There's never a dull moment in the restaurant business - especially when servers are tending to couples on dates... And these date stories were anything but cute... (Content has been edited for clarity)
"Many years ago, I was a 16-year-old hostess at Bennigans.
Two couples came in for a 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, the ladies on the outer edge of the bar booths. The bar 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 smoked and talked while the ladies talked fairly quietly, one seems to work hard to pry the other into talking a bit. After the appetizers and just before their entree, the quiet lady came out of her shell a bit. She said something and nudged her date in the ribs a bit chuckling. Everyone was smiling for a brief moment before her date turned red in the face, stood up, backhanded her out of the booth, and started dragging her out of the restaurant by her hair while screaming curses at her. She was crying and begging for him to let go, apologizing for the whole way.
A lot of us were frozen in place, then everyone was 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 out, 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."
"I approached one of my tables and a guy was sitting by himself, waiting for his Plenty of Fish date. He downed a couple pints before she got there, but since he was kind of awkward, I assumed it was liquid courage. She got there, and when I asked her if she wanted a drink, I could tell she wasn't going to have one, but saw his half-empty drink and thought she had to. She ordered a drink special and seemed super weirded out at the fact they were drinking on the date.
The guy continued to order pint after pint. He hadn't touched any of his dinner and was doing one of those 'let me tell you about the government', half-eyed, slurred speech, too loud type of conversation with basically himself. She was NOT impressed.
A little while later, the girl was gone and left a full drink and empty plate, and the guy was sitting at the bar top. I asked him to settle his tab with me and he complied. He then went into spilling the beans on the whole date. He goes: 'Y'know, I tried this online dating nonsense and it's just trash. She said she was athletic-built, but she wasn't. She was HEAVY SET. There's a box to check for that.' Then, he looked up at me, bad breath and all, and looked me up and down really slowly, and said: 'Now YOU... you're athletic built. What time are you off? Is the bartender your boyfriend? I swear I can fight him...' to which he leaned too far and almost fell off his bar stool. He got removed from the bar shortly afterward for being too wasted and pestering other women, telling them what Plenty Of Fish box they should check off."
"I had a couple come to dine in, and they had the three-course meal and everything. The guy had mentioned to our host that he was proposing, so we arranged a bottle of bubbly to be delivered to the table once dessert was ordered (that's when he was planning on proposing).
Dessert is ordered, long awkward silence at the table. She's tearing up, grabs her purse, apologizes and leaves. Thankfully, we had all been keeping an eye on them (we wanted to see a cute 'yes!' moment), and the server didn't put through the order for the drink. We all could see it was a rejection.
Ten minutes later, his parents arrive, and tell the host that they're excited to 'meet their future daughter-in-law!'.
I'll never forget that poor host's face as she led them over to his table. Him alone."
"Boyfriend and girlfriend came in with their five kids. They've been together for over 10 years and she told us she wanted to propose to him. She told us to bring out a dessert with a candle in it and then she was gonna pop the question. So that time eventually came, and 8 of us went to the table with the dessert.
She starts giving this speech about how they've been through so much, made five kids, blah blah. 'Will you marry me?'
The guy looked at her, 'No.'
Horrible! I felt my jaw clench and my cheeks get hot from second-hand embarrassment. Slowly we all started to back away and disperse from the table. The woman was silently crying while the guy kept picking at his food. The kids literally looked like they couldn't give a care they tried. They were laughing and eating and talking amongst themselves."
"I had a middle-aged gentleman come into the restaurant. This place is fine dining, white chairs and tablecloths and silver service. He was trying, but was noticeably out of place and uncomfortable. He was extremely awkward, kind of chubby and not at all attractive and spoke with a lisp. But he was super sweet and friendly. His date walked in and I knew right away this was an internet or blind date. She sat at the table and just about immediately turned her nose up at him. She ordered a very expensive drink, and I saw him do the mental panic thing a lot of our less financially well off customers do when they see the prices on our menu. I served the bottle, feeling pretty bad for the guy at this point because man, he was giving this date his all and she was seriously acting like he wasn't there. Then before the apps came out she went to use the restroom and never came back. He sat there alone for over an hour and finally asked for the check. He handed me three different cards and asked to split it between them and let me know if either of them declined. I talked with my manager and explained what I witnessed and she agreed to discount everything down to cost (so he ended up paying only about 30% of the bill). The poor guy started bawling when I brought the check back to him and spilled the entire story.
Apparently, this lady was a friend of a friend he had been attracted to for a long time and when their mutual friend set up the date, he really wanted to impress her by taking her to the nicest place in town but didn't realize how expensive we were. Then the woman saddled him with the cost of one of our most expensive bottles and ran out. I felt so bad for the poor guy. I mean, I understand that the date obviously wasn't what she expected. But that was a terrible thing she did.
Because of the nature of that restaurant, I've got tons of great hilarious awkward date stories (prom season was always full of great times!), but this one actually ticked me off quite a bit."
