Waiting tables isn’t a career for everyone, but many of us have done it at one time or another. For me, it was a great gig for several years of my life, and I can verify the people watching opportunities are hard to match.

These 17 servers saw things on Valentine’s Day that they won’t soon forget, and thanks to Reddit, neither will you.

17. Here’s where you can find him.

Not waitstaff, but I used to work Front Desk at a hotel. One Valentine’s Day I was working the night shift, and this woman comes down with a cut above her eye looking like she just went a few rounds in the ring with a boxer. Woman starts sobbing and asks us to call the coos which we do immediately. Turns out this girl’s boyfriend just beat the shit out of her during a fight, and from what I could tell this probably wasn’t the first time.

So after the cops show up and haul the dude off, my manager offers her a different room on comp as we need to leave the guy’s stuff where it is for him to pick up the next day. She accepts, and I go up with the woman to help her collect her stuff and move to the new room. There were a bunch of bottles of alcohol in the room, and she donated them to the front desk staff. I got a bottle of Hypnotiq, and some vodka. Manager got a bottle of Patron.

Cherry on top of everything, the dude’s wife called later that night saying someone had stolen his card as he was out of town on a business trip. Never one to defend an abuser, I told her where she could find her husband. Fun times.

16. And obviously they lived happily ever after.

I blew my cars tire and my friend came in to bail me out. Were both straight dudes and forgot it was valentines. Decided to have dinner and both were coming from important meeting so had suits on.

We didnt catch on until the end on how the entire wait staff thought we were just the cutest gay couple.

15. His mistake.

I was a delivery driver for a fruit bouquet company and I had two arrangements from the same guy.

Routes were made for me and the truck was loaded so there was no way I could mess this up. Delivered both arrangements to the appropriate address.

I headed back to the store to find the store owner and the guy who sent these in an argument. This idiot put the wrong name to the houses. And it was on the card with the arrangement. Along with the phone numbers. So both women called each other and then called the guy. He tried to say it was my fault. Then the person who took the order. He ordered it ONLINE. All we did was import the order.

I hate valentine’s day because of that place but man was that great.

14. What a jerk.

I served at a Japanese hibachi restaurant and once had a couple come and the dude dumps her after the meal. She then gets up and throws up a trail probably a good 20 feet as she runs to the bathroom.

The dude got up and left the girl and I was left to clean the mess.

13. It was not going to end well.

I had a section one V-day that had a marriage proposal, a 40th anniversary, and a break up all at the same time. The break up was the worst. The guy brought his high class date a gift; a mini ceramic bear holding balloons.

He presented it when I was at the table and she looked at it like it was a hot turd. I just knew this was not going to end well. She left at the end of the meal and must have said something because he stayed at the table for another 40 minutes, head down and crying.

I felt bad, he saw the celebrations going on at the other tables.

12. Oopsie.

There was a note in our reservations that it was an engagement, they wanted champagne, a specific seat, bunch of other stuff. The server comes up to the table with something like “so I read we’re celebrating an engagement, congratulations”.

Confusion from the woman; glaring from the guy. He hadn’t proposed yet. She ruined it.

11. A sweet one.

This was relayed to me by a close friend

Older Woman, probably in her upper 90’s with her teen-aged grandson at a semi classy restaurant. She was dressed to the nines and the grandson was in a nice button up and dress slacks. As they got seated at their table the grandson placed a framed photo of what my friend assumed was the boys grandfather and husband of the older women.

​ Found out it would have been their 70th wedding anniversary but he had passed suddenly but peacefully a few months back. The grandfather had always wanted to take her to a nice restaurant but never had the time or money to do it. So the grandson saved up his pay from the last couple of months and even got some donations from other relatives and took her to the restaurant. They ate dinner remembering all the good times with the man. They had my friend to take a picture and she did. They tipped my friend very well.

​ By happenstance my friend ran into the young man some weeks later to find out the grandmother passed away a few days after that night, peacefully in her sleep holding a photo of her beloved husband. He was so happy he could make that night special to her. Said it was the only day he saw her smile since his grandfather passed away. He got the picture they took at the restaurant printed in wallet sized and carried it around with him in his wallet.

10. That’s a rough night.

These two were on a date and the guy went to go use the bathroom, The girl just up and leaves after he went to the restroom.

When the guy came back he sat around for awhile until asking his waitress where she went. She replied with saying that she left. The guy then asked the waitress if she would go on a date with him.

The waitress said no.

9. It didn’t last.

Not a waiter but I was a pastry chef at this big resort in cape cod. We got a special order from this guy who was coming in for his anniversary ( Valentine’s day). He wanted his desert to have “Will you marry me?” written on it so he could pop the question when it came out.

He called ahead to the front and back kitchen, even came in himself that morning to make sure it was good to go. The whole crew was behind him. We had cooks all night coming in the ask if it had happened yet. I wrote the inscription on the plate and dressed it to the nines with gold leaf and expensive chocolate.

I’m taking a picture of the plate just before it’s set to go out and notice our head waiter come in with a weird look on his face. He says plainly “They don’t need it”

She broke up with him before the entrees hit the table.

8. She’s just not that into you.

Not a waiter, but in my strip club bouncer days we had one of our regulars get suited up and bring flowers in one V-day to try and woo one of the dancers. It did not work.

