Have you ever been to a restaurant? Yeah you have! And since you have, you’ll know about these people called servers.

Do you think they hear what you say and just ignore it?

Think again my friends.

No, there’s not a ton of upsides to being in the service industry, but maybe this is one of them?

Waiters/waitresses of Reddit, what’s the most awkward first date you had to witness first hand?
byu/Flavor_Town_ inAskReddit

You can certainly get some good stories out of it. Like these Redditors did:

1. “More sad than awkward”

More sad than awkward, but here goes (for context, I am a woman in a long-term relationship and was NOT hitting on the girl or anything) : One day this (very cute) 20-ish girl comes in, orders, and cheerfully asks me if we have any boardgames that are great for two people (I worked in a concept bar where we had 700+ boardgames you could play as long as you ordered something to drink). I show her a few games, she choses one and sits at a table near the entrance.

30mn later, she comes and sadly asks me if we have any games you can play alone. I give her one and tells her if her date doesn’t come, I’ll give her a free shot.

Another 40mn later, she comes back, I give her the shot and we talk a bit, then she goes back to her table to play by herself (It was a busy night, overwise I would have played something with her, she seemed nice and was obviously sad).

The guy ended up showing up almost 2hours late, ordered a bit rudely, she paid for him, and they spent less than an hour talking. He wasn’t interested in playing a game and didn’t really seem interested in his date either. He left early, she stayed a bit to talk with me as I started to clean up, I offered her another shot and drank one with her, and she left all sad.

I imagine she was excited for her date and thought the boardgames bar was a cute, fun idea for a first date, but the guy was so rude being late and not showing any interest… just sad. She came back a few times with friends though and was really a nice girl.

– Grog_Bear

2. “Super weird chemistry”

Didn’t happen to me but I was working while the bartender got to experience it. Guy and girl came in, super weird chemistry all night.

The guy is obviously trying to impress her by being a huge douche and she looks like she’s just pretending to not hate it so the date will end faster.

At the end of the night, she says she’ll take an Uber home and he awkwardly leaves without her.

She then waits for the bartender to come back over, orders another cocktail, and asks for his phone number.

– BigFuturology

3. “Not a single person noticed.”

Not a first date but we did have a guy come into our steakhouse on a Saturday night at 7 pm with NO RESERVATION.

He then told us on the spot he was going to propose to his girlfriend. We had to seat them somewhere awful, it was right next to the bathroom and when he got down on one knee, looking around nervously, absolutely no one noticed.

Him and his gf kept waiting for the rest of the restaurant to see them and go quiet or even clap for them but not a single person noticed.

She said yes, looked disappointed and they went back to dinner like nothing happened.

They must not have minded too much because they came back for their one year anniversary, this time he made a reservation lol!

– sophiegitt

4. “I saw him take the powder out.”

I legit saw the guy try to roofie the girl.

Like not even trying to be hidden about it. He did it right in front of me.

The girl went to the bathroom and I was cleaning the table next to them.

I saw him take the powder out and slip it inside the drink.

Another thing too, it was a pizza place. Who tries to roofie someone in a pizza place!

– tottaly_not_masters

5. “Dine and dash.”

Worked at a pub connected to a brewery in college.

Dude comes in with a stunning woman, I mean she’s absolutely gorgeous. Whole time they’re sitting at the end of the bar, and you can hear the guy talking about how he has a room for them next door at the hotel in downtown.

So they decide to go to the brewery next door, gonna pull a little dine and dash. They got over there and didn’t realize we are on the same system, so he orders a couple of beers, and the bartender on the brewery side asks if he wants to add it to his tab. He looks over confused and says “what tab? I’ve never been here.” She prints off the restaurant bill plus his brewery tab, it’s like $80 or so. He just blankly stares at the poor bartender, flies off the handle.

The girl he was with ended up paying for it. They walked across the street and to the hotel, he has already invited her up, she stalls until her Uber gets there and then just dipped out.

Kinda funny, kinda awkward, but that’s what you get for dine and dash.

– stocky_stegasaurus


I used to work at a sushi restaurant in Anchorage, and there was a girl who would come about once every few weeks with a different guy. Every single time, she ordered a heodubbap, which is like a rice-salad-sashimi bowl, and it was GIANT. I’ve only ever seen a handful of people ever finish the entire thing in one sitting.

She would finish the whole thing (with CHOPSTICKS) and always ask for a spoon towards the end. It was always fun watching the guys look stunned when she finished.

One day she came with this dude that ordered what she did, and when they both finished the bowl, they ordered another and split it.

Wish they had ended up together but she came back with a different guy a couple weeks later.

– themerrypaek

7. “Soon to be former friend.”

A couple was shown to their table, and the guy was on the phone the entire time. I normally wait until guests are off their phones to give my spiel, the specials and such and take a drink order, but he didn’t show any sign of getting off the phone. I take the order, which the guy just holds his hand over the phone, talks over his date.

When I come back, she attempts to order an app, our house specialty, and he tries to say the portions are large enough without. She orders the zucchini anyway. I get the dinner order, and bring out the app. At this point, I hadn’t been to the table when he hadn’t been on the phone.

