If you work in a service restaurant, one of the easiest ways to pass the time is to become a professional people-watcher, and some of the scenes you see unfold are truly remarkable.

That’s why I’m excited about this question asked on Reddit:

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

Check out these crazy date stories courtesy of the servers of Reddit.

1. “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

3. “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

4. “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

5. “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

6. “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

7. “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

8. “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

9. “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**king kidding me”.

He got up and asked for the check.

– Pieniek23

10. “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

11. “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**kin uncomfortable.

– maybemaggot

12. So high end.

I worked at a higher-end restaurant as a busser for a while, and eventually was given a chance to serve in the bar area while a jazz band played. Most of the tables were just drinks and appetizers.

My first shift a woman in her 40s or 50s came in with a tall, dark, and handsome guy no older than 30. Nothing wrong with that in my eyes, but all of my interaction with them was the woman talking down to me on some sort of power trip (maybe to prove to her guy that she’s an alpha female or something, dunno) and her ordering everything for her date. They had cocktails, ordered a bottle of wine, and had a couple entrées.

She ordered ahi tuna, RARE. She was very insistent on the rare, so much so that I put blue rare into the computer so everything would be fine. She sent back 4 separate plates (all too well done) to the absolute horror of her date. I informed her after the second that they wouldn’t be taken off her bill, and she scoffed and made some comment about how she’s loaded and it doesn’t matter.

After the four plates, she sent the last one back and asked for a shrimp cocktail instead. I left them to enjoy the music, brought the check, and when I came back to pick it up, her date was gone, and I don’t mean, went to the bathroom or went for a smoke, all of his things were gone and he was nowhere to be seen for 30 minutes.

She apologized to me and asked if I could take the ahi tuna (~$45 each) off of her bill. Told her to pound dirt. Not really, but my manager did.

Next day she wrote a 500 word review about me, using my first name, on the restaurants Facebook page. My boss printed it out, framed it, and I still have it today.

– IDKimjusttheintern

13. Cool down, you two.

A teenage couple sharing an ice cream and holding hands very awkwardly.

After they finished the ice cream they kept talking about their – very adventurous – sexual fantasies.

They were around 14 years old. Super awkward to have to interrupt them to ask if they want anything else.

– Ashley_42

14. That’s not good.

I had these two people that were there on a first date.

After the appetizers this poor man was going back and forth to the bathroom all night. There was only a few other people in the restaurant at the time so it was noticeable and they were chuckling everytime he got up. I honestly felt so bad for the guy.

– RAM_592

15. The mix up.

At a restaurant i worked at, there was a white guy and a black guy on a first date. They were sitting in a booth and having a good time.

White guy gets up to go to the bathroom. When he came back he sat in the wrong booth with a different black guy.

Took him a minute to realize it was a different person. The person he was on a date with was not happy at all.

They tried to salvage the date, but it didn’t work.

– Bluegunder

16. Dine and dash.

At the end of the dinner, 2 couples on a double date dine and dash. I chased them down, and the girls had no clue, their dates had told them they already paid.

The girls ended paying, the guys had no cash.

– joellyy

17. Obviously stood up.

Not a first date, but when I first started bartending I had a woman who was very obviously stood up.

She got there, ordered a drink, and would look around every once and awhile. I saw her use her phone a couple times and her mood just got sadder until she finally put her phone upside-down on the bar and ordered food an hour later.

I wiped what I could off her bill then paid the rest myself, told her it was on the house. In my career it’s happened two more times, once with another woman and once with a guy. I did the same thing. Nothing sucks more than eating alone and defeated.

– fraxiiinus

18. Outta cash, outta time.

The guys card declines. I didn’t want to embarrass him so I waved him over near the credit card machine so it would look like he needed to go to the bathroom. He told me to try it again and I assumed he was going to move money over on his app.

He went back to his date. Card declines again. The machine prints a receipt that states the reason for decline… “insufficient funds”. I keep trying 4 more times. I go over to the table and say “I’m having an issue with the card, might be our machine, do you have another?”

I walk away with the new card, and it declines. I wave him over. He gets up angrily and I’m guessing now the date has caught on. He proceeds to berate me saying that it must be our machines because HE KNOWS HE HAS MONEY! He starts making fun of me questioning if I know what I’m doing. He is doing this in front of his date I’m guessing to save face.

Gives me another card. Declined. The date pays….

– justacomment12

19. Love me Tinder.

I worked at a bar where like 50% of our business was from Tinder dates.

This one time, two guys came in separately and sat at different tables by themselves, along the same wall. They were both facing the door and clearly waiting for dates.

Eventually a woman comes in, walks up to the closest guy, sits down and they start chatting. They start ordering drinks. After ~5 minutes, the other guy, who is still waiting by himself, gets up and walks over to the couple. He says ‘hi’ to the girl and is like ‘um aren’t you so-and-so? …I’m so-and-so we were supposed to be meeting?’ She was clearly flustered, lots of awkward laughter, and she gets up and goes with the other guy to the other table.

