Dating is awkward, let’s just face it. At first, it’s hard to find your footing. Then one person may fall harder than the other. Then maybe an ex gets involved. Then, then, then..!
And where does one draw the line from “We’re just getting to know each other” to “We’re a full-blown couple”? How fast should things move, anyway? You might assume things are exclusive with that hot hunk or pretty lady you’ve been on a handful of dates with, only to realize that they’re still dating multiple people or, worse, married! Or, maybe your so-called boyfriend or girlfriend suddenly lets you know that they’re not really into you and that you’ve basically been going on dates with a “pal” the entire time. And a common problem these days are people looking for a quick hook up, thinking that a fancy dinner will land you some intimate time meanwhile, you’re looking for an actual relationship. It’s tough.
And just to make things more interesting, while you’re on your first blind date or date #6, you’re probably doing it in a public setting, out at a restaurant or at an upscale watering hole. Basically, you always have an audience! All the servers, tenders, cashiers, hostesses, manager and more actually pay more attention than you think.
Plus, if it’s a slow night? Guaranteed the staff will be eyeing and analyzing how cringy your date is!
First dates, in particular, can be pretty wild. Things can go right or go South really quickly, but since worst first date stories are always more entertaining, we’ve compiled a collection of some of the craziest, scariest, lamest, and most messed-up dates real people have actually gone on, as witnessed and told by restaurant workers.
30. The DJ Baited Several Men With A Fake Date
“I used to work at a wine lounge, where they would regularly book DJs and host events to bring in a younger nightlife crowd.
This one night, we had a French DJ playing, and as the night went on, I started to notice several men sitting by themselves. None of them were engaging each other, and a few told me they were waiting for someone. As the night went on, it got to be something like 8 to 10 men, all sitting alone. I started to ask some of them if they were waiting for a date. One man said yes, another said no, and then left right after. Kind of weird… I felt like something was up with the situation.
After about 45 minutes goes by, I see two of the men start to talk. I see they are sharing something on their phones, and I engage them in conversation. They then tell me that they realized they were waiting for a date…and had a picture of the same French, middle-aged woman from the same phone number on their phones. Then it clicked – all of these guys were being baited by a fake person to come meet them!
Eventually, all of them ended up outside talking and trying to figure out what on earth was going on. Most of them leave, and the two guys I originally talked with ended up staying and hanging out together.
They thought it was hilarious!
Then it dawned on me: the date. At midnight that day, it was April 1st. Someone pulled a major dating prank on all of these poor unsuspecting guys. And later on, when the DJ came down, I told him about what happened, and then I asked him if he knew what was going on. He didn’t say yes or no; he just kind of smiled and had a strange look on his face. Then I realized that this DJ had to of been in on it.
I think he set up a fake online dating account of this woman, baited a bunch of single guys to come out and pay the door price to get them into his show.” Source
29. He Pooped His Pants In Front Of Everyone, Including His Date
“So, I used to work at a place that was well known for its wings (not BWW). I had, what was obviously a Tinder date, 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, things can take a turn for the worse.
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. Tears were streaming down his face, so I got him some milk. I think we are 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 restaurant. 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 soiled his pants. To be fair, they were really nice kicks.” Source
28. He Was “Perfect” And Judged Anyone Who Wasn’t
“I was sitting next to a train wreck of a date at a nice restaurant once.
The guy was very into himself, kept describing how awesome he was to a woman who very clearly did not want to be there. She kept looking around with eyes that screamed, ‘Someone, please just get me outta here.’
She ordered a second drink, probably to cope with the insanity, and the guy says to her, ‘Oh, you like to drink a lot, huh? I’m not a huge drinker, but I guess that’s okay if you are.’
Fast forward to when they were finishing their meal.
She was eating her food, he kept talking about how wonderful he was when he paused for a second and asked her, ‘Do you always feel the need to eat everything on your plate? That’s really unhealthy, you know. You don’t want to do that every time you go out to eat, or you’ll wind up getting fat, and fat wouldn’t look good on you.’
She sat there, shocked, not responding, and then the guy just continues, ‘Well, anyway…’ talking about how amazing he is and does all the coolest things.
After they left, I said to our waitress how sorry I felt for the other woman. The waitress winds up telling me ‘Oh, yeah. Dave is a regular here. He brings in a new date every week trying to impress them, but none of them seem too happy, and he’s had a few just walk out.'” HoneyBadgerKev
27. He Matched With Her Best Friend While They Were In The Middle Of A Date
“UK waiter here. I was a head-waiter at a very nice steak restaurant about a year ago. We were pushing 180 to 190 people a night into this 50 seater restaurant.
One night around May/June, a server came up to me and asked me to take over a situation that has been developing in her part of the restaurant.
As soon as the words left her mouth, I heard shouting and swearing.
Rewind 20 to 25 minutes beforehand. Lovely couple (we thought they were a couple but they weren’t, they were dating) that I sat down in our ‘nice’ seats we reserve for couples. They were being all lovely and cute, making small talk, and the lady went to the toilet after they ordered their food.
