If a first awkward date is weird for its participants, then it's bound to be a painful night for the poor man or woman serving them. These servers relive the moments they were glad not to be either of these two people on their dates but felt sorry they had to serve them.
After This Date She Literally Bolted Out The Door
“Couple comes in on Valentines Day – no reservation. They get seated at the bar, order some drinks and apps, and are sitting there chatting and laughing. Seems pretty normal.
After finishing their apps, the guy drops to one knee and pulls out a ring. Girl immediately shuts him down. He didn’t so much as get a word out before she’s saying, ‘Nope. Nope. Nope.’ Grabs her coat off the back of her chair, and is putting it on, still saying ‘Nope’ over and over. Practically RUNS out of the place, does not look back.
He looks gutted. Pays the bill, walks out, staring at the floor the whole time.”
Even To This Day, This Server Never Forgot About This Poor Woman
“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 seeming to work hard to pry the other into talking a bit. After the appetizers and just before their entrees, quiet lady comes out of her shell a bit. She says something and nudges her date in the ribs a bit 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’s 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 tail, 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.”
This Server Already Knew This Lady’s Antics After Her First Order
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“I work at a nice but not fancy restaurant. A lot of people dress California casual. A young couple comes in one night, and the gentleman is dressed in slacks and a button-down. Pretty quiet, but seemed like a nice guy. The young lady dressed how I would imagine a woman of the night would dress for a funeral- ridiculously low top straining against her ample bosoms, fishnet stockings, short skirt. She was a beefy girl wrapped up in a small black dress like a plump sausage. It looked pretty indecent, but I try not to judge.
She ordered a salad and asked if there were peanuts in it. A red flag went up. I told her no and asked if she had a nut allergy because the salad did have walnuts. She insisted that she was only allergic to peanuts and that she wanted the walnuts. I told her I would just put the walnuts on the side just in case.
Well, of course, the kitchen forgot to put the walnuts on the side, and someone ran the plate before I could correct it. I check on them, and the girl is claiming she’s having an allergic reaction in between stilted, heaving breaths. She points a vengeful finger at me, ‘You hid peanuts underneath all the greens!’
I assured her that the only nuts in the salad were walnuts. We didn’t even have peanuts in the building. She said she would try to struggle through the rest of dinner, but each time I checked on them she became more and more histrionic. ‘I thought I was only allergic to peanuts, but I guess I’m allergic to cashews too.’ Tears are streaming down her puffy cheeks. She insists I look at the rash developing on her arm. It was decorated in thin streaks of red, slightly raised, as if she had been scratching it with her fingernails.
The bill comes. I had comped her salad just to make her happy, but they still had to pay for two flat iron steaks and their drinks. Her voice becomes comically pinched as she claims her throat is closing up. She tells me that she has to go to the hospital right this minute, and she can’t stay to pay the bill. She also expresses a disinterest in paying for it, lamenting over and over again, ‘It was supposed to be a special night. Now it’s ruined. I didn’t know I was allergic to almonds.'” So yeah, tacky women fakes a hysterical allergic reaction to get free steaks on her awful date.”
She Never Realized How Much Trouble Her Friend Was In Until This Date
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“I was 22 years old and waiting tables in the evenings for extra money.
Through my day job, I had met this older lady, Betsy. Betsy was ~55 and was clearly pretty desperate for my friendship, and she was so, so sweet, so me and my other 20-something friends took her in. She loved hanging out with us ‘young chicks’ and being a ‘mother hen’ to us. We loved Betsy and were happy to include her, and she was tons of fun, and again, just as sweet as could be. She knew I worked at this seafood restaurant a few nights a week and kept saying she would bring her husband in for a date one night to see me at work. I had met her husband a few times in passing, just a hi/bye when we’d be hanging out with Betsy.
Anyway, one night Betsy and her husband Carl come in and ask to be seated in my section. It was slow and I only had one other table, so I had lots of time to chit-chat and be chummy with them, and Betsy was clearly super excited to be there and show off her young waitress friend, and was done up nice for her husband.
As I mentioned, this place was a seafood restaurant, on a harbor, with amazing, super fresh seafood that was never frozen. Betsy orders the halibut, and Carl orders the burger, ‘medium-rare.’ Being friendly with them, I warn Carl that our burgers aren’t freshly made, they’re actually pre-formed frozen patties from a bag, and that our chefs basically have to cook them to well-done to be edible, and I suggest a few of our other, better red meat options, but he insists on the burger. He’s a bit short with me and I feel kind of awkward like I might have over-stepped some boundaries by suggesting he order something else.
