Sometimes first dates go well, but usually, it's not that easy. And once in a while, they totally go up in flames. These dating disasters are often the worst case scenarios in each situation. In some cases, it's the couple's first time meeting each other, but others just aren't meant to be, even if they are together. Check out these terrible dates. Content has been edited for clarity.
Never Say THIS About A Woman’s Kid
“A man and woman, probably in their 30s, were having a dinner date. She’s talking about her ex-husband and he doesn’t sound like the best of guys.
Then this idiot chimes in, ‘Well, you both made mistakes it seems.’
‘What do you mean?’
‘Well, him for all the things he’s done and you for having kids with him.’
She was ANGRY, not screaming, but she quickly grabbed her things, gave him a few choice words, and was gone in 60 seconds. He sat there with a ‘what did I say?’ expression and paid the bill a few minutes later.
Don’t call someone’s kid a mistake. It’s not going to end well.”
Trapped In A Relationship
Shutterstock / Mladen Mitrinovic
“An Eastern European couple walks in. She looked like she had been crying, but they ordered and seemed nice enough. A few minutes later, I heard a commotion going on in my section. I got there in time to see this man reach over and slap the woman hard enough that the whole lounge heard the sound. He looked like he was gearing up to hit her again, so I instinctively stepped in. I was and am a small, petite woman with no martial arts training or anything and told him to back off and leave or the cops would be waking him out. Surprisingly, he just left without a fight. What was disturbing is that the woman very quickly composed herself and by the time I went over to check on her (seconds later) she was brushing it off like it was an everyday event. I guess it was for her.
I told her I would feel better if she stayed in the lounge for a bit so we could be sure the man was gone. She agreed and I got her a few drinks on the house. Once she was a little more opened up from the drinks, she told me her story, about how this man brought her to the US and that she was afraid if she left him, she would end up being forced to go back home. She also warned me never to date an Eastern European man and that most of them were like that. I wanted to take her to the police or to a women’s shelter, but she refused and wandered out into the night. I never saw her again, but I hope she is okay and away from that man.”
“Fon” Don’t Do It!
“I worked at a fondue place. It was usually a 1.5-2 hour meal for two people. We served a full four courses, the works.
A couple came in and he had pre-arranged with us to present an engagement ring with the chocolate course with melted chocolate on the plate spelling ‘Will you marry me?’ Also roses and other embellishments on the plate.
Apparently, the entire meal she was explaining to him how bad he was at being in a relationship. Too needy, too emotional, somehow he also didn’t spend enough time with her and wasn’t connecting with her? It was an hour-long breakup speech.
We come around the corner with candles lit and the chocolate fondue and the engagement ring on the plate, the table next to them did everything they could to wave us off, I was holding a camera to capture the magical moment, which obviously never came. He tried to get his prepared remarks out, but it was so bad, we eventually left the dessert at the table and tried to act like nothing had happened. She left before the check came.”
A Disaster Of A Proposal
“I work at a dinner theatre and we usually do proposals where we set up a ‘random draw’ where the ‘winner’ comes up on the stage to win their prize, and are then surprised by their partner who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm.
This one guy wanted to take it further and requested to perform a song — he brought his own music and everything. We’re pretty easy going at this job, so we agree to let him do it.
We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently, this guy was a little nervous and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy, that seemed to focus on how he was sorry for cheating on this woman with her sister and at the end of it, he gets down on one knee and proposes.
Usually, this gets a round of applause, encouraging the person to say yes; but not after that trainwreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says, ‘No, what’s wrong with you?’ She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience.
The only thing our stage manager can think of to say on the mic is, ‘Well, that’s that.’
The guy ended up staying for the rest of the show and had many more drinks. That was years ago and it still remains one of the cringiest things I’ve ever seen.”
A Work Relationship Gone Sour
Shutterstock / CREATISTA
“This man and woman came in and the first thing I notice is that the woman was noticeably older than the man but I don’t really judge about that kind of thing. I also don’t assume people are on dates. Maybe she is his aunt? Or they are just friends?
So I went to go ask about drinks and do the usual peppy greeting and she is super chatty. Basically, she talks for him and answers questions that were straight for him. Okay, I think, maybe that’s just how they are. Whatever. She proceeds to order them both heavy drinks straight..at 10 am. I figure, ‘Eh, maybe they are on a vacation together.’ You never know.
It finally hit me that something wasn’t right was when she wouldn’t stop making inappropriate comments about the two, which is how I knew it was kind of a date. I am talking straight up things like, ‘I am 53 but with the amount of work I have had done to my downstairs, he won’t be able to tell tonight if I am actually 23.’ I am watching the man’s face and he looks pained.
I watch the table from afar. I realize it kind of looks like a date gone wrong, but they seemed to know each other so I am not really sure what is going on (and servers always chat and theorize about their customers in their free-time), when the man gets up and comes over to me and asks me to chat with him around the corner really discretely. So I do. He looks like me and is talking super fast as he explains that this is his boss and he has to meet with her quarterly and she just has to sign a single form to approve what he has been doing and she insists on going out for a meal and drinking and then trying to sleep with him. Every time.