Apparently it took her a few minutes more than usual to come back, and she came like a storm.
Screaming and shouting whilst still being considerate to others around her. The waitress tried to calm her down and asked her if she wanted to go and calm down outside, but the girl was having none of it.
Turns out, while the girl was at the toilet, the guy had matched with some girl on Tinder that unbeknownst to the guy just happened to be the girl’s best friend. And he was messaging the girl saying how bad of a date it was and how the girl wasn’t what she said she looked like online, and how she had no ‘craic’ (meaning she isn’t very talkative and boring).
And while the girl was using the restroom, her friend told her all of this!
In hindsight, it was all very funny, but at the time, it was rather annoying.” ozirakhan
26. He Thought Eating A Wad Of Wasabi Would Impress Her
“About a year ago, I was a server at a sushi hibachi grill restaurant.
I witnessed a plethora of awkward and uncomfortable first dates, but one in particular sticks out in my mind.
It was a young couple, early twenties, I would guess. The date started out with a lot of formal and shallow conversations along with a lot of awkward fumbles. You could tell the girl was a little disinterested and started looking around impatiently.
Then when I brought them their food, the guy made a comment about how I was a caucasian female working at a Japanese restaurant. This really didn’t sit well with her, making things even more uncomfortable.
When I walked by about 10 minutes later, I saw that he had compiled the wasabi from both his and her plates and decided to eat it in one mouthful in hopes of impressing her. About five seconds after swallowing, he started crying and gagging while she just made a face of pure disgust. He got up to run to the bathroom with his hand covering his mouth with vomit shooting through his fingers and onto the floor on the way because he couldn’t keep it down.
She promptly left the restaurant. It was pretty darn awkward.” Earth2Julia
25. The Mountain Of Cheese On Her Pasta Turned Him Off
Girl loves her cheese!
“Was waiting on this couple, who are clearly on a first date.
The man seems initially delighted with her. I take their order and she orders the fettuccine alfredo. Cool, no problem.
I bring their orders out, and as it is custom at our restaurant, I ask the lady if she would like some freshly grated parmesan on her pasta. She goes, ‘Oh yeah. I looooove cheese. Your arm is going to get tired. I’m warning you!’ Her date smiles at her, clearly thinking she’s adorable.
Now I’ve heard this and dealt with this before. I have grated a lot of cheese in my serving career. It’s never been a problem and I almost never judge someone’s cheese preference, being a dairy lover myself.
I will never forget this lady. I have never grated that much cheese before or since. It starts off normal, and her date is still smiling at her. The pile begins to grow, and he chuckles, clearly thinking this is some cute quirk.
But she doesn’t tell me to stop. You can no longer see any pasta on this dish, and our dinner pasta portions are very, very large.
I can see on his face that his initial delight with her is slowly morphing into surprise. The smile is growing smaller and tighter and his eyebrows are going higher.
And, still, she doesn’t tell me to stop. She’s clearly thrilled and obviously wants MORE cheese grated on this thing. For the first time, my arms and wrists start to hurt. Now there is nowhere left for the cheese to go but UP. A small humped mountain of parmesan is growing on this woman’s plate. FINALLY, after what seems an eternity, she says, ‘OK! That looks great!’
I am not exaggerating when I say she was having some pasta with her cheese.
I had to get a fresh block because it was worn to the nub. My wrists hurt like hell, a first for cheese grating in 8 years. This dish looks absolutely gross. I look over at the guy’s face, and it has now morphed again from surprise to pure disgust and embarrassment.
She is completely oblivious and digs into her cheese stack still chirping and chattering at him, and he won’t even make eye contact anymore. The smile is gone. He is clearly over it. It’s very obvious there is not going to be a second date.
I skip asking if they want dessert and bring him the bill as quickly as I can without appearing to rush them.
He gives me a look that all but screams, ‘Thank You!’ and makes his excuses to go, leaving me a VERY nice tip for expediting this painful experience as much as was professionally possible.
Haven’t seen either of them back since.” fairywings789
24. His Mom Showed Up And Berated Him For Dating Someone Of The Same Gender
“I own a bakery with a storefront/cafe, I see a lot of first coffee dates fail and crappy people in general, but there’s one that will always be the worst for me. This happened at my bakery maybe six months into our first year.
Two boys come in, clearly nervous, and on what has to be their first date together and maybe their first date, period.
They’re both young, maybe 15 at most. They order at the counter and go find a table. I bring their stuff around, and they’re both giggling over something, blushing, just straight up adorable. One of them starts holding the other’s hand, playing with his fingers, and they both go quiet, eating with their opposite hands, and then giggling more.
My only other customers were this group of maybe six teenage boys hanging out in back of the store, so I’m watching this sweet interaction like it’s the most adorable of nature documentaries about teenage boyfriends in the wild.
All of a sudden, this woman comes in and starts looking around the store for something.