Food comes, and Carl immediately sends it back. ‘The burger is basically a rock! Don’t the cooks know how to make a burger?’ It’s tense and Betsy is clearly embarrassed by her husband.
And when I bring out a new burger, he sends it back again.
Betsy is even more embarrassed and says, ‘Well maybe it’s your fault for ordering a burger at a seafood restaurant! She told you not to!’
With every return, their bickering escalates, and they try to draw me into it. ‘Why do you have to embarrass me in from of my friend?’ ‘Why do you think a teenager would want to be your friend, anyway? Get over it, Betsy!’ ‘This is why I suggested a separation! You don’t respect me!’
So I was basically watching my friend’s marriage deteriorate over the course of the dinner that I am serving them.
At the end of it, I end up taking 20% off their check and packing up some of our famous chocolate cake for them to-go. When I hand Betsy the bag of cake and say, ‘Dessert for you, on me,’ Carl says, ‘It darn well better be.’ Betsy apologizes to me again, and they finally leave. Thank god! Carl left me a $3 tip, which was both expected and still insulting.
I saw Betsy again a few days later and we pretended like nothing happened. All of us went on, friendship-as-usual. And then another week later I see a Facebook post from Betsy and she’s across the country moving in with her adult daughter. We had seen her on Friday night for drinks and she didn’t say anything about leaving, and by Monday she was 2000 miles away and announcing her divorce.
So I’d say that was the worst date I’ve ever waited on. But on the bright side, my friend ended up leaving her jerk husband!”
They Couldn’t Believe What He Was Suggesting
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“I worked at a coffee place (not like a Starbucks, but a small place). It was winter and there was an ice skating rink on the square outside.
At about 3 pm a couple came in, all red from the cold. They ordered 2 hot chocolates and sat down at one of the tables. I make their drinks and take it to them. It was pretty clear it was their first or second date; they were talking about their ambitions and stuff they liked to do, etc. At one point she walks to the bathroom and he catches my eye and gestures something about how hot she is. Since I’m making coffee for other customers I just smile and give a nod so small that it could mean anything. She comes back and they continue to chat. After a while, they order more drinks and a sandwich each. When I’m bringing them over, he looks at me and then at her suggestively. He whispers something to her. She replies ‘What?! Is that a joke?’ He shakes his head. She grabs one of the sandwiches I just brought and throws it at him, then storms off. He looks at me unashamedly – everyone is looking at him now – and asks me if I will suck his junk for €50. I think he’d been trying to talk his date into a threesome.
I said no. He cursed, tried to leave without paying but tripped over some ice skates and knocked himself out on the metal fence around the ice rink.
The girl came back a few hours later to apologise. When I told her what had happened, she couldn’t stop laughing. I ended up going on a date with her myself, a week later, but we weren’t a good match and we kept it at one date.”
First Impressions Are Everything…
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“I worked at the fanciest restaurant in an upper-middle-class suburb. The kind of place where house moms go to get wasted on Thursday nights.
Anyway, one night one of the servers I was working for (I was a busser) points out this table to me and just says ‘Listen in on this table, it’s going to be a long night with them.’ The table had what looked like it was a pair of cousins out to dinner with both sets of parents, so I was originally confused why they were going to be such trouble. I went over to bring them bread, and I could immediately tell what he had been talking about. No one was talking, but they weren’t even looking at their phones, everyone was just tensely staring at each other. It was so palpably awkward I left instantly.
I went about my menial duties for about another fifteen minutes when a conversation at the table finally came up, from the bits and pieces I put together, the two kids we thought were cousin were actually dating, and their parents were meeting each other for the first time.
So basically, a nightmare situation for both kids (who looked about 14).
At some point in the night, the daughter decides she’s comfortable with jokingly calling her boyfriend a ‘dumb jock,’ and, to this day, I refuse to believe that that girl has ever made a bigger mistake. Immediately after the words left her mouth, the boyfriend’s mother loses her mind completely and starts driving into the girl, cussing her out, calling her an easy girl, stupid, and pretty much every single awful thing you can possibly say to a teenage girl. I was pouring water at the next table over at the time and I managed to spill it all over the table because of how loud her outburst was.
