dinner. With her parents.
52. Third-Wheeling Myself out of Here
OH man! I was talking to a guy online and we finally agreed to meet for a date. I get there and am surprised to see that there is a woman sitting with him. It turns out that it was his wife and they were looking for a “third.” He never mentioned that during our chats and then called me a prude for saying that I didn’t want to get involved.
53. Making The Date Age Appropriate
I went on a date with a boy when I was about 16. He was older and I wanted to impress him, so I lied about my age. Even though I literally looked 11 and he was in his 20s, he somehow believed me. So the day of the date comes and he says, “Let’s get a drink, yeah?” I felt too weird to tell the truth, so 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. “Uhhh, sorry, I must have left it at home.” I defensively exclaimed. He knew I was lying. 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 at this point and it was nothing but silence until he was like, “let’s go somewhere age appropriate then.” I said, “Age appropriate?” I was shocked, 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.
54. What Type Of Stage Name Is “Brad”?
I met this guy originally at a cocktail bar. We went to dinner on the first date, and then for the second date we went to a Comedy club. The first problem was he kept nudging me when I laughed, like I was embarrassing him.
Of course, I was irritated by this, but tried to tone it down since I still had two more hours to sit through. Halfway through, he’s just acting real nervous and then the MC gets up on stage and says “Welcome Brad to the stage”… The guy I am on a date with is not named Brad. Brad is his stage name.
He goes up on stage and proceeds to make two incredibly offensive jokes. Tables turned. I was embarrassed and nervous for the rest of the show. Joke was on me. We didn’t go out again.
55. More Than A Hike
Years ago, I met a girl online and after we’d approved of each other’s photos and list of interests, we talked on the phone and hit it off right away. She lived about and hour away, and she said she wanted to go to a local national park and go hiking and have a picnic. I get to her house to pick her up and see that she has packed a tent, sleeping bags, a cooler, and basically a full weekend worth of camping equipment.
I told her I thought we were just going hiking and she said “I figured we could just camp out overnight. Just get me back home in time for church in the morning.” So we head out, we set up the tent, go for a hike, swim in the lake, have dinner in the lodge, head back to the campsite, make a fire, and settle in for the night. Later, in the tent, stuff starts happening.
After awhile she says “Can we wait a bit on that, and just go to sleep.” I oblige and we sleep. In the early morning hours, she wakes me up by making it very clear the wait is over. After we finish, she starts crying. She apologizes and says she’s not ready to be in a relationship. I tell her I understand but I’m pretty confused by this point. Looking back, that was just the beginning.
We pack up everything and I drive her home and drop her off at her house. About 15 minutes later, I get a call on my cell phone. It’s my dad. He asks “What on earth are you doing?” I tell him I have no idea what he’s talking about. He says “The Sheriff’s department just came by here looking for you and asking if I knew your whereabouts. You’re wanted in the disappearance of some girl. Her family said she never came home last night. They went to your place first but nobody was there.”
Apparently, she wasn’t home for church and her family freaked out. I called her and told her to please contact the Sheriff and let them know she was not, in fact, kidnapped. She laughed and then called them.
We never had a second date.
56. 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.
57. A Series of Unfortunate Events
I witnessed a couple on their first date having a few drinks. They started making out by the third drink. The dude cried by the fourth drink, then started sucking on her finger. Then he cried again. Next thing I know, he abruptly ran out of the bar, and down the street. She paid.
58. Oh, Look At The Time
A couple years after my divorce, I matched with an Indian (as in, not Native American) woman on OkCupid whose username included Pocahontas in it. Immediately, I assume this woman has a great sense of humor, and we have a couple days of great conversation and decide to meet up at a bar. It went so much worse than I planned.
When we meet, she’s much more awkward than she was via text, which happens sometimes, so I think nothing of it. That is, until about a half-hour into the date when she reveals that we hadn’t actually been talking on OkCupid and that her friend had been doing all the messaging because her friend didn’t trust her not to mess it up when she was talking to a guy.