Couple minutes later the other woman shows up and sits with first guy and he tells her all about it. Lol

– frankylovee

20. Craigslist personals.

Lady comes in to get a table says she’s expecting a man and gives us a brief description. He shows up about 10 minutes later and she starts saying she knew it, he looks very surprised and scared. I took a drink order and when I get back they are gone.

The hostess fills me in that in my absence they had a heated but civil exchange, the man was married to the lady’s cousin also the lady was married.

Apparently they had been texting for a while after meeting via Craigslist personals. I’m assuming the married but looking section. Don’t known if they hooked up in the end or just called the whole thing off.

– Hazmatt40oz

21. Let them not eat cake.

In short, he got there early and let me know it was a first date which was a lunch date.

When she got there they started chatting and he ordered a drink and she ordered a water. After a few minutes he skipped on appetizers and every so often I would go by to see if they would like to order. She would open her mouth to speak and he would interrupt with something like they were fine at the moment.

Well this went on for a while, I even tried to just take hers but he would insist they were okay for now. So he kept ordering drinks and she kept sipping water. After an hour or so she said she had to go and just left.

He asked me if he did something wrong. I answered honestly with “since it was a lunch date she probably didn’t have too much for breakfast and if you offer a lunch date she’s probably expecting to eat and you wouldn’t allow her to order, she’s probably starving” he sat there and drank till the end of my shift.

Super awkward

– PrivateRyGy

22. The label debate.

The guy starts talking about how nice it is in the modern day that you can just date without labels.

Woman, in suspiciously chipper voice responds that sometimes labels are really helpful in defining the boundaries of the relationship.

Man, very upbeat replies that SOMETIMES it’s nice just to enjoy your time with someone without having to define anything… it was so hard to listen to!

– Swims_with_T-rex

23. Started off great…

The date I saw started off great . . .

I was playing in a band at a small club. There were about 30 people in the club. A couple who had been sitting close together in a corner booth disappeared together into one of the bathrooms.

In between songs, when it was quiet in the club, the bartender yells, “They better not be in there f**king on my sink!”

The whole place turns and stares at the bathroom door, and as we’re staring, the couple emerges, smiling at first. Then they look around, see everybody staring at them, and their faces turn a deep color of shame.

They quickly paid their bill and left.

– ThatGuyFromOhio

24. The Valentine’s incident.

I used to work at a Mexican restaurant and one year when I was working on Valentine’s I was subject to one of the weirdest first dates ever.

A couple walks in, she is dressed to the nines, like she’s ready to hit up a club. He is dressed more casually, in jeans and a button-down. Our hostess seats them and when I go to greet them the man announces that this is their very first date! The lady looks less than impressed and gives a small smile, more like a grimace. They order drinks and as I’m watching their table you can tell that the date is not going well. The guy is talking animatedly and the girl is glancing around like she’d rather be anywhere else.

I head over to take their order and it’s clear that I’ve interrupted something. The guy looks a little embarrassed and sad and the girl looks p**sed off. He orders his meal and she flippantly orders something (seafood enchiladas) without really looking at the menu. She tosses her menu in my direction and sucks down the rest of her drink. Okaaaaay then.

I deliver their food and go back behind the counter to continue rolling silverware and watching my tables. They dig in and the man seems to be enjoying his food, his date looks disgusted and is flicking bits of her dinner around the table/floor. I walk over to check in and see if she maybe wants to order something else. I get to the table to ask how everything is and she gets up, SCREAMS that her food is DISGUSTING, and goes OFF about how s**tty this date was. She started yelling at him about how he should have ordered for her, how dare he take her to such a low-class place, she was so done with this, blah blah blah.

She shoves her plate away, gets up, and storms out of the restaurant. The dude is mortified. I tell him I’ll be right back with the bill and would he like his food boxed up? This f**king guy shakes his head, pulls her plate towards him, and says nope, he’s fine to continue eating the meals he’s paid for.

He stayed for the duration of his meal. I never did find out what happened to the lady. We talked about that incident for WEEKS after!

– TheTrickyLettuce

25. Old flames.

I was the one on the first date.

Went to a bar with this guy, our waitress came up and immediately recognized him, was super friendly, took our orders and left.

While she was gone he told me they used to date. The rest of the night they openly flirted with each other.

There was no second date.

– 1927co

26. Wrong tree?

Saw a guy hitting on a girl and buying her drinks for the entire night, then realizing she was a hooker.

– ViperKira

27. “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 board games that are great for two people (I worked in a concept bar where we had 700+ board games 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 board games 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

28. “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

29. “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

30. “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

And that’s just scratching the surface.

What have you seen/overheard at your job?

Tell us in the comments.