Not all dates are destined to go great, but these dates are the stuff of legend...bad ones, that is. These horrendously bad dates were seen by servers and now those servers are spilling all the juicy details of what went wrong.
He Walked Out On Her Special Day
“I used to work at Olive Garden and one day a coworker of mine waited on a man and a woman who were apparently fighting. After their entree, the guy gets visibly angry, gets up, and leaves. The woman was sitting there crying when my coworker approaches her and asks if everything is ok. She asks if we come out and sing for people’s birthdays, and he tells her that we do. She then proceeds to order something off of the dessert menu and asks that we come out and sing for her because it was her birthday. She was still crying when we came out to sing, it was probably the saddest thing I saw the entire time I worked there.”
They Were Already In A Foul Mood When They Came In, And Things Did Not Get Better
“I waited tables for a short time about five years ago, during that time I only remember seeing one date go absolutely terrible.
They were both obviously upset before they arrived, very polite to me, but didn’t say anything to each other when I came to the table. It escalated, the whole restaurant could hear them fighting, then finally she said something like, ‘Fine, go have fun with your other woman!’ and she got up and stormed off.
He stayed, paid for the food she already ordered and had it put in a to-go box, and had three or four beers. The whole time he just stared out the window, playing with his wedding ring, which he had taken off.”
The Date Ended Up In Him Getting Arrested
“I work in a country bar and a man brought a girl in for her birthday. She was having a great time, having jello shots and what not. Next thing we know she’s out in the parking lot passed out. Turns out he put muscle relaxers in her jello shots not knowing she had severe asthma. I’m in a small town so here everyone knows everybody. These people we didn’t know and were just fine and seemed normal. When everyone realized what happened, the guy tried to take off. 10 or so regulars (big dudes with cowboy hats who don’t take this stuff lightly) surrounded his car and made sure he didn’t leave until the cops showed up.”
The Worst Part Was That This Wasn’t The First Time This Had Happened
“Once had a guy come in on Valentine’s Day with his date. I asked how long they were together. She said two years and that it was their anniversary. She seemed very excited, but the guy was very blah. They were eating their dinners when I came by to check on them. The guy was complaining about everything, but I gave him excellent service the whole time. The girl seemed very uncomfortable most of the time. She was very polite to me, however, but she was very touchy-feely to the guy, she was rubbing his neck and kissing his cheek, but he seemed uninterested. Sometime in between dinner and dessert, the guy got up and went to the ‘bathroom.’ The girl sat there for two hours. She was crying hysterically for the last half an hour. After repeatedly trying to calm her down, I paid for some of her tab and sat down and listened to her vent before offering to get her a cab. She kept saying that she hated when he did stuff like this (implying he had done it before). I told her she should probably move on. She looked offended and said, ‘No, you don’t know what you’re talking about, he’ll come back for me. He’s just mad because he doesn’t like spending money.’ She got up and went outside to wait on a bench in front of a restaurant. She waited there for an additional two hours. He never came.
That was so cold.”
He Took Advantage Of Such A Sweet, Vulnerable Woman
“This is so awful and honestly just the worst. A man and a woman came into the restaurant, and they seemed very nice and friendly towards each other. The woman had Down’s Syndrome, and the man, who was doting on her in an obviously romantic way, did not have Down’s Syndrome.
They sit down and start eating. They seem to be having a really great time and were enjoying their meal. The restaurant started to get really busy, so I had less time to spend monitoring their table, but I kept my eye on them. I noticed the guy wasn’t at his seat at one point, but I figured he was just in the bathroom. When I looked back a bit later, he still wasn’t at his seat. I thought this was strange, so I went over and asked the woman how everything was going and to try and gauge where her date went. She was still happy and explained that he had to run and make a phone call.
I looked back again later, and she was still waiting, but it became increasingly obvious that he had dined and ditched her. I went over to chat with her a bit, and she seemed anxious because he still hadn’t returned. I started asking her a bit more about him, and it turns out that she had met him that day at the coffee shop where she worked.
Having to explain to her that he probably wasn’t coming back was one of the most heartbreaking things I’ve had to do. He had disappeared for an hour at this point.
Eventually, she explained that she didn’t have enough money to cover the bill, but we, of course, told her that she didn’t have to pay. She also didn’t know how to get home, as he was supposed to give her a ride. She had her guardian’s phone number, so we called her to come pick her up. The guardian was very upset and tried her best to console the guest. Her guardian ended up insisting on paying us for some of the bill and taking her home.”