I think that’s weird, but I figured I was there, so I may as well try to get to know this person. Then, maybe an hour in, she starts asking me about my divorce. I don’t mind a couple questions, but she starts grilling me. Then she starts lecturing me about how Americans don’t understand what marriage is actually supposed to be.
THEN she starts telling me about all of my moral defects that obviously led to my divorce. Finally, she also tells me that because I wasn’t financially secure (I was still working on my PhD), that I shouldn’t be dating anyway. Finally, I just cut her off, held up my wrist, pointed to my watch, and told her I totally forgot about something I had to do.
As I paid my tab and walked out, I realized I didn’t wear my watch that day. Even so, NO regrets.
59. This Funny Feeling Inside
I was so nervous I threw up on him. No second date.
60. Mommy Dearest
I work at a bubble tea restaurant right near a college. A lot of first dates happen here. Probably the worst I’ve ever seen was this guy who looked somewhere between 17 and 19 years old. He was meeting up with this girl around the same age. They got teas, took a seat, played a board game, and talked. Here’s the catch though” His mother sat at the table next to him the entire time, and just stared them down.
It made me feel so bad for him—but the icing on the cake is when she goes up to them at 8:30 pm and tells them that it’s time for the two of them—her and her son that is—to head home. The guy is visibly upset, but says goodbye to his date, and follows his mom out. The girl comes up to order another tea, and I asked her about it. She was more than happy to fill me and the other girls in. This lady had essentially injected herself into the date, interrupting their conversation and critiquing her son’s behavior.
61. 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.
62. What Do You Recommend?
My story takes place in a really lovely, cosy steakhouse during dinnertime. A couple came in, obviously on a first date. The woman looks over the menu, quietly closes it, and reminds the man that she is vegetarian. The menu is very much built for carnivores, which I think is fine given it’s a steak restaurant. But the man’s reply stunned me.
He responds with, “That’s okay, because we’re both getting the kids’ menu macaroni anyway.” He went on to explain that this kids’ menu macaroni is “so, so good,” and insisting that she order it. Her face fell. This was a very serious-looking woman who clearly went all-out for this date in terms of her attire and all.
She was also much more attractive physically than he was, and clearly did not expect to be eating a bowl of macaroni for dinner. Nevertheless, she was very polite and didn’t voice any objection. They ordered the macaroni and barely said a word to each other all night. The staff could hardly keep from giggling while watching this play out.
63. Date Like A Train Wreck
I was hanging out at Starbucks and witnessed a horrible date. She was Japanese, and he started off by showing her his shirt with sumo wrestlers on it, then would ask questions like: What’s your favorite sushi? Do you only speak Japanese? How do you say toilet in Japanese? They have sumo in Japan, right? Did you see my shirt?
It was so amazingly awkward that I bought another cup of coffee to listen to the entire thing.
64. Wine About It
I worked as a waitress in an Italian restaurant. One night, an obvious first date comes in, and from the get go, the guy is a nightmare. He kept making comments about the girl’s order, such as how fattening a dish would be, and then proceeded to brag about how his family owned a vineyard, and he knew a good red wine when he smelt one. To prove it, he ordered the house wine and the most expensive wine on the menu, then talked about how the bouquet was different, and the clarity was so much better on the “expensive” wine.
When it came to dessert, he told his date that she shouldn’t have any, or she’d end up with stretch marks. I could tell she was already over it, but this was the last straw. She stood up and yelled at him for being a condescending jerk, for knowing fudge all about wine, and dropped the coup de grâce that her father was our wine supplier and that the house red was exactly the same as the most expensive wine—all of which was totally true.
He was left speechless with the full check to pay.
65. 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.
