Waiters Share The Worst First Dates They've Seen Unfold

Waiters Share The Worst First Dates They've Seen Unfold

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We have all Witnessed those couples who are on their first date and it is awkward as all heck! Cute, but so awkward. Waiters are one of the only people who get to interact with a couple on a first date, and they are serving us up some juicy first date stories.

Username-Checks-Outt asks:

Servers of Reddit, what's the most awkward date you've seen unfold?

The secret escape

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To preface, I work in a restaurant where we make our own ketchup and some people just don't like it. Fine, whatever, if you're nice I'll bring you the secret Heinz ketchup as long as you don't tell anyone. Anyway, a woman is seated at my table looking super excited and tells me she's on a blind date. She orders a glass of wine and waits anxiously, how cute right? So this dude shows up on his phone, ignores my hostess, and eventually finds this beautiful women waiting for him. He continued to talk on his phone for like, 15 minutes, and when he finally hung up I went to the table. He tried to order for her which obviously embarrassed her, and for himself ordered a well done steak and fries. When I brought it to him he asked for A1 and REAL ketchup. When I informed him we had neither he grunted and said he had ketchup packets in his truck. As soon as he walked out the door she asked for her half of the check and her food to go. I helped her leave out the side door before he could even come back. It was awkward serving him after that. He used 7 ketchup packets.

Major foul

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My first day at my first job as a server at a sushi restaurant (17 at the time with minimal people skills lol).

I had just checked in an older woman possibly in her early 60's/late 50's with a young man who couldn't have been older than 25. Midway thru their meal I went to check up on them asking, "aw, are you taking Mom out today?". They both turned with straight faces and the young man answered, "she's my girlfriend."

I whispered an apology and just peeled myself away

The suspense is killing us

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Date I witnessed

Guy pulls out chair for girl, she doesn't realize what he is doing, awkward pause

Sits down, guy clears throat and starts coughing because he cleared it to hard or something

She doesn't know what to do, ignores him picks up the menu

Waiter comes she asks her date if he knows what's good, he says he'll have what she is having, hands menu to waiter, she orders seafood, awkward pause, he is allergic to seafood takes the menu back and looks for another minute, waiter says he can come back, he says no he'll have a steak, waiter leaves

They sit staring, not quietly looking around or at their phones, staring at each other in silence until food comes which they eat in silence

My gf at the time and i were on the edge of our seats waiting for something to happen

You cannot order for a stranger

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Tinder date. Guy keeps ordering for the girl.

He ordered her drink (liquor) which she corrected to a glass of wine. Then he ordered her some soup, which she stated she didn't want. Then he ordered her meal (shrimp scampi), which she corrected to chicken marsala because she is allergic to shellfish.

She was very sweet and I'm assuming was trying to give him the benefit of the doubt. Until something took a turn and she poured her wine on his head and stormed out.

The one good thing about him though... he tipped the hell out of me. like almost 60% tip on an already expensive meal.

I would kill to find out what he said to make this seemingly sweet girl pour cabernet all over him.

What a jerk!

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It was clearly a blind date. Neither were comfortable at all. Dropped off drinks, both were polite, dropped off food, asked how everything was, the guy rolled his eyes and said "well the food is great I just wish SHE would TALK more". Girl's face went tomato red and I dropped off the check shortly after. Poor girl

Nice and formal

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I once saw a guy shake his dates hand when she reached over to grab some bread.

The most painful meal

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The couple broke up.

He dumped her toward the beginning. Girl cried while giving her order. They finished their whole meal, dessert and all.

When you don't speak your wife's language

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Couple in their 50's came in, husband asked if anyone spoke mandarin, (Chinese restaurant) I brought out the owner. Turns out, they are married, the wife just arrived from China, she doesnt speak any english, the husband didnt speak and mandarin.

The owner ended up sitting with them for a half hour translating...

When a date has chaperones

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I had a teenage couple come accompanied by a parent.

Playing to impress

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Oversaw this waiting for take out at a sushi place.

Around 3ish, a guy comes in and explains to the staff that he was coming in later that night with a date, and that he wants them to come out with a roll and say "hi so and so, nice to see you again, this is on the house"

The waitress gave him the most blank look so he explained the whole thing again, emphasizing how he would actually pay for the roll now.

I should have gone back later to see how that played out.

The ghost third wheel

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We had a middle-aged lady come in with a gentleman. They asked for 3 menus. I went over to the table to introduce myself and ask if they were waiting for one more. The woman said no her husband is here and then the two physically at the table ordered drinks and a water.

When I came back to drop off the drinks her "date" was in the bathroom. The lady explained to me that her husband had died a few years ago and this guy (a friend) kept asking to go out. So she said yes but insisted her DEAD HUSBAND come with them. This is why they had 3 menus. She instructed me to bring her husband up as often as possible, pretend that I knew him and make sure I ask if he's having anything for dinner when I took their dinner order. She would refer to him just as if he was sitting right there. I then heard her tell this guy all night that he tries too hard and he's kind of mean.

I do not miss working in the restaurant industry.

When the drugs kick in and a threesome is expected

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I worked at a nice Italian restaurant a couple years ago. One night a couple came in and specifically asked to sit in my section. I had no idea who they were, but the host said they looked at me and asked to sit there because they "vibe with me". Whatever, so I start taking their order and talking with them, and they were acting very odd. They were being over the top friendly, super touchy feely with each other, and just kind of moving all weird. Finally they tell me that tonight was their date night so they decided to take LSD and come get steak and pasta. I don't really know why they wanted to to do it, but they were nice enough. When they were leaving they tried to get my number to "hang out" later.

When things get crazy before the date shows up

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Used to bartend/waitress at a pub back in the day.