Before I can open my mouth to ask or say anything, her face instantly drains of color, and she marches right up to them and starts berating one of the boys.
Over the next few minutes of her just screaming, I get the gist of things: It was his mother, and she had shown up because she wanted to meet the girl her son was being cagey about. She couldn’t believe her son could do this to their family, yells a bunch of self-serving garbage, including, ‘Don’t you know I want grandkids?’ She then cries at him about his dead father being disappointed in him, calls his boyfriend terrible names, and storms out shouting over her shoulder that if he keeps up with this, don’t bother coming home.
This poor boy is just weeping silently, while his not-even-really boyfriend is trying to comfort him, completely bewildered with what happened. The boyfriend ended up calling his mom. The guy who worked with me, the teenage boys that made up my customers and I all try to calm this kid down, reassuring him that his mom was absolutely insane and he was perfectly okay the way he was.
Thankfully, the boyfriend’s mom showed up, hugged him and told him he was staying with them, and then called his mom a bee with an itch.” notasugarbabybutok
23. She Took Advantage Of The Fact That He Was Paying
“Here was the best I saw in my years of serving.
At this point, I’m working at a Red Lobster. I get sat with a young couple, maybe 16- to 17-years-old. Polite, nice, but as other servers will confirm, I immediately knew that I wasn’t going to make much, if anything, from these two. I greet them. They’re good. He’s happy. She’s happy.
I ask about a drink order. She orders a $6 non-alcoholic foo-foo drink. He gulps; orders a water. I bring the drinks, and she asks for a $10 appetizer. Ok, no problem. I can see the worry start to set in on my man’s face. I put the appetizer order in and come back for the entree order.
She orders the most expensive meal on the menu, at about $28 dollars. I look over at this kid, and I can see the math going on in his head. It’s like that part in The Hangover where Zach Galifianakis’ character is counting cards. I can see the numbers going through his head. He’s worried that he won’t have enough to cover dinner, let alone, the rest of the date.
I can totally pick up that this is their first date. She’s soaking him for every penny. I feel for him. At this point, he says that he doesn’t want anything, I tell him that I can hook him up and get him lunch menu prices.
He elects for the lunch portion of the crab linguini, which clocks in at $5. He’s beginning to sweat at this point, and I feel so bad for him.
She thankfully doesn’t order dessert. I didn’t offer because I thought he might stroke out at the table right in front of me if I did. I drop the bill; it’s like mid-fifties with tax. I get squat, nada, nothing. I knew it. It’s ok. I just hope he got to first base, really. She was taking him to town. I wish I could’ve seen where they went afterward. Poor guy. He probably dropped a whole week’s pay that night.” jwmida
Another User Comments:
“I didn’t find out until I was 23 that girls don’t usually pay for 80% of the dates they go on like I have.
It angers me that I know a few girls that actually do what you described and are proud of it, and I think it’s sadistic to expect someone you don’t know well to pay for something very special for you.” LogicalPagan
22. She Tripped, Leaving Her Unconscious And Bleeding, But Her Date Didn’t Care
“I was working in a small restaurant with two floors. A woman and a man came in, and I had a table for them upstairs.
It looked like they had a first date because they were asking those ‘getting to know each other’ questions.
After ordering food, the woman had to go to the toilet, which is downstairs.
As she walked to the stairs, the food arrived. She walked down, tripped and fell all the way down knocking her head on the ground. Two colleagues immediately rushed over to her to see how she was doing. She was unconscious and bleeding from her head, so they called an ambulance.
I went to the man while he already started eating and told him his partner (didn’t know how to call her) fell down the stairs and that she was unconscious and that an ambulance was on the way. He walked to the stairs, looked down and walked back to his table to finish his food.
Later, the ambulance arrived, and I asked him if he wanted to go with her to the hospital, and he said no while finishing her food as well. It was so awkward. He just sat there for another 45 minutes eating, drinking, paid the bill and left. I still don’t know what kind of relationship they had and whether the woman is okay.” evahoilerhoek
21. He Was Apart Of Some Strange Agency
This man is the exact person nobody wants to end up on a date with.
“In San Fran for work probably 8 to 10 years ago and at a night lounge.
In the front window sit a couple on a first date, and she is obviously scared/nervous/struggling. The guy is handsome, wearing a dark rumpled suit, white shirt, and tie (loose). Thin, but very fit. Obviously hitting drinks HARD while she’s sipping.
The guy gets up to go to the bathroom, and the girl bolts to us and in near tears, BEGGING us to get the guy away from her. He claims to be a special agent of some sort (forgot which kind – years ago), flashed a badge, threatened if she left him he’d find and could do very bad things to her and her family.
She is genuinely afraid to the point she felt she was safer in public than trying to get away from this guy alone on the streets of the city at night. We kind of panic, grab the bouncer and quickly fill him in. (The girl is back in the seat trying to look composed – remember guy just went to take a leak.)
The guy gets angrier, louder, growling about how all women are entitled and he should just get rid of them all, etc.