66. Look Out for Each Other
I was the person on a terrible first date. It was unusual because he picked a very fancy location that was way out of town—like an hour drive. I normally prefer casual dates like walking in the park or coffee, but he insisted we go. I arrived first, and when I sat down I ordered a drink—strawberry lemonade, as I don’t drink alcohol—and was talking to the waitress, saying I was waiting on a date.
She was super nice to me and said, “Oh, I hope it’s fun, good luck!” Once he arrived, suddenly her mood shifted, and she gave him an attitude when he ordered. He was trying to pressure me into getting some alcohol, but I was firm and said I would stick to my strawberry lemonade. Throughout the date, he kept trying to order me vodka.
The waitress was being really weird and kept complimenting me, giving me free lemonades, refills every two minutes, and basically giving him dirty looks. She stayed close by always watching. The guy was being a jerk about the situation, and started acting rude, saying, “I hope she’s not gonna charge for those.” He looked incredibly angry and uncomfortable.
I was starting to wonder why this waitress was being so mean, so I went to the bathroom and waited to flag her down. That’s when she told me the truth. It turns out my date went there every other weekend with a new girl, and that the girls would walk out of there acting very drunk, she suspected he roofied them, and wanted to make sure I was okay and kept changing my drinks to make sure I wouldn’t get screwed up.
I did confront him, and demand he empty his pockets, he didn’t have anything, but admitted he pressured drunk girls into sleeping with him. I took off right when he said that and the waitress took me to my car, I made sure to give all the cash I had as a tip. I seriously love that waitress, and I’ll never forget her.
67. Give Me a Call
Out at dinner, night is going well. Some guy pulls up a chair to our table. Introduces himself as her husband. I got up and said sorry did not know. Girl called me later that night, said I could pick her up as she was single now. What a rollercoaster.
68. My Mistake
I was on a first date with a girl I also worked with. We’d been flirting for weeks and had wonderful chemistry. Our date was great and had a life of its own. She drove. At the end of the 6-hour long date, we were sitting in her parked car in front of my house, continuing the captivating conversation. We had a work meeting the next morning, so when it came time for me to go, I started to exit the car and said “See you tomorrow.”
She coyly said, “I can’t wait that long.” Without thinking, I replied, “Well, you’re gonna have to,” and slammed the car door. I didn’t realize what she meant, or how what I said came across, for some time, like the next day.
69. Baby It’s Cold Inside
I once met up with this young woman for dinner. She was never married and had no kids. She got super weird and ended up saying a lot of crazy stuff. I could write an entire story about the evening, but here’s the kicker. At one point, I saw her eyes light up as she apparently remembered that she hadn’t told me something important.
“OMG, I haven’t shown you my daughter!” she shouts out. “Hmmm, what’s this all about?” I wonder. I thought she said she didn’t have any kids. The woman then reaches into her purse, pulls out an old Polaroid photograph, and hands it across the table for me to have a look at. I was not at all expecting to see what I saw next.
It was a picture of her sitting in a hospital room chair with some guy’s arm over her shoulder, both smiling at the camera. They were holding a stillborn baby! At this point, I had no reaction. It had been three hours into the night and an ever-increasing string of surreal events had broken my level of interest. I just handed the photo back and said, “I’ve got nothing to say about that.”
70. Let’s Go Somewhere Private
It wasn’t really a date, but I hooked up with a guy (friend of a friend) who I met in a bar close to where my parents lived. As I was home from college and he was too, we couldn’t go to either house to “get to know each other better.” So, on the drive to drop me off, I suggested we pull in to a deserted parking lot in front of what looked like an automotive shop.
Not 5 minutes later while we were distracted, the cops pull up. They suggested we not choose the municipal garage where all the extra cars are as a place to have some private time. Oops.
71. A Storied Romance
I once decided to try online dating. The guy I went out with had looked pretty cute in his picture. He showed up to my house when it was time for the date. He did NOT look anything like his picture. I later came to find out that the picture was him from five years earlier—and that he had gone through a BAD case of adult acne since then, which was still plaguing him.
