Mortified People Share Their Worst First Date Stories

May 1, 2023 | Rachel Ramlawi

Mortified People Share Their Worst First Date Stories

The dreaded first date. Has anyone ever had one actually go well for them? They only ever seem to range from pitifully awkward to "woke up in a bathtub full of ice missing a kidney". The good news is that they really do make for great stories. What’s the opposite of a meet-cute? The folks over at Reddit have shared with us the first date disasters they’ve either been on or witnessed happening, like bystanders to some terrible disaster. Here are the most mortifying terrible first date stories.

1. 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.

worst first date

2. Empty Your Pockets

The most awkward first date? When his wedding ring fell out of his pocket midway through dinner.

Worst First Date FactsPixabay

3. Bring a Spare

A guy and a girl are sitting at the sushi bar where I worked. They both order miso while they look at the menus, the waiter goes to take the rest of their order, and the guy picks up his menu and flips both bowls of miso directly into their laps. I hear him apologize, and he runs to the bathroom, so I help the poor girl clean up the miso and herself.

He comes back and says he has to go get his spare pants out of his car. He returns five minutes later in dry pants, and they power through the awkward rest of the date. Honestly, I had so many questions.

Worst First Date FactsFlickr

4. Best to Keep Your Mouth Shut

I once went on a date with a man who had no teeth. We met on a dating website, I had no idea because in all of his photos his mouth was closed. I wasn’t even as bothered about that, as I was about the fact that he kept going on and on about his "best friend," who was a 15-year-old girl that lived next door to him. It was weird.

How great she was, how much time they spent together, and about how no one, "understood their relationship". Mind you, he was in his early 30s. I stayed through the whole date, but let him know I wasn’t interested in a second. NOPE.

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5. A Few Drinks Too Many

I’m not a server, but as a bartender, I’ve seen my fair share of very bad first dates. My girlfriend was serving an obvious first date, and they were ordering an alarming amount of drinks within 30 minutes of sitting down. I asked my girlfriend what was going, and she said the girl was doing all of the shots they ordered.

I walked from behind the bar to the bathroom purely to check in on the situation, and good lord this girl on the date was blasted and just saying curse words constantly. Eventually, the chick went outside to smoke, and the dude went straight to the bar and asked if he could give me money for the waitress, and sneak out—he actually gave $200 for a $70 tab, so nice.

The girl came back in, ate the food they ordered, then tried to order more drinks. I had to throw her out, and she started calling me racial slurs—I'm very much a white dude. A bizarre weird night that my girl and I still talk about years later.

Worst First Date FactsPxHere

6. Save It for Later

Oh man, thanks for asking this one, I've got a great one. 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 inebriated.

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.

He's a really nice guy, he's come to the place I work now a few times.

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7. Narcissus Meets His Match

I often eat and drink alone and people watch, and first dates are almost always painfully obvious. The worst one I ever saw, two people who were probably perfect for each other; they were both completely self-absorbed. How completely? They both started stories and kept telling them at the same time. They weren't even listening, just talking at each other.

I was enraptured by the sheer insanity of it, I didn't eat for like 45 minutes as they both just yapped away, barely stopping.

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8.  Quick Trip to the Bathroom

This isn't as bad as some of the others, but the guy and girl arrived separately and it seemed like they were meeting for the first time at the restaurant. They sat down, then the girl excused herself and went to the bathroom. The guy ordered drinks for them both while she was gone then, after like 30 minutes, ordered two meals.

It was so obvious she wasn't coming back, but he kept calling her, and eventually just left all the food and drinks untouched, and paid the bill.

Worst First Date FactsShutterstock

9. Pick a Good One

When my date complained about the selection at a place with over 50 beers on tap, because they didn’t have a specific one he had, "while doing a peace mission," which was actually just him taking a vacation and staying on peoples couches that he met off the internet in Central America. He also was super judge-y about my taste in drinks, music, food, hobbies, and career.

Too "corporate" and too "mainstream". He also was just a huge tool bag in general—he didn’t even offer to pick up the bill. Like not even his half, I’m fine with going Dutch. He then took a bunch of my leftovers home. that he didn’t pay for!!! Another time, a guy told me he really liked to snuggle with his mom. He was almost 30 years old.

Needless to say, I’ve dated some winners.