The girl and her parents left pretty quickly, seeing as the girl was crying her eyes out and looked absolutely terrified. And, wouldn’t you know it, as soon as they left, the boy and the father turned on the mother and released a near identical stream of vitriol on her. It was so bad I wouldn’t be surprised if they got a divorce.
All things considered, I think that may be the worst date I can imagine for a 14-year-old.”
She Took “Double Date” To An Entirely Different Definition
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“I had a regular sitting at my bar in a chain restaurant about two weeks ago. He sits there for an hour, leaves for 20 minutes or so, then comes 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 except for the fact that she was an hour late, so I continue making drinks for the restaurant.
Couple of minutes later and 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.”
Her “Naughty Girl” Antics Couldn’t Match Up To Beyonce
“So I had a 2 top table with a very handsome young guy and a super attractive young woman (early 20s I think). Anyway, I proceed to go over and greet them and discuss the specials for the night. They seemed nice and it looked like it was their first or second date. I asked for their drink order and the guy gets an ice-tea while the woman orders a glass of white. She then proceeds to tell the guy in the highest pitched voice to order an adult beverage because she will feel ‘so naughty if she is the only one drinking, and she doesn’t want to be a naughty girl.’ This goes on for a few minutes until the guy gives up and awkwardly just orders a mixed drink. That was the first weird exchange. Next I bring them bread and they devour that crap fast. I ask if they would like some more and the woman says oh yes she would love some but she doesn’t want to be a naughty girl again. She described herself as naughty again for another few minutes until I just left. They place their orders and she goes to order a steak with fries as her side. She again repeats how she is so so naughty for getting carbs as her side. The guy just looks so drained by the end of the night because this woman would not freaking stop saying the word naughty. I could tell he was just pushing through because she was wicked hot and apparently a ‘naughty girl,’ but jesus, there is a point where the whole ‘high’ pitched fake ‘I’m a naughty girl’ crap gets so annoying.”
This Manager Knew Just The Right Way To Fight “Hate” At This Restaurant
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“Two women came in on a date on a Sunday night in the suburban bar I worked at. They were absolutely lovely to me, but a table with two lemon-faced older people were scowling at them doing normal date stuff like sharing food and holding hands on the table while talking.
The old couple had a miserable time because they tried complaining to me, and I said I couldn’t do anything. Their mouths dipped deeper and they huffily asked for the manager.
The manager came over (I feel I should mention he did drag on the weekends but passed for straight) and sat there and listened to them (pretty loudly) talk about ‘that sort’ and ‘family values’ and eventually he nodded, said he would understand if they never came back, but he couldn’t comp their meal based on other guests. He leaned in and whispered that he worked at a much better place during the weekend, and he’d comp them if they came by. They agreed that would be acceptable and left. He then dropped two free tickets off at the lesbian couple’s table, dropped the straight demeanor, and invited them to come and enjoy the show. And we comped the ladies’ dinner and threw in free dessert.
The lesbian couple showed up and I hear had a lovely time, the manager said he didn’t see the old people show up but the bouncer said a very confused and then angry older couple showed up looking for a comped meal.”
Her Date Seemed So Terrible He Decided To Do This Nice Gesture
“It’s been years since I’ve waited tables but I remember this one couple. The guy was very possessive over the girl. Every time I tried to ask her anything he would interrupt and speak for her. I don’t know if it was for my benefit or hers but she obviously wasn’t impressed. She kept giving me this kind of embarrassed/apologetic look.
Well, I felt really bad for her so just a few minutes after I delivered their entrees I returned with a glass of red and told her it had been sent by a gentlemen from the bar. I’ll never forget the dude’s expression: kind of furious but ultimately defeated. He never really spoke again and I, of course, didn’t get a tip. He kept craning his neck around though; surveying the dudes positioned around the bar. I wasn’t really worried about that because this dude was a shrimp compared to the guys around the bar.
Thinking back now, I don’t really think it was as clever as I did then. Sure, the guy was a total jerk but I didn’t know him and I could’ve easily sparked something that would set him off later. Scary to think about but the girl seemed delighted with the glass of red. She thanked me and she drank it. Maybe it sparked something in her; like the realization that there were better people out there, who knows.”
Their Romantic Night Turned Into A Tumbling Mess
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“I’d say my worst date would have to be the one where I put my date in hospital.