We went to Long Beach and he said he wanted to go to Ruby’s or some other diner like that. As soon as we sat down and the waitress had handed us our menus, he informed me that he only had a little bit of money on him (something like $20). I inferred that this meant I had to order something cheap.
I ordered a basket of fries and a glass of water. He then proceeded to scarf down a bacon double cheeseburger, onion rings, and a strawberry malt—in addition to about 75% of the fries I ordered. I wish I was joking. Throughout the meal, he repeatedly lamented his last girlfriend, who had recently left him. He was practically in tears over the fact that she didn’t love him anymore, and he told me about how he wanted her back so badly.
I sat in stony silence the whole time. Clearly, I was just intended to be a sounding board to him. The date wasn’t really a date. It was a hostile kidnapping in which I was starved and had to listen to the ravings of an idiot.
72. Putting on a Show
The worst date that I ever went on was the one where my ex-boyfriend took me to see a play about the women’s liberation movement. Afterward, he informs me that the purpose of this outing was to give me confidence because he was planning on breaking up with me. I literally had no idea how to react. I had never experienced anything as ridiculous as that in my life.
73. Two’s Company Three’s A Scene
One time I had two women arrive together. I figured they were just out for drinks, but noooope, I was so, so wrong. They requested a special table with a window looking out to the bar. As I serve them drinks, uddenly one of them stands up, and runs around to the bar side. Apparently, she and her friend were scoping out her husband and caught him at the bar with another woman.
She starts yelling and cursing at them, and the husband and “other woman” leave. She followed them into the parking lot shouting, “YOU FREAKING LIAR.” I got a bad tip from the two women, but it was worth the show at least.
74. Standing On The Corner
I asked a girl out in late spring, so we decided to walk around outside. It was nice out and she went to a different school than I did, so she showed me around campus for a while. It was pretty interesting. She was probably slightly out of my league, but I thought things were going well. We decided to grab a bite to eat at a place in the nearby bar district and sat outside.
Halfway into the meal, a local wanders down the street playing a harmonica and just rocking out. We barely even noticed him because things were going pretty smoothly. We had just discovered that we enjoyed the same kind of music and were deep into a conversation about that. Then, all of a sudden, we hear a lot of shouting and swear words.
We look over to see that another local man had appeared on the scene, angry at the first guy about who owned that particular spot of the street corner. The fight got pretty heated. We tried to ignore it, but it was slightly impossible as they were only about ten feet away from us. I still can’t believe what happened next. All of a sudden, the second guy pulls out a knife and stabs the first guy in the neck.
He passed really quickly and blood was everywhere. It was horrific to witness. We were then questioned by the authorities and had to make statements and everything. It basically ruined the entire evening. Somehow, I got one more date out of this girl, but we just struggled to make conversation at that point. After witnessing a murder, things were just really anticlimactic.
75. Double Whammy
I once took a girl out for sushi as a first date. About ten minutes into it, I got a call from my boss. Ordinarily, I wouldn’t have taken the call, but this is not the kind of guy that you can ignore without some major consequences. I went outside to take the call where the guy berated me throughout the entire conversation. Great—but it gets worse.
He ended it by saying he’s sorry he interrupted my dinner but he’s not sure I understood what it takes to be his assistant. I walk back in, my confidence utterly destroyed, and proceed to be completely in my own head for the rest of the date. As I dropped her off outside her house, she says, “You might be the most awkward person ever.”
The next day, I was fired.