Pro-tip: If every time y’all hang out it involves you giving her money, she is not in to you.

7. Bless his heart.

A guy did a backflip and asked a girl to be his valentine… she declined.

I walked up to him and asked if he was fine, he said it took him a week to perfect.

6. Dump in private, please.

They came in at lunch the day after, so it was pretty empty but it was still for a Valentine’s Day date. They were both pretty nice at the beginning, the guy asked for a picture and whatnot.

As the meal went on, the dude got progressively drunker and by the time I brought the check out, the woman was gone.

When the dude gave me his card, he said “I’ll give you a bit of advice. If you’re taking a girl out to break up with her, do it at a McDonald’s and not an expensive restaurant”.

5. Poor guy.

I was eating in a fine dining establishment (Chili’s) several years ago. In the next booth was a really young guy who had a big bunch of roses on the seat next to him.

He kept looking at his watch, looking at the roses, and popping open a ring box for a peek at the ring.

He did this for a half hour or so, then began calling and texting someone (presumably his girlfriend) over and over.

As we were waiting for our check, he hands my wife the roses, mumbled something, and walked out.

Poor guy.

4. Oh man that’s rough.

He proposed, she said no. He cried and tried to change her mind for 20 minutes while she sat there stony-faced.

She finally got up and walked out. He paid and left in tears.

3. Sometimes it doesn’t work out.

Had a couple sign divorce papers and cry a bunch.

2. Do not serve this man.

I worked at a pretty high end Mediterranean Bistro, my second Valentine’s there it was probably the busiest night I’ve ever worked as a server. We had reservations that booked basically the entire restaurant including the bar and patio from 4 P.M to 11:00 P.M. No walk-ins were to be seated unless a reservation was cancelled, or someone with a reservation didn’t show up.

Most of the customers were pretty understanding and either waited or simply left. One dude however kept pushing and pushing asking every 10 minutes how much longer until he is seated, constantly saying how he is a regular customer; and how his date is going to be there at 7 (he got there at 6). We insisted that once a table was available, and all the customers before him we’re seated, he would get a table, but because the amount of reservations we couldn’t guarantee he would even get a table at all. At about 6:50 the guy loses it, fast-walks up to the hostess stand where the reservation book is, grabs the reservation book and practically runs out the front door.

Now everything is going to complete shit because the only copy of the reservations for the night that is barely half over is gone. Two of the owners ran outside to follow the guy and try and get the book back, but by the time they got out he had already left the parking lot. Even better is, two hours later, chaos is still running rampant and the dude shows back up saying he has a reservation for two. Three of the five of the owners (all brothers) escorted the dude and his date out to the parking lot and banned him from the restaurant permanently. They even took a picture of him and posted it in the window saying “Do Not Serve This Man”

TL;DR Salty dude without reservation steals reservation book and then tries to come back later

1. A few good ones.

16 years in hospitality gives you some good stories.

The most awkward:

My first job as a waitress a guy wanted to propose to his girlfriend. He came in 2 months before to book and had everything figured out. He planned to pop the question during dessert. We had champagne, balloons and sparklers prepped for the big moment. The time comes, he drops to one knee gives a speech about his love for her. He asks, she says no, puts the ring in her bag, finishes her dessert and leaves. Quite possibly the most awkward thing I have had to witness (alongside around 200 other people.) The manager gave him everything for free he felt that bad for him. Cringed inside every time I saw him after that.

The most fucked up:

I was working as a duty manager and one of the tills kept dropping off the network. As I was trying to fix it I could clearly hear the conversation of the table by the waiters station. It started out sweet enough with her excitedly telling him she was pregnant. He went quiet and didn’t say anything for a bit and then asked her what the plan was. She said she was keeping the baby. He said he didn’t want kids and had told her this. She got upset and said she thought he’d be happy and change his mind when he found out. (By this point I’ve fixed the till, but am unable to step away from this car crash.) Turns out she stopped taking the pill without telling him thinking she could turn him around. He said he knew she could be a little nuts sometimes but this was next level. He told her it was over and she could send someone to collect her things as he wanted nothing more to do with her. He called me over to pay the bill and just left. The guy never even shouted, he just calmly went fuck this and noped out of there. I couldn’t even look her in the eye, just left her to leave in her own time.

The funniest:

Managing hotel room service where there was a valentines package that included getting each course of the special menu delivered to your room. More than a few couples thought it was a good idea to call for the next course and then start having sex. Having to help with deliveries as reception fucked up the bookings; I had the ‘privilege’ of people answering the door naked, seeing sex toys strewn around and one where the other members of the threesome were carrying on in the background. After complaints of similar instances from my team I had to take action. I ended up having to call the offending guests and tell them if they could not respect my team by answering the door in at least a closed dressing gown they could come down and collect the rest of their meal from the restaurant. Bonus from the same night: had to call an ambulance for a woman with a dislocated shoulder. The guy admitted that they were trying to recreate a bukkake type scene in the shower using conditioner as the ‘cum.’ He slipped in the conditioner and fell on her.

Y’all, these are priceless. I would not have been able to contain myself.

People are just out there providing free entertainment!