He Was So Excited To See His Internet Date…
“We had a guest call in advance to make a reservation for a table for two. He asked to place a tablecloth on our best table and have our best white wine waiting and that he would be having flowers delivered as well. The day comes and the place is pretty empty and I’m the only server working. I have the whole table ready, everything is perfect. The man comes in. He’s wearing a suit, bow tie, the whole shebang. I show him to his table, he is just as sweet as can be and tells me he’s waiting for his date. They met on the Internet and this is the first time they’re going to meet. He waited there for four hours. The woman never showed up and my heart broke into a million pieces.”
Something Tells Us They’re Not Going On A Second Date
“Overheard a first date in a restaurant. They introduced themselves to each other, started talking.
Later, the girl mentioned how she liked to sew her legs together. Dude said, ‘I’m…not really sure what you mean.’
‘Oh yeah, it’s a total dominance thing. Like, I sew my legs together and then get told to walk around and stuff.’
Guy again, ‘Uh, why? I don’t really…get it.’
‘Well, it’s all about the dominance. It’s hot because you have to struggle to walk around in pain and do what the other person wants.’
Guy said, ‘Well, that’s not really something I’m interested in…’
He handled it really politely but clearly was freaking out. I’m so glad I’ve never been hit with that.”
His Date Barely Had The Chance To Finish Her Appetizer Before He Broke The Bad News
“I used to wait tables at a place in Denver and a lot of people would dine at our restaurant prior to going to the opera/theatre.
A couple came in and sat down, started eating appetizers and drinking drinks, and were obviously dressed for the opera. After about 15 minutes, the guy got up and walked away — and his date was crying.
The scumbag didn’t go far, however. He moved to the next floor down (of the same restaurant) where his NEW girlfriend was waiting, sat down to a fresh cocktail, ordered dinner, and took the other girl to the opera.
It was douchebaggery of the highest caliber.”
The Worst Part Of The Proposal Isn’t That She Said No
“A couple of years ago I worked at PF Chang’s. It was Valentine’s Day. The guy came in hours earlier to request we keep his huge bouquet in our refrigerator until he came in with his girlfriend for their date. We did. When the couple arrived, we brought it out, the server took their order, brought out a bottle of the most expensive wine, and they had just gotten their lettuce wraps when he proposed. Every server and host knew what was going on, so we were all excited. APPARENTLY, the girl said NO, and instead of just leaving, they both stayed there and finished their meal. They sat there opposite each other (were originally cuddling in the middle of the booth) with the giant bouquet blocking their view of the other for half an hour. They could have taken the food home, but NO! It was so awkward and sad.”
The Date Was Bad To Begin With, But Then Someone Took A Tumble
“A guy who has frequented my bar enough that I’d say he was closer to a friend than a regular came in looking a little more done up. He told us he was finally meeting a ‘young lady’ who he’d found through, I kid you not, ancestry.com.
Mind you, this guy is a veteran in his 70’s. He’d told us before that ancestry.com is like a dating website for people his age. They apparently had gone to the same elementary and jr. high, but 10 years apart. He’d been chatting with her for a few months, but they’d never met because of the distance.
Now, this bar is anything but fancy, it’s your typical old school college bar, very small, but comfy and because it happens to be located in one of the oldest buildings, you have to take a back (slightly sketch) alleyway to get there. The food is great, but it’s bar food and the atmosphere is what you would expect from a college bar so you can imagine this lady’s surprise when she walked in wearing a little less than a gown expecting a drink in one of the oldest buildings and with a distinguished pilot and war vet.
This date was just destined for disaster. First, this lady had gotten lost. He had apparently told her it was a side street, not an alley. Second, she had shown up around 6:30 when we’re usually pretty busy just with the dinner crowd. The third reason this was going to fail: while he could have prevented the first two, he could not have known we were going to get pretty much the entire Greek life’s pub crawl stumbling through the bar at the exact time she was. This lady had to navigate puke in high heels through an alleyway. Upon arriving, she was greeted by an old man with a moustache longer than the straw in his drink. You could see this lady had had enough before she ever walked in, but I think the moment that absolutely took the cake was after she had gotten over the initial shock. She had already sat down and he was slowly winner her over. She ordered our ‘speciality’ mac & cheese bites, essentially fried macaroni and cheese balls, as an app with her non-alcoholic drink. He began telling stories and the conversation was going great, but our war vet who normally could pound quite a few back was clearly getting pretty drunk. He’d finished maybe four beers before she came, and was slowly drinking his fifth when he started leaning back — and then he just flopped. He caught himself, but he was clearly drunk. He’d taken a pain pill to calm his nerves and the resulting intoxication had left him wobbly. My manager ended up driving him home, but this little old lady, who I’m assuming had nothing else to do, ordered a Long Island and mercilessly hit on every single drunken frat guy before finally making out with a freshman and making her way home.”