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10. Injured on the Date

During my first date with my now-boyfriend, he reached across the table, and hit a ceramic mug which flew off the table, and shattered onto my unsuspecting toes. I was picking ceramic shards out of my foot for the rest of the day...

Worst First Date FactsPexels

11. Knock Em Back and Knock Em Out

I bartended for a decade. For a while, I was at a mid-range Italian restaurant. More than once I saw a first date go awry because one of the two drank too much. The most memorable one was a woman who started downing rum punches. They were at a table, so I couldn't see them, and I guess the waiter had forgotten his "red light, yellow light" training—I don't know if they still do that.

After the sixth one, I asked if these were all going to the same person, and he said yes. I was like, oh snap. Sure enough, the girl ended up puking all over my bathroom and locking herself in. When we got the door open she was passed out, and there was puke everywhere, including all over her. No cab would touch her, so the guy ended up taking her home.

He came in a week later and said they were going on another date. I was skeptical. They've been married for about 15 years, and are absurdly happy. She avoids rum punch now.

Worst First Date FactsShutterstock

12. Up and Left

I work at a pretty high-end steak house. I got sat with a table of two, and when I greeted them, I assumed they were a couple. It took them quite a while to order their food—I had to go back quite a few times and ask if they were ready. After an hour of them talking, ordering cocktails, and looking at the menu, they finally ordered.

The woman ordered a filet mignon, and the guy ordered our most expensive steak. Right before their food came out, I saw the guy get up, and walk towards the bathroom. My coworkers ran their food to their table, and the woman sat there with all the food in front of her. I thought he was coming back soon, but around 20 minutes went by, and there was no sign of him.

My manager walked over to me, and asked me what was up with them, I said the guy was in the bathroom. My manager went and asked her if she wanted us to keep the food under the warmer. She said yes, and the food was under the warmer for maybe an hour while she sat at the table alone. I walked over to her and asked if everything was alright.

She immediately broke down, said it was their first date, and that they met on Tinder. Apparently, she told him that a steakhouse was a little much for a first date, and suggested coffee instead, but he said no. As they were sitting there talking, he looked at his phone and said, "my daughter has an emergency," and he quickly got up and left.

She was texting him after, and he never replied. This girl bawled to me for 20 minutes, repeatedly saying, "what's wrong with me?" and I had to reassure her he doesn't know what he's missing, blah blah. I went over to my manager and asked what we should do about the check. He said he was stuck, because it was a $250 tab, and that's too much to just not have her pay.

After a few minutes of convincing him, I got him to take everything off the bill. I boxed up all the food (including his steak and sides), brought it over to her, and told her to enjoy her night. She stopped crying, thanked me, and left. After writing this, I'm now wondering if they swindled me.

Worst First Date FactsGetty Images

13. Gone Fishing

There was this young guy eating dinner with—what I thought was—his mother. I noticed that they seemed weirdly uncomfortable, and distant but didn't think much of it. Turns out the lady was not his mom. He had met her on a dating site and had been VERY clearly catfished. The lady was at least a good 20 years older than him.

When she left the restaurant he stayed behind, and told me about what happened, then asked me out. I politely declined but agreed with him that that was a really weird situation.

Worst First Date FactsShutterstock

14. One Man’s Great Date is Another’s Terrible One

I’m a bartender at a popular restuarant. I had an older gentleman—about 60 years old—come in on a Wednesday evening and order a bottle of vino and two glasses, as he’s waiting for someone to show. This other older woman shows up a short while later, and both of them hit it off. They sat right behind my register so basically anytime I had to ring something in I had a front-row seat to their date.

Both of them crush three whole bottles of wine and sit there for more than four hours talking away. Around the fourth hour of them sitting there getting sloshed, they both started making out randomly and would not stop. They started sucking faces with uncomfortable intensity, somewhat terrifying all my bar guests, and myself.

At one point the older fella leaves for the bathroom, and his date proceeds to let me know it’s their first time meeting. Not entirely the worst first date for them I suppose, but definitely was for me and the other customers.

Worst First Date FactsShutterstock

15. Hot Date!

Me and my girlfriend sat next to an obvious first date at a Pan-Asian fusion restaurant. She comments that her main course wasn’t quite what she expected, and thought it’d be spicier. He then snaps his fingers above his head, VERY loudly, so half the restaurant turns round to look, and a waitress rolls her eyes and goes over.