I had had enough, so (a bit woozy myself) I told the dude to tone it down. He LOSES it and threatens me physically.
The bouncer flashes me a look to calm down and to get the dude outside, so I do by apologizing to calm him down a bit, started flattering him, etc.
Not 5 minutes later, two blacked-out SUVs roar up, no lights on. 6 HUGE dudes in suits jump out, flash badges, DISARM (I believe, or was told this) and jam the dude in the back seat of one. That SUV immediately takes off with the guy in the back, and two very serious men begin interrogating the girl (crying hysterically by this time), the bouncer, and I about the night’s events, nicely but all business.
Evidently, the guy wasn’t lying: he was an agent of some sort. The bouncer was, in fact, listening very closely, called someone at that agency, and miraculously within an hour, they had shown up to take him away. Scared the heck out of all of us. I called the girl’s friends to come and pick her up. She obviously didn’t trust the agents or anyone else to take her home.
I’ve never seen someone so scared.
I still think of her and hope she got over that experience and moved on…” hiscapness
20. Their Date Went From Awkward To Nearly Violent Real Quick
“This happened last summer/fall 2016.
A couple comes in, approximately in their late 40s, early 50s. The gentleman (the term used loosely) proceeds to tell me they are here on an ‘Internet date,’ and he feels like he was catfished (the woman didn’t match her profile pics). Needless to say, this was going to be the most awkward table all night. Why the lady (not a term used loosely) didn’t leave immediately, I will never know.
They proceeded to order dinner, and the guy makes her order a steak, cooked the way he wanted it, and a shot of his choice of spirits. He also orders a steak and a shot.
He leaves for the restroom as I’m dropping off their drinks, and she asks me if I could please call her daughter to pick her up. I give the number to my manager to make the call.
As I bring the salads and place them down, she explains she doesn’t think the date is going well, so she has called her daughter to pick her up. He tells her she better go down on him when they leave because he’s buying her steak for dinner.
She proceeds to throw her shot in his face. He pulls out a big knife and threatens to get violent. I have to restrain him across the table while the cops are called.
Obviously several other staff (and regular patrons) come to my aid until the police come in and arrest this guy.
The woman’s daughter came to pick her up. My co-workers and I bought her and her daughter’s dinners to go.
This is why I have not tried online dating.” Heyney
19. She Stood Him Up, Forcing Him To Eat Alone
I feel like the right thing to do is stay the entire remainder of the date, even if you don’t plan on going on future dates with that person, but maybe that’s just me…
“Second-hand from a waitress serving my then-girlfriend (now fiancee) and I:
From the moment we entered the restaurant to the time we left, there was this very young and heavy kid, mid-late teens, sitting alone at a booth, eating the food on his side of the table meanwhile there was a completely different order on the opposite side, partly touched.
According to the waitress he had a date. ‘Had.’
We were all unsure as to what happened, but the guy looked… sad.
I couldn’t help but notice him, and I was genuinely unable to focus on our night, knowing that this guy was so seemingly in distress. My girlfriend agreed that even she felt bad about the possibility.
I leaned in the guy’s general direction and said, ‘Hey!’ He didn’t respond at first, but I caught his attention with the repeat.
‘Why don’t you come eat over here with us?’
His expression lit up and he responded, ‘No, that’s okay. I’m just waiting for someone.
A part of me felt rude for assuming, but we were at that restaurant for about half an hour. I don’t know who leaves a date for thirty minutes, but I felt better having asked him because at least then he knew there was someone else in that room who cared.” Reddit user
18. He Decided The Date Was Over Before It Even Started
The dude did NOT want to be there.
“I was serving one night and had a cute girl come to sit alone. She orders a drink and says she’s waiting for someone to show up, so I go back to cleaning and making drinks for the servers.
About 20 minutes later, this guy shows up and sits down next to her.
It’s a little awkward, and he immediately orders four spicy tuna rolls.
In the time it took for me to walk to the well and make a couple of drinks (after delivering his food), he’s scarfed it all down. I check on the girl, and she looks so uncomfortable, looking down and not eating.
I don’t really know what goes on, but I’ve seen couples bicker in the restaurant a lot, so I don’t think much until he barks out, ‘Hey. Need my check’ while waving a card at me.
I print out the bill and he says, ‘No. No. Just my food, not hers. Fix it,’ and I look at her again, and she’s just extremely stiff, so I pay him out, and he’s already standing up with his arm out waiting for the checkbook, which he yanked from my hand.
She calls me over when he left and said it was a first date, that he was late, and it lasted all of 15 minutes. He said, ‘I assume you ate already’ before even saying hi to her, then ordered without even asking if she wanted to eat. She said he talked with a British accent on the phone beforehand, and it was gone when he sat down.
She tried to talk to him, and he just ignored her and said. ‘Yeah this isn’t working’ then booked it.