"A guy made a reservation saying he was going to propose.
He asked for a special table and for dessert to come with a sparkler candle and, 'Will you marry me?' written on it. I bring out the cake, the manager follows me with two glasses of bubbly, my co-workers are cheering.
We set everything down and walk away. They end up having a serious, quiet discussion and it is very obvious that she is rejecting the proposal.
Then three of their friends show up and sit at the table, all excited thinking their friends just got engaged. But it quickly became apparent to them that it was not the case. It's very quiet and awkward at the table. The woman who was being proposed to left and the rejected man and his friends got wasted. He gave me a 20% tip too, which was nice considering how horrible his night had been."
"I was not a server but a kitchen manager and head cook who was called to a table one night. It was one of those 'we want to meet the chef' things. I put on a new chef coat and go out to the farthest reaches of the dining room to where earlier in the night we all noticed that the people there had asked to have the lights turned down.
As I'm going there, one of my server friends says quietly 'buckle up for that.; I get to the table and greet a very well dressed college kid, probably no older than 20, who is not drinking or eating and is sweating profusely while sitting straight up in his seat like a mannequin. Then I look at his date. She was probably in her 50's or 60's, painfully thin, tan sagging skin, too much neon pink lipstick circling busted up yellow-gray teeth, she's got an empty bottle in front of her and a ton of hoop bracelets. She's grinning at the guy and in a split second, I could tell she was using her feet to rub the guy's crotch under the table. I exchanged some pleasantries with them for a minute and the guy asks if he can see the kitchen real quick because he used to work at the same restaurant but in a different city. I say sure, we'll be right back, etc.
As soon as we're out of earshot, he says that his friends had set him up on a blind date and that woman is obviously a streetwalker. He was freaking terrified...like hostage situation terrified, so I told him I'll let him out the back door through the kitchen. I haven't seen anyone power walk to their car like that in my life. And with that, he fled. Funny thing was that the lady he was with paid for both of their meals and left a large tip."
"I'm a bartender. Witnessed a Tinder date at the bar top. Convo started somewhere with, 'I have 7 panther tattoos. I just feel I really identify with the Panther.'
Somewhere after that, he spotted my tattoo of some molecular structures and asked what they were. I explained and he said, 'I'm more of an anatomy man myself. WINK'
Heard a snippet of, 'All my past infidelities were never my fault. All the girls seduced me. I'm a man that just can't say no.'
Then ended when he asked the woman what she would do if she broke her leg while mowing the lawn. The poor lady just looked at me and said, 'We're ready for the check,' with the most defeated look on her face."
"I waited tables in a small town when I was in college. We were one of the only restaurants in town. I had an early 20's couple come in one Saturday night and it was obvious that they were on a first date. The guy was trying to impress the girl by being a real prick to me by ordering me around and belittling me. I can handle that, just kill 'em with kindness.
So every time he was condescending or rude to me I just gave a nice 'yes sir' or 'right away sir' and did my job. He was so bad that other servers noticed. When he barked at me for his check, I promptly provided it for him. As he took his wallet out of his pocket, he dropped a rubber on the ground. I picked it up and put it in on the table between both of them and said, 'Sir, you dropped this.' He denied that it was his and I said, 'Yes it is, I just saw it fall out of your pocket.' His date was furious.
She immediately asked, 'What's that for? What did you think was going to happen tonight. We just met!' He tried to play it off but she got up and exclaimed, 'Pay the bill and take me home, now!' She then turned to me and said, 'I'm sorry' and walked away.
I gave him his change right there and he said, 'Thanks, Bro.'
I told him, 'Anytime!' I didn't get a tip, but another table next to them saw the whole thing and became some of my regulars.
This happened in the mid-'90's (I know, I'm old) in a pretty conservative part of the country. The girl didn't look like the type that was down to sleep with the guy on a first date. "
"I worked at a breakfast diner. A couple came in. I remember almost exactly what they ordered: she had oatmeal and a fresh fruit cup, and he had banana french toast, three eggs, sausage, bacon, hashbrowns, and toast. She got a mimosa, too, and he just had coffee. Every time I went to check on them, he ordered something else. More bacon, more hash browns, etc.
The average bill for two people at this restaurant was between $15 and $20. This dude racked up a $40 bill. The time came to drop it off, and I went back and he said he forgot his wallet, so she put her card down. I went to the card machine and it got declined. I returned to the table and told her it had been declined. She called her bank and I assume they said, 'Tough luck,' so then she said she would call her mom for money to be deposited.
The call got heated so she stepped outside. I could see her pacing and cry out front. She came back in tears and said something to the dude. Then she left.
I went over and said that he could run home and get his wallet. He looked at me and sighed irritably as if I had inconvenienced him. Then he reached into his back pocket, threw down some cash, and left.
It was a really small town, so this was the topic of discussion for a while with our regular customers."