Reminder: Hooters Is Not A Great First Date, Especially If There’s Self-Esteem Issues Involved
“I saw some pretty awful dates while working at Hooters. I’m still not sure what possessed one guy to bring the girl he had only had one date with to Hooters for Valentine’s Day. She didn’t eat much and I don’t think they spoke more than half a dozen words during their entire visit.
Even worse was the couple I served who ended up in a screaming match in the parking lot. She was obviously uncomfortable from the moment that she walked in and her boyfriend knew it. He repeatedly asked her if she wanted to leave before they had been shown to their table. She kept shaking her head, though, even as her eyes were shooting daggers at every waitress who passed by.
I was as friendly as possible while also making myself scarce, figuring that whatever insecurities were driving her behavior would only be made worse by the continual presence of a girl in hot pants and a push-up bra. She refused to speak to me after I took the drink order, and by the time I had their food order, she was teary eyed.
Shortly before I expected the food to be finished, I stopped by their table to let them know. She ran towards the bathroom before I got there, and her red-faced boyfriend sheepishly asked if they could get that order to-go. I told the cooks, who were just dishing up the food, and they transferred it to to-go containers, but when I turned back to where the couple had been sitting, I realized that neither of them were there.
A rush of new customers at the bar prevented me from checking the bathrooms for my missing table, but the newcomers quickly filled me in. Apparently, as they entered the restaurant, the girl ran past them, followed by her boyfriend. When the two reached the parking lot just outside the entrance she began sobbing and shouting, angrily asking why he had brought her there. A quick peek outside confirmed this tale. She was stamping her feet, gesticulating wildly, and he appeared to be making a few half-hearted attempts to defend himself.
A bit later the guy returned for the food that they had ordered. He looked awfully glum, and when I asked if everything was going to be okay, he just shrugged.”
He Was Treating Her So Badly, She Ended Up Getting A Ride Home From Some Friendly Cops
“So it was a UFC night, there was the tool-bag meat-head guy and this beautiful woman sitting at a table in my section. All night long I got to hear him either cheer on his guy or belittle his girl. She was almost in tears the whole time. Just as he was getting up the use the bathroom, I overheard him say, ‘Stay here, dummy.’ Once he walked away she burst into tears. I came over and sat in his seat and asked her what she wanted me to do.
‘I just need to go home, he’s a friend of a friend and this is our first date.’ She shrugged her shoulders.
‘I’m guessing you just need a ride.’ She nodded. I thumb over to the four cops that usually hang out during fight nights: ‘One of them will give you a ride.’ She threw a few bills on the table and I asked the cop if he’d take her home. He saw her tear-streaked face and said that he would. I informed the cops that the guy might be ticked and start something. The guy was ticked alright, but nobody in the area told him that I was involved, he paid (no tip) and left before the fights were over.”
The Date Went Well, Until Someone Recognized Him
“I had a woman at one of my tables. A couple was seated at a table across the room and they were being lovey-dovey, snuggling on one side of the booth, kissing, etc. When the woman at my table saw the couple, she completely freaked. It was her sister’s husband with some other girl. She was fuming to me about how she has always known he was a cheater. She gave me her card and paid for her meal (which she had barely touched) and then marched over to his table with her phone out, yelled his name along with some choice phrases, all while snapping pics of him and his paramour.”
“She Waited Until I Was At The Table To Make Her Big Announcement”
“Being a busboy, all I really had to do was clear tables and make sure drinks were filled. There was one table who had been arguing nearly the entire time they had been seated. When they had finally stopped and were sitting in silence, I decided it would be a good time to refill their drinks. As I was filling up the man’s water, the woman snapped, ‘I want a divorce,’ and then promptly got up and left. Awkward silence ensued, but the guy didn’t seem too upset. He ate his steak as well as his wife’s and tipped thirty percent.”
He Went To A Diner Expecting 5-Star Service
“I waited tables for a few years at Baker’s Square which is maybe a step up from Denny’s. Maybe.
One night, a man and woman appear at one of my tables. He was wearing a tuxedo, she was wearing a killer red evening gown. He had apparently decided to paint the town red and show her the night of her life — by coming to Baker’s freakin’ Square. I suppressed some laughter and approached the table respectfully.