He demands that they COOK IT AGAIN AND MAKE IT HOTTER. Next thing, there’s half a dozen Thai waitresses around the table calling him worse than dog waste in Thai—my Thai girlfriend translated—causing a massive scene while his date’s face turns red, and they take her plate away. She then has to sit with no food while he continues eating.

He eventually realizes he’s messed up, and stops eating, but she sarcastically tells him to enjoy his food. They brought her a fresh plate and they eat in silence. First—and I’m sure the last—date.

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16. 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.

Worst First Date FactsShutterstock

17. Bad Luck at the Bus

I am open to anyone, regardless of gender, but this was with a dude. I met a gent while waiting for a bus, we chatted for a while, and he tried to impress me with his playing of the stock market, but I gave him the benefit of the doubt. I actually thought, "why not," and we exchanged numbers. We arranged to meet that night and go to dinner.

There was an arcade I frequented, so we'd go there after. He picked a buffet near where I worked at, it was like 4.99 to eat there—and you DEFINITELY got what you paid for. I was really into goth culture at the time; when he met me on the bus, I was dressed for work, so he seemed confused about my attire. He brought out a Bible, and read some of it to me, too.

So, I find out he had no transportation plans so whatever, I shared a car with siblings, and was able to use it, so I drove us to the arcade. He increasingly got frustrated he couldn't "kick my butt," even though every game we played, he never played and, like I said, I frequented the arcade so I was well-versed with them. He also didn't realize I knew how to play pool.

I’m really bad at it, but was better than him. Played some old fashioned arcade games, and won some tickets. I hate ticket prizes, so told him to give the tickets to a kid. Instead, he got me some crummy bear. He also told me he didn't wash clothes, but just bought new shirts when things were dirty. I told him I was ready to go home at around 11 PM—I never gave up an opportunity to hang out at the arcade, after all—and I would drive him home.

Turns out, his family disowned him, and he had been living in an Econo Lodge hotel for the last six months. I tried to avoid his calls, and then he started calling from a different phone number. I told him I didn't want to go out again, and then three years later I thought it'd be funny to login into Myspace, and he had messaged me recently there saying we should try again.

Worst First Date FactsShutterstock

18. Bad Date Topics

We had our flight canceled due to a snowstorm on Christmas Eve. The only place open for dinner was an Indian restaurant. There were a few customers in there. It was an interesting looking bunch, sort of what you'd expect eating out on Christmas Eve. This one couple though looked to be in their 40s. A guy and a woman.

She never said a word and looked like she was in a trance. The guy though kept talking at her in this slow monotone: "And another thing I hate about you," and proceeded to critique her while she continued to stare into space.

I’m Outta Here FactsShutterstock

19. Gone in 60 Seconds

A girl and guy came into the barbecue restaurant I worked at. They met at the door exchanging the usual, "Hi, nice to meet you!" pleasantries. The guy was a complete jerk. She ordered ribs, and he said, "Do you want to keep that hot figure of yours or look like that chick over there?" while pointing at a slightly overweight woman nearby.

Then, when they were waiting to pay, he starts flirting with the chick behind them. She waited until he paid then left without waiting for the food. At my work you ordered, then paid, then the food was brought to you. So she left before the date even really started.

Worst First Date FactsShutterstock

20. A Lively Woman

A friend and I meet up and 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.

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21. Over the Top

The dude was waiting in the parking lot, singing and playing guitar when she arrived. He was dressed VERY formally—except for his sandals. They ate and drank. He got up and squeezed in next to her on her side of the booth. She was trapped. She looked mortified the whole time. The whole thing was completely cringe-worthy.

Worst First Date FactsShutterstock

22. 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.

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23. Mommy Dearest

I work at a bubble tea restaurant right near a college. It's a nice hangout spot with dim lighting, comfortable furniture, and board games. 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. 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.

Worst First Date FactsShutterstock

24. Don’t Be Cruel

I worked for IHOP for a very long three months. Most of my experiences were decent. On one occasion, one of my acquaintances came in with a date. We had been friends as kids, and still sometimes chatted amicably. At this time, I had a stutter that would happen if I spoke too quickly, was stressed, or just trying to speak hard words.