Poor girl. We talked for a bit and I bought her drinks for her. She left me a $15 tip. She was so sweet too. His loss.” amaenamonesia
17. He Hid His Alcohol From His Date
Couldn’t he have at least waited until after the date to drink, or better yet, go on a date with someone who wouldn’t mind him drinking?
“I was the manager on duty at the bowling alley I used to work at when one of our waitresses came up to me and said there was a guy acting kind of weird.
At first, he said he wanted a drink, then he didn’t, then he did, and then said he didn’t again. She asked if I take his order when he came up again.
Right after she walked off, the guy came up to me and asked if he could order a drink. As I was ringing him up, he explained to me that he was on a blind date and he told the girl that he didn’t drink. Basically, he had been trying to sneak one in while she wasn’t looking.
After I poured him one, he asked if he could take it into the bathroom to drink it.
I said no since it’s against the rules. Then he asked if there was anywhere he could drink it where she couldn’t see, and I said, ‘Not really.’ He walks into the game room to try to drink it which was directly in her line of sight. He drinks it and then orders another.
I pour it, he chugs it, and then he asks for another. While I was pouring the third, I asked him if she would be able to smell it on him, and he said it would be fine. As I set another one down for him, I realized his date was watching and mentioned that she was watching, so he walked off.
He came back a few minutes later and is about to grab the abandoned drink when his date walks over from the snack bar and asks if the drink is his. He said no, and she asks why he’s standing in front of it. He said that I must have poured it for someone else, and I just looked at both of them.
She started screaming at him, and he still tried to pretend like the drink wasn’t his, and I walked out of sight. After she screamed at him a bit more, she got her stuff and stormed out.
The date lasted maybe fifteen minutes.
The best part was that she was his ride there, and she left him to fend for himself.” nikky_k
Another User Comments:
“It’s not a matter of her not wanting him to drink, it’s because the dude lied about drinking at all, then lied again when confronted.” Kothophed
16. He Didn’t Think She’d Mind If He Was Married
“I served at Applebees. I get way into the whole making-it-a-fun-time for those who seem like they’d be into enjoying their time there. I could tell it was the first date because of how nervous each of them seemed to be. They were probably late 20’s/early 30’s.
Also, the guy showed up before the girl and was on his phone…seemed nervous about that too.
She got up to go to the bathroom at one point as all seemed well, so I took my chance to snoop. I asked if this was their first date. He happily replied, ‘Yeah’ and told me how they’d each driven about 30 miles to meet ‘halfway.’ All is well.
20 minutes in, he stops me and asks for the check just a few minutes after getting their food. I jokingly asked, ‘Uh oh. What did you do?’ I guess that was the perfect question.
They get quiet for a second.
I realize my mistake. He says ‘Well…It would seem she is not as okay with the fact that I am married as I thought she would be….’
Still trying to keep my composure, I am curious, so I go deeper yet and ask, ‘Oh…. Well you’re at least on your way OUT of being married….right?’ Even longer pause.’ There’s a nervous laugh. I should probably just get my check now… Sorry.’
Total jerk.” mysistersthetoastgrl
15. She’d Bring Her Bratty Kids And Make Her Date Buy All Their Meals
“I worked at a family bistro outside of Melbourne, Australia, and there was a woman who used to come in with a different Indian bloke every Thursday night.
She would bring her two teenage daughters and young (~6-years-old) son to these ‘dates’ and would make the bloke pay for her and all her kids’ meals. She would even do that thing where she pretends to want to pay. Then she would order and then walk off while he paid.
The children would berate him constantly. The boy would kick him, and the girls would swear at him and throw food.
We called her ‘Tinder Kiev lady’ because she always had the same meal (even after we took it off the menu).
She would order the Chicken Kiev with every extra you could possibly fit on a plate, which ended up being about $40 to $45 bucks.
She was pure filth, and I ended up banning her from the venue because she refused to make her children behave. They would break stuff in the playground and hit other kids.
We had more complaints about this woman than any other patron and we used to have homeless people wander in and ask people for spare change!” Keegan224
14. He Was Drunk At The Start Of The Date
“I worked at a pretty nice place in a downtown area, and a girl came in to wait for her Tinder date. She was stunning: beautiful, well-educated and had a good job. About 30 minutes pass, and it was a little slow, so we had a pretty good conversation getting to know each other as restaurant employees and patrons do.
Anywho, the guy finally gets there, and they have the typical getting to know each other convo. He seemed like an ordinary nice guy. He had two drinks in the span of 45 minutes and ordered another. He seemed totally coherent, and I didn’t even second guess serving him another.
I went to the cage to grab some more stock. I was gone like four minutes, and when I get back, my fellow colleague immediately asks me how much I gave that guy. His drink was empty, no more easy-paced drinking, and he was asleep with his head on the table. This girl was super sweet and just sat there with the most confused look ever trying to gently pat him to wake him up.
I asked what happened and if he was ok. She tells me he admitted to bringing a flask and slamming it in the bathroom.