"I had a regular sitting at my bar in a chain restaurant about two weeks ago. He sat there for an hour, left for 20 minutes or so, then came back complaining that he'd been stood up. The date was supposed to have arrived an hour before he mentioned anything. Poor guy.
All of a sudden, this woman appears, apparently his date. Nothing out of the ordinary about her except for the fact that she was an hour late, so I continued making drinks for the restaurant.
A couple of minutes later, a waitress comes up asking if the woman was on a date with the guy at the bar. I respond yes and ask how she knew. She told me that the woman had just left her (the waitresses') section and had been on a date with another man."
"I used to work in a place that did Saturday brunch, and I happened to be working a brunch-dinner double that particular Saturday. My very first table of the morning is a guy who gets there and sits at a table for two, says the other person is coming. He'll just have a water while he waits. Cool, low maintenance for a little bit.
Like half an hour goes by and no one shows up, and he still refuses to order anything. Finally, FINALLY this girl shows up and it's obvious it's the first date and they don't know each other well. She orders a mimosa, he sticks with water, they seem happy to see each other. She looks very cute for a brunch date, fun patterned dress and light makeup.
They end up sitting at my table for the entire shift pretty much. Every time I walk by, the guy is talking about himself and the girl is nodding politely. I also happened to pick up from multiple passes by the table that he went to an Ivy League school, so I can only imagine how many times he managed to bring it up that I didn't hear. He's smiling and laughing, she is too, so it's going...okay, but he still talks too much. He's also ordering really cheap stuff, and I even caught him eating off her plate at one point. They finally leave and he pays, but my tip is really terrible, which I was kind of surprised by because he seemed like a well-spoken young professional. Whatever, I go home to take my break and let my dogs out.
Come back for the Saturday chaos, and a few hours into it, I spy a familiar patterned dress across the dining room. It's the same girl, wearing the same outfit but heavier makeup, sitting with another guy. I go flag down the server who has their table and she says it's obviously a first date. I relay the events of that morning and she thinks it's hilarious, so she transfers the table to me just to see what happens. I go over and run their drinks, and she doesn't pay attention to me, but they seem to be chatting and smiling and having a way more animated conversation. Drinks are flowing, they order apps and entrees and the whole nine yards. This guy just also seems to be a lot more charming.
Finally, I decide to stop being an invisible server and mess with her a little, so when she walks by me to the bathroom I tell her I love her dress and meant to ask where she got it earlier. She knows that I know, but she takes it in stride and laughs. Later in the night, they've run up a big tab, dude pays, leaves a big tip, I see them hugging outside.
Good for her for hustling two free meals in one day, though.
I also worked on a really disastrous sugar daddy-sugar baby date, but that's another story."
"It was a pretty busy Friday night at a bar I used to work for. This guy (who comes in regularly) came in with two girls, both very visibly expensively dressed. Obviously, he was in a very good mood already, very jolly, and ordered the most expensive bottle we carried for the girls, and a few drinks for himself, and then another round. They sat together at the bar, with the regular in the middle.
After a while, he started, out of nowhere, 'bragging' about his intimate-life. I nearly lost it and had to get down behind the bar. The ladies smiled politely and excused themselves to the bathroom, one after the other. When they came back, they sat facing the opposite side next to each other - away from the bar, opened to space. The communication between them and him was stagnating as he became more and more wasted. Then he dares them to kiss each other, and they did it absolutely passionately. This brought them much more looks from other gents in the mood for some in the pub, and of course, it led to more than just looks.
He went home, alone, like two hours before them. He paid for the expensive bottle but did not give me a tip. The ladies had a great time. As I closed, they were headed to another bar. Sometimes I miss this stuff."
"My wife was a server at an upscale restaurant and I'll never forget this story she told me.
It's Valentine's Day, so the place is booked for the entire night and this guy shows up, looking to get a table without a reservation. The hostess tells him that they are booked solid and unless there was a cancellation, he wouldn't be able to get a table soon. The guy seems to accept this ok and goes to the bar to have a drink and wait for his date. Girl shows up and this guy is on his third drink and getting loud. She meets him at the bar and looks disappointed about the table.
As they are discussing what to do next, things go sideways as the guy screams about 'how that dumb hostess lost his reservation that he made a week ago and he isn't leaving until they've got a table, blah blah blah.' The poor hostess is a basket case and trying not to break down as the guy's date goes as pale as a ghost. The manager obviously comes out to see what the problem is and the guy repeats his loud tirade against the 17-year-old hostess. Luckily, the manager has a spine and tells the man to immediately leave before he calls the police. He refuses, so the manager calls the cops and the guy decides he has made his point and tries to run, neglecting to pay for his drinks.
The manager runs out gets his plate number and almost gets hit by the wasted idiot as he is trying to flee. H still gets pulled over by the cops, fails a sobriety test, and the manager presses charges for assault and theft. This guy's poor date is now comforting the hostess, who by all accounts did her job and got lambasted for it."