76. Leaving So Soon?
I once went on a date that seemed pretty decent in and of itself. Then, after I went home, she continuously hung out in my parking lot for over two hours after she dropped me off “in case I changed my mind about doing something after dinner.” Umm, if the answer to that wasn’t a definite no before, it certainly is now…
77. A Previous Engagement
I once met up with a woman for a blind date and a little bit into our conversation, she suddenly got excited and asked me to congratulate her. When I asked why, her response made my blood run cold. She said, “I just got engaged last weekend!” Ummm, what??? Then what on earth are you here with me for?? I swear, there are some people whose brains I will just never understand…
78. Father’s Day
It was grade 11, and I had just moved to a new town. I quickly became attracted to this one girl and would’ve given anything for a date with her. We got paired up to be partners in our “Food and Fabrics” class, and I totally pulled out all the stops. I was doing whatever it took to get a date with this girl. It was all I cared about.
In the class, there were a couple of projects where you would have to sew a pillowcase or a pair of pajamas. My family didn’t have a sewing machine, so we would do the projects at her house. Upon these visits, I began to question how badly I wanted this girl. She lived in what appeared to be a wood cabin, and her father seemed legitimately insane.
The walls were lined with animal skulls, the guy was a devoted hunter. He had bear-skin rugs and antlers all over the place. He would always walk around with his shirt off, drinking a Budweiser, chewing snuff, carrying a deadly weapon. He never spoke a word to me. The whole experience of being in that house just felt extremely weird.
By this time, I was starting to gain some friendships in the school, and one of the guys I met named Neil noticed that I’d taken a liking to her. He then asked me if I’d heard about her parents—and let me know the jaw-dropping truth about them. He proceeded to tell me that her father had taken her mother’s life and gotten away with it. Her body was found in the middle of town, pumped by a couple of rounds from a weapon exactly like his.
He got off on the charges due to a lack of proof, and the girl had to live with him because he was her last living relative. At this point, I was like “What in the world???” The story made no sense, and I wasn’t about to believe it. It definitely kinda rattled me, though. But there was no way that I was going to bring it up to her.
Anyways, a little time passes, and I ask her out. I go to her place to grab her, and she’s gorgeous. Her dad makes a comment about, “You know what’ll happen to you if you touch her,” and suddenly the story is the only thing I can think about. We went skating, then to a movie, but I was terrified the whole time. I just couldn’t get the thought out of my head that her dad was going to attack me when we got back to her place.
So, after a sub-par date, I start the long drive back to her place. We get to the end of her driveway and she gets me to park and turn off the lights. She wants a kiss. At this point, I forget all about her dad. I lean over, and put some moves on. After a few minutes, we stop and I turn the lights back on. There’s blood in the snow at the end of the driveway.
I wanted to say something when I noticed this, but I didn’t want to sound like a scaredy-cat. Her dad was a hunter, right? I’m sure there’s a logical explanation. I put the car in drive, and start the winding trek down her driveway. The trail of blood seems to be getting thicker, and I’m getting more freaked out with every passing second. She still says nothing, as she’s fixing her hair in her mirror.
I keep driving. More blood. I turn the last corner of her driveway, and see my headlights shift from the trees to her father. Standing in the middle of the driveway. Covered in blood. Blood all around him. Huge knife in his hand. And what appeared to be a naked human body lying at his feet. I start hyperventilating. Suddenly, I’m crying, and don’t know why.
I pee my pants right in front of her. Her dad takes me to the hospital. Turns out I have had mild-asthma for my entire life and had a panic attack that triggered it. Apparently, the dad had found a bear at the end of the driveway, shot it, dragged it down the driveway, and skinned it before we got back. But that’s not even the craziest part—the girl’s mother was still alive and lived just a few blocks away! That guy Neil totally wound me up.
Once we cleared everything up, everything somehow turned out okay. This happened a little over three years ago and I’m still with the girl. Her dad makes fun of me all the time, except we’ve gone on hunting trips together and I’m pretty sure he’s secretly a fan. Neil was just a jealous ex with a wild imagination. Her parents had simply split up. And her mom turned out to be pretty awesome too.
79. Please Don’t Hold My Hand
I saw a couple in their mid-20s come into my work. It’s obviously a first date, but they seem to really like each other and are getting along well. However, I wasn’t serving them, I was serving the table next to them. About halfway through their meal, I notice them holding hands over the table. Cute. Then, the guy lifts her hand to his lips and kisses the back of it.