I give her a few minutes to get him to his senses, but we were starting to pick up, so I couldn’t have this dumb idiot sleeping in a crowded night spot! So, I give him a good little pat to wake him and say, ‘You can sleep, but you can’t sleep here.’ He gives me these confused lost eyes and turns to his date and starts yelling gibberish at her mixed with a few choice words. The poor girl started crying, and I jumped over the counter.
My fellow employee and I grabbed him and walked him out and told him he is never allowed in again.
I sit down with the girl to help her calm down and tell her it’s not her fault.
A few minutes later, I hear loud yelling from this guy outside just cussing at everyone who walks by. I tell her to stay inside and relax, and we will handle it. I go outside, and the guy is laying on the sidewalk yelling gibberish. I try to help him up and calm him and told him I was calling him a cab. He seemed to snap out of it for a second, and I went in to call the cab.
He left a few minutes later and got arrested because he tried to go to another watering hole down the street and threw a huge fit when they wouldn’t let him in.
The poor thing stayed for another 30 minutes with just a blank look and on the verge of tears. Before she left, she said both her exes turned out to have addictions, along with a few thank yous and a hug. Never saw her again.
It was a weird day.” 510cranemc
13. Her Ex-Husband Showed Up, And She Proceeded To Finish The Date With Him
I guess the good news is that her original date didn’t have to deal with this love triangle too deep into their potential relationship.
“A friend of mine was a waitress at a nice-ish restaurant in town.
She said a couple came in and ordered drinks, and things seemed to be going well. They then ordered appetizers and a meal.
When she came back with the appetizer, there was another guy at the table, and the woman told my friend that the gentleman would be joining them for dinner. She took his order for dinner and a drink.
She said that whenever she went by the table, the new guy and the woman were talking a lot, and the original guy was quiet. When she brought the meals, the original guy was gone, and there was some money on the table.
One of the other tables told her what happened.
Apparently this was the first date, but then the woman’s ex-husband happened to be there, and the woman invited him to pull up a chair and join them. The woman and her ex-husband then got caught up on family and jobs, etc. and didn’t respond to any of the other guy’s polite attempts at joining the conversation. Eventually, the original guy threw some money on the table and said it was the worst date he’s ever been on and left.
The exes then had a long dinner together, more drinks after, and left separately.” Ganglebot
12. Awkward Restaurant Proposal
“Paid my way through college as a waiter at a fairly well known American seafood chain restaurant with a big crustacean as the logo and in the name.
This guy and his ‘lady’ walk-in pretty late, around 8:45. Bear in mind, the restaurant closes at 10 p.m. during the week, and this was either a Wednesday or Thursday night.
Early on, the dining experience was smooth sailing and nothing special, just that he had this constant smile on his face. His somewhat greasy, long, dirty blonde hair was slicked back a bit, and he was wearing an outdated leather jacket. Think Kurt Russell, just not as good looking. He was sitting with his elbows on the table and just ordered the second round of drinks for the two of them.
She was pretty quiet. Actually quite pretty, even though she looked a bit spent for what may have been her late thirties. It’s almost like ‘overboard’ with Goldie Hawn and Kurt Russell. A bit of class, a bit outdated and somewhat trashy.
Well, they get through this giant dinner, where he’s being the perfect gentleman, whereas she’s just sitting back, nodding friendly and letting him do most of the talking. He’s a bit intoxicated at this point, and we’re already cleaning up. Maybe three other servers, the host, the manager and three or four of the kitchen staff are still there.
I’m starting to reconcile all my receipts at one of the registers, as he approaches me and hands me a ring box.
He asks me if I would please get him the hot chocolate chip cookie with two scoops of ice cream and that I put the ring in the cookie. He’s proposing to his date. The ring looks like he either got it from a pawn shop or at Walmart because the ‘rock’ was more like a grain of sand (not judging, but painting a picture here). So, I confirm that he wants me to bring this out, and he says he also wants a candle on top, plus all of the staff that’s there to ‘witness’ the event.
It’s about 10:30 p.m…in a dimly lit chain restaurant, and all these employees want to do is go home, but we’re being held up by this dude proposing to his possibly second (or third) future wife.
I gather all the employees, who are staring at me in disbelief. I think the dishwasher didn’t even bother taking off his yellow gloves, and the line cook is like, ‘Nah brah, I got cleaning to do, so I can get out of here,’ and we witness him get on one knee, and he has me walk the microwaved chocolate chip cookie with two scoops of ice cream and the teeny tiny ring over to the table, while another server is standing there with the vacuum cleaner in hand.
He proposes to her, and she says yes.
End of story. I hope they found true love.” bennelsche
11. Her Male Bestie Showed Up To “Save” Her
“I was working at a nice restaurant, and a guy and girl come in and sit.
They had just left another restaurant and were coming in for some more drinks at my place. Everything seemed cordial at first, but I think their night was starting to catch up with them. She started to get sarcastic with him and it was showing that she wasn’t feeling it anymore.