I went up to their table, said hi to my friend and her date, and instantly flubbed the greeting with a stutter. Honestly, my stutter has never bothered me, never felt like a bad thing until that moment. Her date looked at me, did that little condescending laugh that we've all heard before, and then repeated what I said while mocking my stutter.

I could see my friend physically recoil from him, her face clearing showing a "did you really just act that way?" expression. At the time, I just brushed it off. It bothered me for about two seconds in the moment, but even years later I still haven't forgotten. Still, I could tell with that one little moment of acting like a jerk, my friend was not going to go on a second date with him.

Cringeworthy Dates factsPxHere

25. Don’t Order for the Lady

I witnessed the "shortest date" once. I immediately knew it was a first date because I'd greeted the lady, and directed her to the bar while she waited for her date to arrive, and then saw them introducing themselves when he finally showed up. They ended up in my section, her with an almost empty martini, him still drink-less.

It looked like the small talk was going somewhat well. Normal first approach, good evening, blah blah, what can I get you to drink sir. He orders a Jack and Coke or something similar, I can't remember exactly, and I ask the lady if I can get her another. Before she has a chance to answer, the guy interrupts, and says water will be fine for her.

Normally, I'd ignore a comment like that, or pretend like I didn't understand and ask her directly again, but didn't even have a chance. She went off on him, "How dare you," etc. etc. She stood up, apologized to the small dining room and to me, and walked out. Though clearly embarrassed, and speechless, the guy stayed and continued to order dinner for himself anyway.

Super awkward. Tipped me well though if I remember correctly.

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26. Wine About It

I worked as a waitress in an Italian restaurant while attending university in 2006. An obvious first date comes in. He's booked it and requested a table in a secluded area of the restaurant because the acoustics would be perfect. She arrives and asks to move to a table to by the window. No big deal, but he's annoyed at this.

They ordered a carafe of the house red with their meals. Anything she said, he'd turn it into some achievement he'd already accomplished. He kept making comments about her order, such as how fattening a dish would be, and then proceeded to say his family owned a vineyard, and he knew a good red wine when he smelt one.

He then asked for the most expensive vintage on the menu, and to take away the what he called, "poor house wine" then talked about how the bouquet was different, and the clarity was so much better on the "expensive" vintage. When it came to dessert, she had enough of his nonsense and flipped when he said that she shouldn't have any, or she'd end up with stretch marks.

She was a bit overweight, but not overly so. She stood up and yelled at him for being a condescending piece of filth, for knowing fudge all about wine, and dropped the coup de grâce that her father was our supplier and that the house red was exactly the same as the most expensive vintage—all of which was totally true.

He was left speechless with the full check to pay.

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27.  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 booze—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 harass me into getting some booze, 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. She told me he goes there every other weekend with a new girl, and that the girls would walk out of there acting very intoxicated, 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 gets girls inebriated to sleep with him via pressure tactics. 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.

Worst First Date FactsShutterstock

28. Last Date

Not a first date, but the last date of a 50-year marriage. The guy literally confessed to cheating on his wife while they were sitting at my bar in the middle of a busy shift. Needless to say, she didn’t give a flip about causing a scene.

Cringeworthy Dates factsGetty Images

29. Whacky Tobacky

This is a story of my worst first date. I helped out a guy with a film project. Nothing fancy, just helped with lighting. He was quiet and awkward, but I thought it was kind of cute, so when he asked me out I agreed. He picked me up at my dorm, and told me he decided we shouldn't go out to eat, but drive around doing weed.

I told him I didn’t want to that, but he ignored me and continued to smoke a pipe while driving. He became more odd and erratic the more he smoked. He was laughing hysterically at nothing, yelling inaudibly—it was unlike anything I've ever seen weed do to someone. I finally demanded to be let out when he started driving up on sidewalks for fun.

I tried to get out at a stoplight, but he gunned it, and sped through before I could open the door. I seriously thought of doing a tuck and roll on the pavement. Finally, he agreed to take me home, the entire time telling me how boring I was, and how he didn't realize I was such a snob. He pulled into a parking lot on the opposite side of campus and asked if I wanted to make out.

I just got out of the truck and hoofed it to my dorm.