A bit of an outdated gesture, but still cute, I guess. The woman seems slightly confused but goes along with it. A little while later, I see the guy do it again. Okay, dude. Then again. The woman is confused and looks a little uncomfortable. They are no longer holding hands. I go to serve my table and see the dude full on MAKING OUT with her hand, tongue and all.
The woman looks extremely embarrassed, and uncomfortable, looking everywhere but at her date. I go over, and casually ask if they need anything, and the dude stops. Woman yanks her hand back. She left pretty soon after.
80. Nice Car, Awful Guy
My mum went on a date with a guy who picked her up in a fancy car when she was young. She pointed out a cute rabbit eating grass near the side of the road, so he sped up and hit it on purpose trying to impress her. Instead, she cried and made him take her home instantly. She met my dad not long after.
81. Fire and Ice
First date. We went ice skating. She fell. I accidentally skated over the back of her hand. The blood on the ice was a sight to behold. She wouldn’t speak to me as they put her onto the stretcher and took her away. The last I ever saw of her was as the ambulance doors closed. Needless to say, I did not get a second date.
82. Show Off Your Interests
A couple of years ago, I was tending bar at a high-end steak joint. A pretty brunette walked in and sat down at the bar. After fixing her a cocktail, I asked if she’d like to see a dinner menu. She explained that she was waiting for a date. A few moments later, the guy arrived carrying a large bag. It was immediately obvious this date was their first.
Their conversation was lurching from forced, to downright painful when he reached into the bag and pulled out an album containing…his Pokémon card collection. He set the book on the bar and thumbed through each page, thoroughly, and lovingly describing every card, attempting to educate his date in the ways of Japanese pocket monsters.
I’ll be fair to the guy—dude was passionate. She feigned an emergency, and called her friend to pick her up. He stayed and ate a plain hamburger at the bar.
83. Every Man’s Dream
My friend had a Match date where the woman drank a bunch, and as they were walking back to his car so he could drive her home, she asked him to “Wait right here.” He thought maybe she was making a phone call or had to throw up, because she walked into an alley. Then she spread her legs and began peeing from under her skirt, spraying all over her legs and the wall of the alley, after which she called to him, “Is this turning you on?”
There was no second date, and he scrubbed out his car seat with Mr. Clean.
84. First Is the Worst
My worst first date was also, by far, my first date ever. I was only about 14 or 15 years old. The girl I liked asked me if I wanted to go on a date, I was over the moon. She told me to meet her at the park. When I got there, she was there with her friends and they all laughed at me for thinking she would ever want to date a loser like me.
85. Getting It All Out On The Table
Met 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, when “we” are married, and as though that wasn’t bad enough, it got worse.
She went on to talk about 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 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.
86. 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.
87. Selling Your Soul
I went on a coffee dаtе with a girl frоm Tіndеr. Halfway through, she pulled out a bunch of samples of some herbal tea product and started telling me all about why I should buy some from her. I essentially went to a sales pitch and paid for the coffee.
88. Dining and Diving
We went to a fancy restaurant. The girl claimed that she was going to pay for her half of the bill. When the check comes, she asks to use the bathroom. 10 (very awkward) minutes go by and right when I’m about to text her she zooms out of the restaurant, leaving me with the check. Plot Twist: I banged her friend, so I’d say we’re even.
89. A Portrait Of The Artist As A Young Woman
I took this artsy fartsy girl to a theater for a play. Cool, whatever. Afterwards, we’re walking back to my car and everything is going normal. Small talk and all. She suddenly breaks down into tears and cries about missing her ex. Darn. I guess we’re not getting Chinese food anymore. I take her home. She lives in boonie-ville. Foggy as heck at night. I drop her off at home, thinking I’m never taking her on a date again. Head back home. Phone loses signal because boonie-ville. I run a red light because of the thick fog and the GPS starts going nuts. I hit another car and total my car.