About 10 minutes later, another guy comes and joins them. The guy on the date was pretty surprised. She told him it was her neighbor, and he was basically her bestie.
After some awkward moments, the guy on the date becomes irritated and asks the neighbor guy to leave, explaining they are on a date.
‘Bestie’ guy tells him she is leaving with him and that she had called him there. Well, this angers date guy, and he makes a bunch of snarky comments that make the girl get snappy.
It ends with her throwing a full glass of water into his face while calling him names and laughing at him. She leaves with the neighbor guy, and the original guy starts complaining to me how much he spent on dinner earlier and how she wasn’t that hot anyway.
He also said that ‘women just feel so empowered ever since this women’s lib thing.’ That was one for the record books.” dusty_trendhawk
10. She Hit On The Waiter While On A Date
This woman is crazy.
“I was waiting tables one night when I approached a new table with a 65-(guessing)-year-old white man and a 20ish cute black girl.
I was thinking to myself, ‘Good for him’ and started secretly plotting my funding of young gold diggers in my 60s when the girl asked me about a scar that was on my hand. I told her I got it from helping a welder with some angles using an angle-iron, and she starts making some small talk about me being handy.
At this point, I have more tables, so I leave, but every time I come back, she keeps asking about details from my life. The guy doesn’t really seem phased by this, so I enlighten her. At the end of their date, she hands me her number in front of the guy, and I look at him.
He looks like he’s having a good time… What the heck…?
My thought was that this guy has an arrangement with this chick. Maybe she’s an escort and he could care less even if she’s flirting on his dime.
So, I take the number, smile, and walk away. Big mistake.
The guy goes totally bonkers and starts calling her every name he can muster from his lifetime of womanizing and bigotry. I’m just kind of looking from the kitchen trying not to get fired over this strange debacle.
The guy gets up, leaves, and she quickly runs after him. Somehow his orthopedic soles carry him more swiftly to his SUV, and he starts taking off while she’s yelling, ‘I’ll go **** on you!’ which is her attempt to get him to stop.
It doesn’t work though, but it gives me some good intel on how to plan my date with her.” Nukemm33
9. He Left Her With A $250 Tab
“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 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 and 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.” tjm003
8. He Showed Off His Pokemon Card Collection To Her
“Couple of years ago, I was working at a high-end steak joint.
A pretty brunette walked in and sits down. After fixing her a drink, 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. He was carrying a large bag, which he carefully set down next to him.
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 Pokemon card collection.
He set the book in front of them 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.” CaptainWisconsin
7. They Were Hooking Up In The Restaurant Until She Had An Allergic Reaction
“I’ve been a waiter for the past four years while in college, and I’ve seen my fair share of horrible first dates.
So, I worked in a dessert restaurant, gourmet desserts and cocktails, perfect date spot. And this place was just starting to come to fruition business-wise, so the current location was very ‘intimate.’ Very small restaurant that got super busy on weekends.
It was a Friday night, and a guy came in and said he was meeting someone, got him a drink in the meantime. The girl showed up, they introduced themselves and such. Things seemed to be going well, lots of laughs, and then during when they ordered, the man had slipped to the bathroom, and she ordered for him. He got a peanut butter pie, and she got a key lime pie. She mentioned she was deathly allergic to tree nuts, so I noted it and told the kitchen, etc. I took a ton of precautions to keep them separate, make sure they used separate knives to cut them, everything was going well.
When they finished the desserts, I noticed the guy using his fingers to get the remaining peanut butter mousse off the plate. I cleared everything on the table, and they seemed to be having a good time. So, it was a table that was half booth, half table. The girl moved and sat right next to her date in the booth. They both had a couple of cocktails and were both a little tipsy. Well, they started getting real touchy-feely. I told some of my coworkers ’cause, I mean, you are getting freaky in a booth in a restaurant.
So, I notice the guy start to slip his hand up her skirt…
Within minutes, she breaks out into hives and can’t breathe, making signals to grab her Epi-Pen from her purse. The whole restaurant is aware of what’s happening at this point, and I put two and two together and realize this dude just put his fingers into this chick who has an allergy.
We called an ambulance, and they ended up leaving together.” samuelaltizer
Another User Comments:
I guess she failed to mention her peanut allergy too…
“Peanuts are not tree nuts though. Separate allergy.” annagri
6. His Mom Joined The Date
Two words: helicopter parent.
“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 that looked somewhere between 17- and 19-years-old who met up with this girl around the same age. They got teas and took a seat at a table and 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 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 angry and embarrassed but says goodbye to her 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.” thirdratebread
5. Her Husband Showed Up Mid-Date
How are you going to explain that to your husband, now, Karen?
“When I was a host, I sat a couple in their mid-forties. 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 irate-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 a death glare and then marches over to the couple I had just sat and sits down opposite them.