Couple arguing about something in a car.Getty Images

30. Double Trouble

I sat next to one heck of an awkward first date. It seemed there was an older couple setting up two younger people, and the four of them were on a double date. Anyway, the young guy was a complete jerk. I distinctly remember him telling a drawn out story about his shirt, and how it had square buttons, and they were better for some reason.

And he bought it at this exclusive place for men, where they have hot women come and fit you for clothes. The rest of his stories were similar, and he did most of the talking. The older woman was enthralled by the young guy's stories. The older guy, and the young woman seemed annoyed out of their minds.

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31. Missing Information

When I was a host at a restaurant, I sat a couple in their mid-40s at the bar. Their server was my roommate, and she comes up to me, saying how weird they were, same-siding, making out at the table, etc. A few minutes later, an angry-looking man comes storming into the restaurant, and stands at the host stand just looking around.

I asked him if he needs a table, and he gives me an icy glare, and then marches over to the couple in the bar and sits down opposite of them, the woman looks horrified. The angry guy is whisper-yelling at the woman, all I could make out was that she was on a date with a man she works with and the angry guy was her husband, who found out through another friend.

Now, I'm just standing at the host stand, five feet away, watching all this go down. I grab another server walking past me and tell them what's going on. The husband at the bar starts getting louder, so my roommate gets the biggest cook we had, and had him go to the table, and tell them to leave. The woman and husband leave, leaving the other man there just looking confused.

He sits there for a few minutes, just kind of staring down at all the uneaten food, before getting up, and coming to the host stand to ask for his bill. I go get my roommate so she can print the check, when I come back, he pays and just says, "I'm sorry for the disturbance, I didn’t know she was married," and leaves. I felt so bad for the poor guy.

He seemed very into her up until her husband showed up.

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32. Two’s Company Three’s a Scene

One time I had two women arrive together. I figured they were just out for drinks. They requested a special table with a window looking out to the bar. Whatever. They're seated there, and I serve them drinks when suddenly 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.

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33. Dessert Storm

I work at a cafe where we make cakes, sundaes, etc. It was a Friday evening, not to mention Valentine’s day was around the corner, so we get the usual busy crowd of couples, and dates coming in for some desserts after dinner. I was bringing some food to the tables when I noticed a couple come in. A woman dressed in a black dress, her hair done up all nice, and fancy makeup, looking absolutely furious.

She's followed by a guy, dressed super casually, on his phone, and isn't paying attention to where he's going. Stopping every few minutes to text. The girl makes her order, and every time she orders something, she looks angrily at the guy, who just looks at his phone. Me and the cashier share a confused look at each other.

She must have ordered about 10 things, and then went to go to her seat. I prepare the slices of cakes, and bowls of ice cream, and look over at their table everyone once in a while. The guy is slouching in his chair, still on his phone, and the girl is looking across the table at him with the glare of death. I bring them their cakes.

As I set down the tray, the guy finally looks up from his phone. He opens his mouth to say something, then just goes back to staring at his phone. I walk away, but when I get back to the counter, the cashier put a hand on my shoulder, and points over to the couple. I look back to see the woman gobbling down all the pieces of cake.

She's ignoring the provided silverware, and I don't even think she took a moment to breath. I had never seen anyone devourer so many pieces of cake like it before in my life. The guy is watching with as much shock as us. My guess is the woman snapped, and began to give zero cares anymore. She walked to the counter with chocolate and cheesecake smeared on her face, looked at the cashier with crazy eyes, and slapped a $50 bill onto the counter.

She left in a hurry, and the guy sat there for what felt forever, with his phone down. Weirdest shift yet.

Worst First Date FactsGetty Images

34. Have Dinner or Else

I tended bar at a country club. I worked the busy league nights. One night, it was late and there was still a straggler that said his group left him behind and asked me for a ride home. Being young and naive I agreed. The address he gave me directions to was a restaurant—back then I had a Blackberry and cellphone GPS was still a very young technology.

When we arrived, I was irate. He said he wouldn’t give me the address for his home until I had dinner with him. I feigned getting out of my car so he would get out before me, and then sped off, leaving him standing in the parking lot alone. He really thought he could blackmail me into a first date.

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35.  Luck or Skill

I was on a first date, and we were comparing extra-curricular activities. He was in a bowling league and played softball. I was on a dart league and played volleyball. We were talking about darts and whether it was or wasn't an activity that demanded some sort of skill over luck. I felt a bit insulted by his patronizing attitude, and before our food even came we started to argue across the rather large booth where we sat.