I was horrified for him– he looked that panicked. He said that he usually gets her to sign it before they leave the restaurant and then makes an excuse to ditch her. We made a code sign (him patting the back of his head three times) so that I could intervene when she would get far too inappropriate but honestly, she didn’t change much when I would come. He also asked me to bring him fake adult beverages, said I could charge full price for them for but to make them water or just soda.
I still think about him sometimes and wish I had gotten his name or something so I could check in and encourage him to report her, but in all honesty, she probably owned the company he worked for or something the way she spent money and looked.”
No One Could Have Predicted That
“I work at a Red Lobster. One time I was serving a table of two who had clearly met up for a first or second date. Both of them seemed very wealthy, but the gentleman specifically seemed a little odd.
Long story short…the gentlemen began coughing and went to the restroom for a second to get himself together, but ended up taking around 30 minutes. The lady requested we go in and look for him, so we did. It turns out he had a massive heart attack and we found him dead on the bathroom floor. We didn’t quite know how to tell the lady, or even what to do really (besides calling the police), but by the time we went to look for her, she had taken all of his things and she had left. Not so much awkward as much as just a weird, messed up scenario.”
A Quiet Fight
Shutterstock / Roman Kosolapov
“I served a deaf couple having a fight. They went from both of them signing furiously to her crying and signaling to me for a stack of napkins for, I assumed, her tears. She whips out a pen and starts writing paragraph after paragraph angrily. She would sign, stop, wipe some tears, start to sign, cry some more..so I’m assuming she got her thoughts out better in writing rather than signing to her guy.
I walked backward after the fight got into earnest into the kitchen and my coworkers were hysterical laughing when I told them why. My boss said ‘At least it’s a quiet fight. Keep an eye on them to make sure they don’t start throwing things at each other.’
It was awkward because I kept having to come back to the table since they ordered multiple courses and he was just eating and signing while she was hunched over the table writing away while crying. When they finally left, they tipped me pretty well though, so I guess it wasn’t too bad?”
Served More Than Dinner
“I was working at a vino bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered. Once appetizers came out, the man thought it would be a good idea to serve his wife divorce papers. I did my best to avoid that side of the bar. I did bring out tissues for the wife who was breaking down.
My only guess as to why he brought her out to dinner was that the wife was prone to overreacting. Overreacting in the sense that she would throw things or hit. That was my mind justifying the situation though.
I ended up boxing up the dinner. The guy paid but I do not envy that ride home.”
A Bad Match
“I was at one of these fancy, speakeasy-type establishments they’ve started opening up, installing a new invoice printer for their Point of Sale system. Waiting for the printer firmware and driver to install can take 30 or 40 minutes on slower computers, so I was people-watching.
As I’m standing there watching the bar fill up, I notice a gorgeous blonde in her late 20s is sitting with a very well-manicured looking guy in his mid-40s. He’s dressed like he just left a high dollar law firm and she looks like she’s going to a fancy professional party after their date. He is polite, talkative, and super into her, but you can tell that she isn’t reciprocating the feelings. To be honest, by the look on her face, she wants to be anywhere but in that bar at the moment.
The guy goes to the bathroom and she quickly picks up her phone and frantically calls someone and begs for pickup ASAP. The gist of the call was the guy was her mother’s coworker and her mother had set the date up, and our girl really wasn’t feeling it. About fifteen minutes later, a guy around her age comes in, throws some cash on the table and excuses them. She cites some vague emergency and is escorted out.
The older guy continues drinking ($140 tab, note that I’m standing at their main cash register) and starts flirting with the waitress, fails to get her number, pays in exact change without tipping, and leaves.”
Not Again…
“I worked in a resort hotel, high end, I waited tables in the fine dining restaurant. It was pretty common for people to propose there, so much so that I had a system for the whole thing. One guy came in and wanted to do the ring in the glass thing, and I talked him into doing a dessert alternative that doesn’t result in a sticky ring and bubbly on the floor.
I bring the ring, she says, ‘I’ve told you before I’m not marrying you.’ He flips, she’s super calm about it and basically treats him like a child having a tantrum, which to his credit he was not screaming or anything, just very upset. He left, she ate the dessert and eventually, he came back and paid and they left together. Super awkward.”
The Worst First Date
Shutterstock / Antonio Guillem
“Okay, so I was working at P.F. Chang’s at the time. In my opinion, it’s sort of an odd place to come on a first date but maybe that’s just me.
So they sit down and order drinks, he got a mojito and she got the Japanese Old Fashioned which is basically just straight up, so good start. They’re maybe like late 20’s or early 30’s.
Everything is going fine while they wait for food, they’re table was right next to the ordering terminal, and I’m kinda chilling by it because it’s slow. I realize by the conversation that it’s a first date. They were saying things like ‘oh, do you have any brothers or sisters?’ and ‘Where’d you grow up?’ That kinda thing.
Their food is kind of taking a while, so I stop by to make sure everything was okay, and she’s now on her second old fashioned and I noticed she is pretty red in the face, and slurring like an idiot, but I thought it was weird after two.