The woman looks horrified. The irate guy is whisper-yelling at the woman, and all I could make out was that she was on a date with a man she works with, and the irate 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 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 her 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.” MajesticSamm
4. She Chowed Down On Numerous Desserts While He Sat There On His Phone
“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, and 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 notice 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 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 puts 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 breathe. I had never seen anyone devour 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 crap anymore. She walked to the counter with chocolate and cheesecake smeared on her face, looked at the cashier with crazy eyes before slapping a 50 dollar bill onto the counter.
She left in a hurry, and the guy sat there for what felt like forever with his phone down.
Weirdest shift yet.” SecretCollector
3. She Freaked Out After One Drink
“I served drinks in a movie theater. There’s a restaurant up front that not a whole lot of people come to, and I was opening up last Sunday when a woman comes in alone. I ask her if I can get her anything, and she says she’s fine. Whatever, a little annoyed that she’s taking up space on my counter, but she’s probably leaving for a movie pretty soon.
A guy walks in and sits next to her.
They talk occasionally, neither having ordered or anything. I ask if they’re seeing a movie, and they say, ‘No, we missed it. We’re trying to figure out something to see.’
The guy decides to grab a shot, and the girl gets a Tito’s and diet coke.
Without warning, she goes off and yells for the whole area to hear, ‘I’m just too fat.
I can’t have a freaking vodka with a regular coke! Am I too fat? I just want answers!’ She calms down directly after, though, so I don’t think too much of it, and I decide not to do anything.
These outbursts repeat. They occurred in several contexts. ‘Am I going to prison? I just want answers!’ It was kinda funny, but really sad, especially when she got a call from what I assumed was her dad about halfway through and starts yelling obscenities at him. I’m about to get a manager up here to ask her to leave (policy) when she leaves toward the restrooms.
She comes back and sits on the other side of the bartop and the guy and I look at each other. We get talking, and they’re on a blind date. Drove about 60 miles from Oklahoma to come to the theater.
He grabs one last shot and downs it before asking her if she’s ready to leave, to which she responds, ‘Does it look like I’m ready? I’m not even done with my flipping drink!’
They ended up leaving. She stormed off without paying for her drink. He paid for his. I learned later from the girl working the ticket counter that she left the bar, so she could go cry very loudly in our souvenir photo booth.
I hope he made it home okay.” CinoSRelliK
2. He Dragged Her Out Of The Restaurant
“Many years ago, I was a 16-year-old hostess at Bennigans (American-Irish pub food).
Two couples came in for what looks to be a double date. It’s a quiet night, and they’re seated near me, so I people watch a bit while taking care of other things. The guys sat across from each other on the inside, and the ladies are on the outer edge in the bartop booths. The bartop booths at our location were elevated around 8 inches, so there was a step up into the booth making it quite high.
The men loudly drank and toked and talked while the ladies talked fairly quietly, and one seemed to work hard to pry the other into talking a bit.
After the appetizers and just before their entree, the quiet lady comes out of her shell a bit. She says something and nudges her date in the ribs a bit while chuckling. Everyone is smiling for a brief moment before her date turns red in the face, stands up, backhands her out of the booth, and starts dragging her out of the restaurant by her hair while screaming curses at her.
She’s crying and begging for him to let go, apologizing the whole way.
A lot of us were frozen in place then everyone suddenly starts moving. Servers were running out of the restaurant, and I’m on the phone with the police.
He throws his date into his SUV, and the other couple gets in the same car quickly. Dude hauls butt, nearly running over a server as he backs out. We gave the vehicle description and plates to the police – it was obviously a dine and dash on top of him beating up on his wife/girlfriend. I never heard if anything came of it.
This was nearly 15 years ago, and I still think about her. I wonder if she’s ok and ever got away from him. I hope she did.” painahimah
1. He Wouldn’t Stop Bragging
I bet he won’t be bragging anymore when he realizes the only women who will show interest in him in the future will be those after his money.
“I lived in a small town at the time, one of those ‘gotta escape from here’ type places. I was at a brewhouse with a friend enjoying the evening off work and witnessed an absolute trainwreck. A guy who moved away comes back to meet up with an old fling, and he’s just trying so hard.
Bragged about his healthy six-figure income, bragged about how worldly he’s become. He talked about himself like he was Elon Musk for the entire date without allowing a single shift in the conversation to allow for anything but himself. Poor girl just sat and politely responded with one-word answers of encouragement when she was allowed to while this torrent of exaggerated success gushed out towards her.
I’ve never felt so bad for someone in a date situation before. She started the date so impressed and seemed very into him, but was just so clearly over it by the end.
The guy likely did have so much going for him (exaggerated but even without embellishment) but just refused to ever stop talking about himself. Hilarious but brutal.” heyman-
Third-wheel helicopter parents, arrogant dates who think they’re all that, dates turning out to be already married… Boy, these first dates must have been incredibly awkward, and those aren’t even the worst dates that I’ve compiled! I think there’s some advice we can take from these messed-up dates: always perform background checks, split the bill, and leave your Pokemon collection at home.
Oh, and do us all (and your bowels) a favor: don’t ever try to impress your date by