18 First Date Stories…From the Waiter’s Perspective

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Dating is hard. Like really hard. And an awkward first date can feel utterly miserable. We may think we are the only ones who have experienced that horrendous first date, but don’t be fooled. Here are 18 stories from AskReddit users to assure you, there are others who see and feel all the awkward right along with you.

1. Speak for me

Couple sits down at my table. Do the usual greeting. Ask them if they would like to start out with a beverage. The female replies, “Coke, please”. The male stops her, interrupting “Uh, make that a diet coke. I’ll take a jack and coke”. The date didn’t get any better.

2. Big Fan

We had an older lady come in on a Saturday morning. She happily informed the server that she was waiting for a date, and ordered a mimosa to drink. About three mimosas and forty-five minutes later, we start to think maybe her date is a no show. The waitress sits down and starts talking with the lady, trying to assess the situation, see if she still wants to order and what not.

That’s when it gets strange. The lady says that her date was going to pay for the meal so she didn’t have any money, and she wanted a fourth mimosa. Meanwhile she’s cheerily looking out the window for her date, obviously nervous / excited to meet him, and very talkative. The server asks the manager what to do, so he sits down at the booth with the lady to talk with her. Turns out, her date was Lynyrd Skynyrd and she had dementia.

3. Mother knows best

A couple came into the chain restaurant I worked at. Both looked like they were mid 30s. I go to take the order and the guy says “Hold on, let me call my mom. She can tell me what I would like better.” The lady just looked at him like “I messed up… I messed up badly.”

4. Real life movie

A couple on a date, sitting having a meal and chatting, just a normal date. A guy comes in who turns out to be the woman’s soon-to-be ex-husband and, at first, just asks to talk to her. She refuses. He asks louder and she refuses louder. Lather, rinse, repeat, getting louder. The man on the date stands up and tries to calm the ex-husband down. He starts screeching at him and her and everyone around. The ex-husband sweeps all the food and drinks off the table on to the floor and wants to fight the male date. A nearby waiter steps forward to try to calm the ex-husband down. He takes a swing at the waiter. GAME ON! All the other waiters surround the guy, drag him to the ground and drag him out of the restaurant. Ex-husband is screaming profanities as he’s being dragged out, woman on date is sitting in silence.

All is calm after the ex-husband is dragged out. After a few seconds of stunned silence the woman on the date smiles nicely to her date and says, “So… Do you like movies? Have you seen any good ones lately?”

5. Concerned Patron

I was working in a small restaurant with two floors. A woman and a man came in and I had a table for them upstairs. It looked like they had a first date because they were asking those “getting to know each other”-questions. After ordering food the woman had to go to the toilet, which is downstairs. As she walked to the stairs, the food arrived. She walked down, tripped and fell all the way down knocking her head on the ground. Two colleagues immediately rushed over to her to see how she was doing. She was unconscious and bleeding from her head so they called an ambulance. I went to the man while he already started eating and told him his partner (didn’t know how to call her) fell down the stairs and that she was unconscious and that an ambulance was on the way. He walked to the stairs, looked down and walked back to his table to finish his food. Later the ambulance arrived and I asked him if he wanted to go with her to the hospital and he said no while finishing her food as well. It was so awkward he just sat there for another 45 minutes eating, drinking, paid the bill and left. I still don’t know what kind of relationship they had and whether the woman is okay.

6. Repeat Offender

The favorite date I ever got to see was a super hot woman and a pretty good looking guy. They ordered tons of drinks, several apps, two steak dinners and a lobster, then dessert. At this point the guy excuses himself to go to the bathroom. The dessert shows up and the girl waits for him to comeback from the bathroom. 10 minutes go by and she asks one of the busboys to check the restroom. The guy had bailed on her and left the check for her. All of that was about $150. She started crying, it was awful. Most of the waitstaff tossed in to cover the bill and one of the waitresses gave her a ride home. The guy was banned from the place and we got to toss him out 2 times trying to come back with other dates.

7. Awkward Conversation

I used to wait on this guy and a woman who would come in and sit in the bar area every now and then. A great couple, always very sweet to each other like they were newly in love. They always ordered the same drinks, split an app and tipped very well. One day I saw him in the restaurant on a very busy Friday night and I immediately start in with a friendly, “HEY!” and see that he’s not eagerly smiling back. He’s in the booth with a woman that I’ve never seen before who is looking over the menu leisurely, sitting across from 2 energetic kids asking their dad if they can have chocolate milk. It was beyond awkward. I have no idea why he’d bring his family to he and his mistress’s favorite restaurant, but I didn’t feel comfortable waiting on them and transferred the table.