0/10, would not go out again with an artsy girl who was secretly still stuck on her ex at the cost of an entire car.
90. 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.
91. Eating For Two
I chatted a girl up online for about a week or so, and things went pretty well, so we decided to meet up. I asked her out for dinner, and said that if things went all right we’d go grab a drink. Let’s just say her photo didn’t match her appearance. Her excuse was that she had a crazy ex who was stalking her, so she used her sister’s photo and name.
HER NAME!!! SHE LIED ABOUT HER NAME! Anyway, come to find out through our “interview” that she was an only child. She didn’t catch her slip up, but I sure did. She rambled on and on and on about stuff I really couldn’t have cared less about. Then came the food. The waitress may as well have brought it out in a trough, as this woman didn’t use her utensils.
Did I mention we were at a steak restaurant? That’s right folks, she picked her steak up and ate it with her hands. Let’s not even get into the potatoes. It was the worst date of my life. I couldn’t eat my meal. I told her I wasn’t feeling well and that I was just going to get my food in a box to go and I’d eat it later if I felt better. Her response: “Would you mind if I ate it?”
She proceeded to devour my dinner as well. The waitress comes over and says “Goodness. When is your due date?” So she says that she is due in two months. First off, I couldn’t believe the waitress asked that, but then I was floored at the girl’s response. Unbelievable. Being the gentleman that I am, I picked up the check because hey, it wasn’t going to pay itself. I kindly said it was “nice to meet you,” got in my car, and went to the bar. Well, she followed me.
She followed me to the bar, and when I got out of my car, she proceeded to berate me over why I was going out instead of going home. Now she’s calling me a liar in the parking lot of the bar I frequent, and my work buddies are starting to roll in. I never heard the end of it. I said to heck with this, got in my car, and drove home.
92. Too Young For This
I was 22 and out at a bar, started talking to an older woman (mid-30s) who seemed really nice and really into me. She reassured me that she was single and just looking for some fun, so I thought why not. We went out back, had a bit of fun and swapped phone numbers. I was feeling pretty good about it until I learned four things;
- She is a close friend of my mum,
- She is married,
- Her husband is a law enforcement officer.
- And she has two children.
As you can imagine, I was mad. I sent a text saying what we did was a mistake, that I’m sorry but I don’t want to see her again. At that point I thought the worst was over… I couldn’t be more wrong. Later that night, I get a phone call from my mum, her friend has just tried to commit suicide and that I had to go pick up my mum (she had been drinking) and drive her over to the friend’s house ASAP. At this point, I am furious, but I man up, get the car, pick mum up and drive over.
As soon as I arrive, mum jumps out and runs to the house, saying that I should stay in the car. Two minutes later, the first officer arrived (which turned out to be her husband on call), couple of minutes after that two more cop cars arrived and an ambulance. The woman is brought out on a stretcher and mum tells me to go home as she will ride in the ambulance to the hospital.
The woman ended up surviving, and I felt like utter trash over the whole scenario. I knew that I hadn’t intentionally done anything wrong, but it just got so messed up. I found out later that her one of her two kids was in the room with her that night.
To make matters even worse, she then proceeded to abusively text me over the next two years as well as confess to my own mum that I am “the one for her”. Her text messages ranged from overtly sexual to incredibly insulting, and I ignored and deleted every single one of them. In hindsight I should have kept them as proof, but I couldn’t bring myself to keep them.
Moral of the story: Be careful who you hook up with.
Not only was my blind date two hours late, she also showed up drunk—and then I found out that was her “good” behavior. She took me to a bar after we saw a movie, only for the dark truth about why we were there to slowly dawn on me. It was a gay bar and she spent the rest of our date trying to get me to admit I was gay. I flirted with the gay bartender to make the night less awful.