While I was putting together the salad, the woman comes out to the lobby and asks to get her meal packed up. She ended up paying her half of the bill and ducking out. She told me this was their first date and she was set up by a soon to be former friend. Said she was going to be calling her friend as she walked out. When I brought the guy’s meal to him, he asked where her dinner was and I told him what happened. He really thought she was in the bathroom……

– newguy1787

8. “Never saw them again”

Not a first date, but a last date. We had a guy who would bring his secretary in for lunch three times a week. Our per person average at lunch was $125. Everyone knew he was married because he’d bring his wife and kids to dinner three times a week (at $200 per person average), often on the same day.

Well one day he realized he needed to dump his secretary. He did it at our restaurant. We all watched it happen too because she started crying SO HARD, and they were center of attention for everyone to see.

To make things weirder, he did it early in the meal and he drove her there. So she came and hung out with the employees until his lunch was over, acting like everything was totally fine even though her tears were welling up with every word.

He was back in the restaurant with her within a week. Then we never saw them again. Never again with the wife and kids either. Always wondered if he got caught in the end.

– turboiv

9. “Leaving hungry”

I was working at a high end steakhouse when a couple comes in on a first date. The man was really friendly and seemed like he knew his wine. He orders a nice and fairly expensive bottle.

As I’m presenting the bottle, the woman’s phone rings and she answers. Apparently, her close friend just broke up with her boyfriend and is distraught. The woman asks if her friend can join them for dinner. The man says “of course” and is really gracious about the whole thing.

The friend shows up within a few minutes and is a crying, hot mess. I bring the friend an empty glass and before I can pour it, the first woman grabs the bottle and fills the glass to the brim, then requests another bottle. After I open the second bottle, the man excuses himself to the restroom.

While he is away, I overhear the friend expressing concern about the menu prices. The first woman then says “Get whatever you want, I’m not going to ever see this loser again.” So then I catch the man coming out of the bathroom and tell him what I just heard.

He says “What do I do?” I tell him he is welcome to leave through the delivery door in the back and I will play dumb for his date. The guy expresses his gratitude and slips me $100 on his way out.

The woman becomes increasingly irate as the night goes on and she realizes the man isn’t coming back to buy them food. She waits until closing time before settling the alcohol tab and leaving hungry in a taxi.

– kelpat14

10. “Keep our mouths shut”

Not a first date, but very awkward: guy comes in with an escort and drops a good amount of money on booze at the bar.

Then she leaves a few hours later, and he informs us that his wife is on her way to meet him for dinner and tips us an extra $200 to keep our mouths shut.

Keeping it classy!

– InellPalmisano

11. “Maybe 10 and 12”

Not a waitress, but my daughter and I were having dinner at a restaurant and the table next to us was a mom, dad, and two daughters, maybe 10 and 12.

The parents took them out to dinner to tell them they were getting a divorce.

– The_Petty_Spaghetti

12. “My idiotic, high blunder.”

Once, as a high school teenager, while waiting tables at a now defunct make mexican restaurant chain (think applebee’s, but tacos), a first date came in. They seemed unable to converse. It was super awkward. Painful to watch.

Well, at one point the woman asked for a refill of her tea. I dutifully went and got the pitcher and came back to fill her glass. While pouring, i literally dropped the entire pitcher, a full gallon, of sweet, sticky tea directly onto her. It went down her shirt. Her skirt. It was everywhere. She was completely and utterly soaked.

My newly blossoming career as a server flashed before my incredibly stoned eyes. I apologized profusely. I brought her out like 4000 napkins. Her date was dumbfounded and probably thinking “didn’t think this could get worse, but here we are”.

Well, she cleaned up the best she could. And they ate their meals. And, magically, they began talking. They started looking at each other like a new couple looks at each other. They laughed. They enjoyed their sh*tty food. She dried out.

They left the restaurant an hour later, with her arm in his. They gave me the biggest tip I had ever gotten. I got $20 on a $20 bill, in 1996.

Somehow, my idiotic, high, blunder, turned the worst first date ever into the best first date ever.

I like to imagine them now as happily married, parents of 7 lovely children, who love telling the story of the moron who poured an entire gallon of tea on her, 25 years ago.

– AmishTechno

13. “He got up.”

Not a 1st date but a guy decided to propose to a stripper from Scores (high end joint in NYC), she was stunning.

Also in fine dining, he gets on one knee and pops the question and she goes out loud “are you f*cking kidding me”.

He got up and asked for the check.

– Pieniek23

14. “Awkward silence.”

A middle aged couple.

Man: [30min monologue about the cars he likes, how fast they are, what the challenges are in maintenance. He was literally going on non-stop every time I pass them]

Me: [arrives with food which made him shut up for like 10 seconds]

Woman: [taking the sudden silence as her chance to get a word in]

Woman: Well, I really like butterflies.

awkward silence

Guy: [continues his car talk until dessert]

Curiously enough they came back two more times over the summer…

– Sweetholymary

15. “That cursed seat.”

I worked as a barista at a coffee shop with a dish washing sink that brought you face to face with whoever was sitting at the coffee bar across from you.

For some reason, so many people chose this spot for their first dates, so I would have to wash dishes and pretend I wasn’t literally on the date with them.

One time a person I knew was on their first date with someone and chose that cursed seat across for the dish washing sink.

Because we knew each other, we chatted a little bit and then as if a partition raised between us, they began their date… but I still had dishes to do….. So f*ckin uncomfortable.

– maybemaggot

I’m so uncomfortable right now I might just crawl out of my skin.

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