I was working as a waitress in a restaurant that saw a lot of upscale business lunches–back in the three martini era. The CEO of one multinational used to come through every few months and spend a couple of days taking people to lunch at the restaurant. He was friendly (and pretty wasted by the end of these four hour+ lunches) and he’d often ask me out on a date, quite charmingly, which made up for the fact that he was some 40 years older than me.
After about two years I said yes to a date. Figured it would be a fun dinner and then I’d disappear, dubious virtue intact. We had a lavish dinner in the rooftop ballroom of the Hotel Vancouver. We enjoyed various drinks, lobsters, a couple of bottles, and then several rounds of drinks. There was a big band orchestra playing and, despite the fact that I didn’t know a thing about ballroom dancing, he got me out on the dance floor several times. I was having a great time and so was he.
During the last dance, I decided to try and do the swoop with him in my arms. Did I mention that he was 6′ 4″? Over a foot taller than me. I dipped him down and then I dropped him. And then I fell on top of him. I broke his collar bone. We spent the rest of the evening sobering up in the Emergency at VGH. He kept coming back to the restaurant, but he never did ask me out again.”
The Way This Date Ended Was A Complete Mystery To This Server
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“First time I was ever a waitress was at this fancy restaurant. You know, folded napkins, two glasses on the table, two forks, all that smush.
Valentine’s Day, this couple somehow decided that the 14th would be a great time for a first date. Appetizers roll around, they’re chatting about what they do for a living, which was the dead giveaway that they were just getting to know each other.
I deliver their main course and these two bozos are pretty much on their phones until dessert.
Man gets up to go to the bathroom, takes his jacket. Woman pays for the meal, which I overheard them discussing beforehand anyway because she didn’t want to take advantage of him and was a bit of a nontraditional gal, from what I caught eavesdropping from my other tables. I assumed that when the woman paid and left that he had left too and stood her up. I noticed her leave on my smoke break cause I didn’t see anyone get in the car with her.
Guy comes back, I thought he had left since he was gone for a REALLY long time, and sits down at the table on his phone. Eventually, he realizes that the lady’s coat isn’t there. Then he left with his head down.
Cringed when he asked for the bill and I had to tell him it was already paid for and that the lady wasn’t in the bathroom.
I don’t really know what happened that day. Maybe they both thought they got ditched.”
This Domestic Dispute Absolutely Made This Server’s Night
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“This couple came in, probably late 20s, early 30s. They sit down, I bring them drinks, take their order, all is well and fine. While I’m waiting for the kitchen to finish their food, I hear them start arguing about something. I peek in the dining room and the girl is saying ‘Then show me your phone if you have nothing to hide.’
Oh boy.
So she starts grabbing at his phone and he’s swatting her away, all the while he is clearly doing something on the phone. Shady as heck, right? Finally, he says ‘here fine look’ and hands her the phone. Of course, she calls him out for deleting whatever messages she was expecting to find. Now she’s like in tears, saying she can’t do this anymore, and he’s giving her the ‘baby c’mon stop.’ Eventually, she gets up and walks out. By this point, their food is about ready, so I head over to the table and drop everything off. He’s on his way out the door after her and says they will be right back.
Mhmm.
So naturally, I go behind the counter to continuing watching the show (I work in a pizzeria). They stand out in the parking lot for a few minutes while he tries to bargain with her. She’s clearly not having it. Home girl is getting in her car, she’s ready to leave. She’s fully in the car, ready to pull away when she rolls the window down. I swear, I don’t know what that man said to her, but whatever it was, dude must have been suave, because he gets her out of the car, and they start making out! Passionately.
Maybe they’re just one of those couples that feed on the drama, but they rolled around on the car for a while and eventually came back inside. They sat down like nothing happened, finished their meal, he pays, and they go to leave again. He walks her to the car, kisses the now happy girlfriend goodbye, and off she goes.
Now the super suspect part is after she leaves, this guy hangs out in the parking lot on his phone for another 2 hours, long enough that he came back inside for a slice of pizza. So he’s standing at the counter and I couldn’t help but say something. I forget exactly what, probably something along the lines of ‘So you guys made up?’ He ends up telling me this is his ex girl that he recently got back together with and they’re moving in together. He says she was mad because he was talking to his baby’s mother or something or other. So, who knows. In any case, it made a slow night a little more interesting.
Pretty sure he tipped like nothing though, so screw him.”