She was quite polite, timid a bit even. He, however, thought he was dropping two grand at the Four Seasons. He snapped his fingers for my attention more than a few times, kept calling me, ‘waiter,’ in a really snotty voice and no, he wasn’t joking. He was taking this very seriously. And she kept giggling at him. It was obvious she thought he was being ridiculous and most likely would have a story to tell her friends when this date was at its merciful end.
I was getting a little annoyed at his attitude but I managed to keep a lid on it. Then he asked for the ‘Wine List.’
We don’t have a wine list. We sell two bottles of wine, one red, one white, same brand and both in a 1-glass size plastic bottle. I politely explain the situation to which he sighed in annoyance and waved me away, saying, ‘Well, get me some then — Red.’
So, I brought him a mini bottle of red wine and I twisted off the cap.
‘Would sir like to sniff the twist-off cap?’ I asked in a British accent.
He turned red with anger. She started laughing so hard she nearly fell off the chair, which only makes him redder. He grumbled something akin to, ‘No, thanks,’ and the evening progresses with far less snobbery.
He did leave me a nice tip, which I’m assuming was all part of the bizarre attempt to impress a girl with a fancy meal at cafe choke and puke; An evening I’ll never forget.”
The Date Was Going So Well…Until His Family Showed Up
“I worked for two years at a fairly popular chain restaurant. One early evening, a couple walked in and were sat at the table closest to the door. They ordered mussels as an appetizer, which consisted of about 30 mussels in a giant bowl filled with quite a bit of lemon butter sauce. Shortly after we delivered the mussels, a woman pulled up to the front door, unloaded three kids from the minivan, and stormed into the restaurant. She walked straight past the host stand, where myself and several other servers were chatting, walked straight up to the table with the couple, pointed at the woman and said, ‘Kids, this is the woman your father is cheating on me with.’ She then picked up the mussels and poured them in the woman’s lap. The man at the table stood, grabbed her by the arm, led her and the kids back out to the car. He came back in, helped the woman clean up, and they finished their meal.”
Drink Throwing Is A Sure Sign A Date Isn’t Going As Planned
“I’m not sure if they were getting married or just dating, but I was waiting on a table who were having a pretty intense whisper fight when I walked over. I got their drink orders then walked away. When I came back, they were sitting in stony silence.
Well, I did my job, got their orders and then went to work on other tables. The next thing I know, the woman was standing up, practically yelling at the guy, and I have to paraphrase because I can’t remember exactly what was said, but it was along the lines, ‘You’re the most worthless piece of crap, and your mom is even worse; It’s off.’
She dumped her drink on him, then strode over to me. I thought I was about to get yelled at too, but she yanked open her purse and fished out a five and said sorry for the mess.”
He Thought He Was Pretty Smooth With That Last Move
“I once worked at an Italian restaurant that was popular in the area for local business people on their lunch breaks.
One day a man, eating alone, saw a woman he liked, also eating alone. He asked me to ask her if it’d be all right if he joined her. She said yes.
All seemed to be going well, because when I brought them their checks (separate, of course, don’t want to make any assumptions) he had her card with her phone number in front of him.
He watched her pay her bill, she tipped generously and he handed me just enough cash to cover his bill, saying to her, ‘Looks like you covered the tip.’ He smiled at her while he said this, like he was being clever. She reached across the table, grabbed her card and excused herself while he just sat there dumbfounded.”
She Handled That Break Up Like A Total Boss
“Right before I quit waitressing at a restaurant a few years ago, I had a lesbian couple come in. Over appetizers, I overheard one admit to cheating. After 10 minutes of arguing, the woman who hadn’t cheated made me bring the check, which the cheater paid. After signing the receipt, the woman who was cheated on forced her now ex-girlfriend to leave so she could eat her free meal in peace.”
He Legit Started Crying Over Milk
“When I was 16, I was a waitress at Applebee’s.
Apparently, Saturday was night date. Cute guy and cute girl, both in their early twenties, came in. He ordered milk, but I wasn’t entirely sure we served milk. I asked everyone and no milk turned up, so I went back to tell him and he was clearly upset. Obviously uncomfortable, the girl tried to diffuse the confrontation over some stupid milk, but to no avail. The bartender finally turned up with some. Everything went okay from there until he spilt his milk. Grown man, spilt milk — he literally started crying and left to wait in the car. She asked for the food to go.”