Restaurant Servers Recount the Most Awkward Things They've Ever Seen


Any time you have to help someone else, it can turn awkward real quick. Like when a friend asks you to help them move into a new house -- or a threesome.

Potential for awkwardness is multiplied when you're a server at a restaurant, because however weird things get, you've still got to grin and bear it and refill that glass of water, all while ignoring the homeless woman whose breasts are leaving smudges on the window. To highlight how uncomfortable things can get in the line of fire, we asked a group of restaurant veterans to share their most awkward stories. And yes, said stories include threesomes and homeless nudity.

Flickr/Heather Katsoulis

The tempranillo gave him away

“A man walked up to the bar, and one of the servers told me he'd been in last night drinking the tempranillo. So I asked him if he'd like to try that wine again, and the woman with him got really angry. Apparently they were on a first date, and he'd said he hadn't been here in a really long time, but had obviously just been here with another woman. She ran off to the bathroom, and there was another server in there who suggested she just shrug it off, let him pay for the meal, and forget about him. She came back to the bar and ordered a $100 bottle of wine.”

Get divorced, get free wine

"I watched a couple get divorced once. It was after lunch service, so no one else was there. Just this couple. They were on the other side of the glass on the patio, so they didn't realize I was just standing there. They were arguing and getting really emotional. Finally she slid some papers over and he signed and then ran out. She just sat there and drank a glass of wine and ordered another. We comped her wine and she left without saying a word.”

Perverts like cookies too

"When I worked at a cookie shop, someone once put in special instructions to bake them without any pants on. When the dude came in, he looked like such a perv."

Flickr/marissa anderson

Anniversary ruined by boobs and a dead squirrel

“At an unnamed high-end restaurant, I was waiting on a couple celebrating their anniversary. They were seated in the VIP table, which is at the window on ground level. In the middle of my introduction, a topless homeless woman came up to the window to show the guests her pet squirrel, which was dead and wearing Mardi Gras beads. Nasty saggy boobs and roadkill are obviously the best appetizers.”

She drew the line at panties

"I was waiting on a group of three adults -- two females and one male -- who were clearly on a group date. When they ordered their drinks they told me that with every course I brought out they wanted her to tell me a naughty story, and then asked if I would bring them my panties. That was weird. I went along with the dirty stories bit, but drew the line at panties.”

A totally decent proposal

“I had a woman hit on me while her husband was away from the table. As she's trying to hand me a piece of paper with her number on it, her husband appears and asks what's going on. She flat out tells him she's trying to take me home. To which he responds with a big grin on his face, 'Oh, awesome, you should come over.' To this day I am still not sure which moment was the most awkward.”

Flickr/scott feldstein

The breast cappuccino ever

“I was running a coffee shop in the early '90s in a nutty-crunchy part of San Diego. We had a regular customer, a young mom, who would bring in a Mason jar with milk in it and ask if we would make a cappuccino for her with her milk. After a while of doing this, the baristas realized it was her own breast milk. They refused to serve her, and asked that I talk to her. I sat down and politely explained that we could no longer make drinks with 'her milk.'.She was puzzled. I explained that many would consider us steaming her breast milk a health violation. She cracked up, it was rice milk. It's still awkward when I run into this person on the street.”

Come at me, bra!

“One time an old woman asked if I was wearing a bra, then full-on grabbed my boob. If it was a dude I would have freaked the fuck out, but since it was an older woman I was lost in emotion. Then she went and had sex in the bathroom and another server walked in on them."

The little guy made a mess

“I was working at a high-end Mexican restaurant and a guest stopped to let me know that a 'little guy made a mess,' and pointed to the floor. The server assumed it was a pile of black beans and the 'little guy' was one of the short Guatemalan bussers. However, after he threw the mess away, the trash can reeked, and he quickly realized that a toddler had pooped everywhere.”

Dan Gentile is a food/drink staff writer at Thrillist. His most awkward restaurant story is better than all of these. Follow him to bold-faced lies: @Dannosphere.