He said, "FINE, since you're so skilled at darts, see if you can get an ice cube into my mouth from there," and I said, "FINE, open up!" He opened his mouth, and I totally just launched an ice cube straight into the back of his throat. His eyes bulged and he clamped his mouth shut, grabbed his throat, and fell over in the seat.

This waitress that had been standing nearby, shaking her head at our stupid argument, ran over to help when, he sat up, threw the ice cube onto the table, yelled, "SCREW YOU!" and stomped out. I said that I was really sorry, that I didn't mean to get it into his throat, blah blah, but he kept on stomping and I never saw him again.

Sometimes it's better to be lucky than good.

Worst First Date FactsPexels

36. Wrecking Someone Else’s Date

I was 18 years old, and my date and I went to a small café. Not the most glamorous date, but he and I had known each other a while, and both agreed we wanted somewhere pretty basic. As we were talking I noticed this older woman across from us giving us nasty looks—if looks could kill I would have been gone 10 years ago.

She was talking to her husband, who was obviously trying to get her to quiet down—keep in mind, we're two guys on a date in the conservative South. Now at this point, my date hasn’t noticed her, and I haven’t said anything. I get up to use the restroom, and this lady gets up, grabs my arm, and starts mouthing off about how inappropriate it is to be acting this way with someone of the same gender.

She’s spouting off a bunch of bible-thumping garbage. I look at my date, and he is super bewildered. The husband grabs his wife's arm and says, "Go get in the car, we're leaving". He escorts her out the door. The husband actually came back, and apologized before offering to cover our bill—we declined, but appreciated the gesture.

Parent-Teacher Conference FactsShutterstock

37. 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.

Worst First Date FactsShutterstock

38. Pay Your Way Out

I was new to the DC area, and being so new to the area, met a girl from a craigslist ad. She seemed nice, we had some common interests, and talked for a bit and decided to get coffee, which then led to a movie, and a dinner date. She wanted to invite her best friend and her friend’s boyfriend, and do a double date—that was fine.

But come date time, the guy was "busy" with work, so her friend was the third wheel. We had coffee, I paid for all three of us, then the movie, I paid for all three of us, which was not a problem for me. After the movie, we move towards dinner, and her friend's boyfriend has finally showed up, so I think, "that's cool".

We go to dinner, and all he talks about is his job, all she and her friend talk about is his job. He works IT for the government, I work IT for a private company, we exchange banter about IT, but the girls keep talking about how much money he makes working IT for the government, and I am just done with this line of conversation.

They are all comparing me to him. Whatever, I maintain a nice demeanor, but am not having a good time since every topic revolves around him. When it comes time to part ways, I ask the server for the check. It's just a little over $100, and I want to leave. She asks how to split it, I said don't bother, I got it. Then comes the gentlemen fight.

Dude who was talked up throughout the meal wants to pay, I said I got it, he insists since he missed the coffee and a movie, I insist back—mostly because I wanted out, and wouldn’t chat before placing my card down. He further insisted. I just said fine. Later that night, the girl, who was otherwise nice until her friend and friend’s boyfriend showed up sends me an upset message about why did I let him pay, etc. I had a steak, etc. So did he!

Rich Kid Syndrome FactsShutterstock

39. Should Have Stayed Home

My date said that she had been sick but was looking forward to getting out of the house. So we went out to a restaurant, and somehow the smell of the salad bar made her go to the bathroom and vomit. Like, drop her water glass on the floor where it shattered, and drop her purse on a table full of people on the way to the bathroom, and then you could hear her vomiting. Yeah, she was sick, I guess. And then she was so embarrassed that she would not talk to me afterward. The worst part? She was HOT, gosh darn it!

Worst First Date FactsShutterstock

40. 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.

Worst First Date FactsPixabay

41. Make a Run for It

There was a couple sitting at the bar, very clearly on a first date. About 20 minutes later, I was back in the kitchen rolling silverware, and the guy comes running back into the kitchen and says, "Is there an exit back here?!" Didn’t wait for a response, saw the exit sign, and bolted out the back door.

Cringeworthy Dates factsMax Pixel

42.  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.

Worst Airplane Experience FactsShutterstock


Sources: Reddit,

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