One evening a guy comes in and sits down at a table for two. I go ask him if he want a drink. He orders a drink and tells me that he is waiting for a girl he's meeting for a date to order food.

He waits for a bit and I served him a couple drinks. An hour passes, He's looking at his phone occasionally and drinking. He finally comes up to the bar after an hour and a half, and tells me he thinks he's been stood up.

That's rough man. He orders a couple drinks neat and pounds them back. He's starting to look and sound considerably worse for wear at this point. He ordered a couple more drinks and I told him to wait a bit. He convinced me to get them for him by telling me he was going to drink them and leave. So he downs the drink and get up to leave.

Who should walk in the door as he's turning to go, his date. She was still wearing scrubs and looked pretty disheveled. She apologized up one side and down the other for being late.

I then got to serve one of the most awkward dates ever. He was drunk, like I probably shouldn't have gave him that last drink drunk. They make some small talk and it's terribly awkward. He gets up and goes to the bathroom.

20 minutes go by and he doesn't come back. Finally one of the male servers walk up and tells her that her date is having some troubles in the bathroom. He was sitting on the toilet bawling.

We asked her to get him out of there. We called him a cab and she pretty much shoved him into it and ran.

you gotta do what you gotta do

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I waited tables during college. The most awkward date I've saw unfold at that time was a lady in her mid-30's who got stood up. Like an hour in, she was still waiting and drinking her 3rd glass of wine. It was really sad to see her come to the realization that her date stood her up. But by that time, she had 3 glasses of wine in her and she ordered food and just talked with random wait staff from time to time and I'm fairly certain ended up convincing one of the waiter who was getting off his shift to go home with her.

Watch the shoes

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Probably the one where the guy's choice of footwear was such a turn off that the woman didn't even sit down with him. She left before he even saw that she came in.

What a pig

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I was not a server at the time BUT .... My boyfriend and I went out to dinner one night and sitting directly in front of us was a middle aged man wearing basketball shorts, a t-shirt and flip flops with socks. He had ordered himself a large appetizer and was drinking a beer. Five minutes later, this younger, attractive , very nicely dressed woman came in and sat with him. You could tell by the look on her face that this was a first date and not was she expected. By this time, he had already ate most of the appetizer and was very loudly talking about how tiny her body was and how he's a big man that likes to be in charge. We felt terrible for this girl! She was very mousy and seemed too sweet to say anything. He kept trying to get her to take shots with him and then was commenting about her having to crash at his place. It was time to leave so we made the bartender aware that the girl look to be uncomfortable.

Worst case scenario

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I once was a server at a very upscale French restaurant in NYC. One evening a middle-aged man and a young woman are sat in my section, clearly on a date. You could tell this woman was his mistress by the way they interacted with each other. They were high maintenance but pleasant enough. Right after they had received their entrees, the man looks across the way to another table and loses all the color in his face. His date noticed and turned to see what he was looking at. The mans wife was at another table, also on a date with her side piece, on the other side of the restaurant. The wife sees him and has the same expression on her face, which very quickly turns to rage. She briskly walks over to his table and starts whisper-yelling at him, pointing her finger right in his face. He starts to do the same back at her. This isn't a very big restaurant, everyone knows what's going on and the atmosphere gets icy. The mans date is just staring at her plate, absolutely mortified. The wife's date pretends nothing is happening and continues eating. Eventually, the wife storms back over to her table and wolfs down her dinner (no exaggeration, she was like rage eating). He sits down and his mistress won't speak to him for the rest of the meal. This is a fine dining restaurant and they ordered multiple courses. Having to clear, crumb, and reset their table two more times was less than fun. He left a very big tip and apologized on the way out.

The hit and run

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Not a date but the end result was the guy paying for the girl's meal and drinks.

VERY chatty woman in her early 20's was at the bar and ordering more than a few drinks, probably 5 or 6 cocktails and a few beers. Did I mention this was the middle of the day? Guy sits next to her and they end up chatting, good for them. It's time for her to leave and she hands me a credit card which is of course declined. She apologizes and fishes around for another credit card. This one is declined as well. She gets a little pouty and plays the woe is me card. White Knight next to her swoops in and says not to worry, he'll pay the bill, which is around $100. I guess he was expecting to get some and take her home, but as soon as he paid and the card went through she fast walked out of the place and was never seen again.

The first fight

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In high school I worked as a buffet attendant/ waiter because the waitstaff sucked and I would end up getting people their drinks and even taking orders on occasion. Anyway a man and woman come in and I take their drink order. I somewhat recognized the woman as the mother of a guy from my high school and I know his parents were getting a divorce and well about 5 to 10 minutes after they arrived I see the soon to be ex husband storm in and he and the date get into a fist fight in the middle of the restaurant. It was a bit late so it was not as full but it basically shut Down the restaurant for about an hour because of all the cops and stuff.

This man is a liar

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I was a server at a place that had a special for "all you can eat riblets", this was in some time in 2000. Man and woman come in, get seated in my section. Dude was a little dingy, looked to be in his early 30's, she was much better put together, I guessed late 20's. Got orders, drinks, they both did the riblet thing, they spent about 3 hours there. During that time the guy also asked me about how I liked working there and if we were hiring for kitchen help. I got him an application and he filled it out. While I was giving it over to the manager they tried to leave. They managed to get to their car, they even would have managed to get away if the battery wasn't dead. My manager and I went out to give him his bill, he explained he didn't have any money, so my manager started to call the police. His date stepped up and paid for the bill and gave me a heafty tip. She said he had told her he'd already paid while she was in the restroom, didn't really believe her, but it didn't matter much. She called for a cab after that, the guy was still trying to start his car at 11pm when I left.

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