I went and told my manager, I thought she might have brought her own stuff in and was drinking it when I wasn’t watching. He said to stop serving her and keep an eye on it.
The dude gets up to go to the bathroom as I am walking by the table and she stops me and asks how much longer the food will be, slurring badly. I tell her a couple more minutes and start to walk away and then she stops me and she’s like, ‘you’re really pretty you know that?’ I was like, ‘oh thank you I’m flattered.’ And she like won’t let it drop, keeps telling me I should model, maybe for upwards of 2 minutes. I was extremely uncomfortable, and it was at then this point she asks, ‘do you think my date is attractive?’
I was like OH BOY HOW DO I ANSWER THIS? So stupid as I am clearly struggling on how to answer this she says, ‘I can tell you’re flirting with him.’
At this point, I didn’t know what to say because I wasn’t flirting, I was just doing waitress things so I just said: ‘I have a boyfriend.’ And walked away. Now, I am avoiding walking by the table at all costs.
When I bring the food over, the girl is literally crying. I have no idea what happened in between the time I left and when I brought the food over. The poor dude who has literally had one drink and looks horrified asks her what is wrong while I am standing at the table, and she picks up her head, GLARES AT ME, and goes ‘HER.’
He seems confused and I walked away but I heard her getting more hysterical as I did, I walk into the back and start cracking up at this woman and I send my manager out there to see what’s going on. He comes back and said that the dude said everything was fine with the meal and service. When I walk back outside the kitchen to check on my other table the dude is standing at the door waiting for me and I’m like, ‘oh no.’
He shoves his credit card into my hand and goes ‘can you please just swipe this and call her a cab I need to leave,’ and he’s apologizing profusely and saying how he doesn’t know her and it’s a first date; I assure him I am fine. I swipe the dude’s card have him sign the receipt and he leaves.
Now I’m just completely ignoring the table because there is way too much weird stuff going on over there but still watching the woman. And I notice the woman start to look around towards the bathroom, she’s still crying. The guy had maybe left like five minutes ago. And I realized he didn’t tell her that he was leaving, he just paid and left. 10 more minutes go by and I think she realized he just left too. I hid in the kitchen until she eventually left. I still have no clue what went on at that table, but I’m glad that guy got the heck outta there when he did.
The hostess called her a cab because he drove.”
Can’t Even Get It Right At McD’s
“I worked at McDonald’s (one of the thankfully less trashy ones) and a couple came in. The woman sat down and the man tried to order. There was lots of umming and ahhing at what he wanted to buy, and he eventually ordered two meals that we gave to him and he went and sat down.
What followed was a 10-minute shouting match about how he wouldn’t take her on a ‘proper date’ and how he messed up even a McDonald’s date. I guess he ordered the wrong thing.”
The Scariest Glare
Shutterstock / KannaA
“This couple sat at a table with two crying children. I walked up and said, ‘How are you doing tonight, what can I get you started with to drink?’
The father said, ‘Do you have anything back there that I can blow my head off with?’
The wife’s glare at him was the scariest thing I’ve ever seen; I honestly hope that man is still living.”
Too Romantic Too Soon?
“I was working at a local Mexican restaurant. This guy came in saying he was going to be meeting a date. She was coming a little later. He asked for a more private spot, which wasn’t hard to do. It was like 9 pm and we were almost empty.
So the server sat them at a small booth in the back room. He was telling her how it was a special date or something. It was a couple weeks before Valentine’s Day and we had some candles so she lit one for them and put it on their table. He had also brought in some roses and a vase for the table. He was showing her this necklace he had bought and was going to give to the woman.
So this woman shows up and sees this whole set up and looks super uncomfortable. This guy was trying to physically put the necklace on her and she refused to take it. It was apparently only their second date and this woman was freaked out and ended up leaving.”
Blind Date Fail
“This was just before Tinder and dating apps were a thing. It was a blind date, guy and girl. Guy shows up first and is excited until he sees his date. She had their mutual friend show him an old photo of her because she had since gained significant weight.
You can tell he was let down but decided to make the most of it. They order drinks and appetizers. We didn’t even get appetizers out before the guy noped out of the date. He sat at the bar asking us to bring the appetizers to him there. Her weight wasn’t the only thing he was lied to about. Her personality and his clashed so hard that the date didn’t last 10 minutes. He hung out well after she left. We (the bar and wait staff) invited him to hang out with us at a bar after work. He ended up being a cool guy.”
Poor Average “Joe”
“When I was bartending, this guy came into the bar on a weeknight, average looking guy, late twenties. He sat down and asked for a drink and told me he was nervous because it was his first date in three years and they had met on Tinder. He arrived 20 minutes before her expected arrival to get rid of some of his nerves…two hours passed and he waited for her with no text or call explaining she would be late.
This woman walks in, walks up to the guy and I’m thinking, wow! She really came! She looks at him and says, ‘Are you Joe?’ The guy replies yes and gets up to properly greet her looking incredibly excited. She says, ‘No, thanks…’ and just leaves.
What a foul creature. Joe (not his real name) and I proceeded to get way too wasted for a Tuesday. Poor, average Joe.”