94. The First Cut Is The Deepest
It was the first date I’d ever been on. I wasn’t the most talkative guy in school, but I rather fancied her so I worked up the courage to ask one day—and to my surprise, she said yes. We were both 15/16 years old at the time. I get a ride to her place from my mom, we pick her up and head over to this restaurant in one of the classier parts of town.
We get dropped off, head in, make light conversation and I find out she’s never been there before. I’d only been there once myself for my birthday, a year or two ago. She asks me to order for her and I do so; two steaks with the trimmings. Anyway, things continue rather pleasantly and our food arrives. We dig in and continue to talk but I notice about 15 minutes in that she’s gone a little cold on me and she hasn’t yet touched her steak. She’s picking off the veg and potatoes around the side, but the steak is untouched.
My natural reaction is that I didn’t ask if she had any dietary restrictions; so, I apologize immediately and ask if she doesn’t eat meat. Her response is so disturbing it’s unforgettable. She says she does eat meat, but: “I’m waiting for you to cut up my food for me!” Apparently, at the age of 15 years old, she’d never once had to eat a slab of meat that wasn’t first cut up for her by either her parents or whomever else she was with at the time.
I was surprised, but I taught her how to cut up her own food—seriously, girl didn’t seem like she’d ever held a knife before—and afterward, we dropped her off at her place in silence. So…thus ended my first date, and last date with her.
95. Taking The Term “Blind Date” A Little Too Far
Not sure this counts since the date didn’t actually happen, but I was set up on a blind date. We planned to meet at a restaurant. I got there first and since it was a nice day out, I sat down on a bench outside the restaurant. He ended up calling me on his way over and I told him where I was sitting. He was still on the phone when he started walking up to the building.
He took one look at me, hung up the phone, and walked back to his car. I tried to call him back, thinking something must have happened, and he didn’t answer. No more answers to calls or texts afterward.
96. 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.
97. He’s Not All That
When I was 15, I went abroad to Germany to study for a year. I was an awkward, anxious, nerdy girl and didn’t make any friends, though one charitable soul offered to set me up on a date with a guy she knew from another school. I’ve never been the dating type, but I went along with it in hopes that it might crack some of the boredom, and what the heck, maybe this guy and I might hit it off.
Fast forward to date day, and I ask the guy what he wants to do. It’s a small suburban town just far enough outside the nearest city for it to be a pain to commute to, and not big enough on its own to offer much in the way of entertainment for two teens on a blind date. This guy, Kalle, suggests going for a walk. Fine, I’m down with that.
So we walk around, grab a coffee, and talk for about an hour or so. That’s all the time I need to settle any doubt that this guy is not for me. He’s not a bad guy, he just lacks even the faintest glimmer of intelligence. I ask him about his hobbies, and he tells me that he’s interested in pipefitting because that’s the vocation he intends to go into at his father’s request, despite his own indifference.
I ask him if he likes to travel and he says no, but he’s traveled a bit in his life. Where did he travel? About 45 km west of the town he grew up in, when he got lost and accidentally crossed the border into the Netherlands on his moped. He then launches into a tangent, completely out of nowhere, about how women can’t and shouldn’t be allowed to operate motor vehicles. (Hypocrisy much???)
At school the following week, the girl who set me up with this guy asked how everything went. I tried to be as diplomatic as possible and said that he seemed like a nice guy, but we didn’t have much in common, and thanks for making the effort, but I’m not interested in a second date. This is when I found out the awful reality of the situation.
My host sister, who’d tormented me in subtle ways from pretty much within a week of my arrival, then joined my classmate and they both collapsed in paroxysms of laughter and high-fives. Apparently, the two of them had arranged this date as a prank, and had a bet with each other about if I would go on a second date with this guy.
And if I had slept with the dude, well…I don’t know. It never would have come to that. Needless to say that, upon learning of this scheme at my expense, I unleashed some serious fury.