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.

8. History Repeated

I used to work at a very small neighborhood restaurant. Everyone that came in was a regular. Most were couples in their 40’s-50’s out for a quiet dinner, but there was one stand-out.

A VERY handsome man in his early 30’s would come in, it seems, only to break up with women. About twice a month he would come in with a beautiful woman and partway through their meal she would be crying. I always tried to clean the tables near them for as long as possible but I never heard much of his speech.

He always tipped well and was super nice to me and my coworkers, it was just brutal seeing him bring in a new lady and knowing what she was about to go through.

9. Well, that escalated quickly

My shift began at 7pm and when I arrived at the bar at 6, my manager told me there’s a guy who wanted to propose to his girlfriend at this bar and he wanted me to help him with it. I said ‘Sweet, no probs.’ so the manager gave me a ring and told me to put it on top of her drink.

Fast forward to the date, the girl was wearing normal thing you would see at the bar, low cut top, black skirt and heels and stuff. The bar was pretty busy. She ordered a Long Island, so I put the ring on the straw and hand it to him. She had a confused look and then he dropped on his knees. Our manager put on some romantic songs. To my surprise she threw the drink at the poor bloke and ran out of the bar. Later I came to know that it was their second date.

10. For love

I used to wait tables at a Bob Evans that was located across the street from a nursing home. Whoever chose that location was a genius because old people love Bob Evans. I had an elderly couple who came in every day for lunch and ordered the same thing. It got to the point that they I would have their meal on the table by the time I saw them crossing the street from the window. (They usually only got applesauce/banana bread/mashed potatoes.) One day the old man came in alone after a week of absence. He never said it, but I knew she had died. He still ordered for her, and let the food sit on her side of the table. Every. Day. I cried more than one time delivering it. I hope one day my future husband loves me that much.

11. Should have gone for smoothies

I work in an Italian restaurant. A few years ago I waited on a guy and girl who met for the first time upon arriving at the restaurant. There were awkward pleasantries exchanged at the door and then they were seated.

When I was taking their order the guy asked if we had soup because he had mouth surgery a few days prior and chewing food was still a little rough. We don’t have soup, so I explained that the “softest” food on the menu was gnocchi. He ordered the house gnocchi and proceeded to cut each tiny dumpling into four or more pieces and slowly chew each piece. He ate that entire dish over a 3 hour period and the girl stuck it out for the whole thing. She looked miserable and I’m pretty sure they never saw each other again.

12. Double Dipping

I had a regular sitting at my bar in a chain restaurant about two weeks ago. He sits there for an hour, leaves for 20 minutes or so, then comes back complaining that he’d been stood up. The date was supposed to have arrived an hour before he mentioned anything. Poor guy.

All of a sudden this woman appears, apparently his date. Nothing out of the ordinary except for the fact that she was an hour late, so I continue making drinks for the restaurant.

Couple of minutes later and a waitress comes up asking if the woman was on a date with the guy at the bar. I respond yes and ask how she knew. She told me that the woman had just left her (the waitresses’) section and had been on a date with another man.

13. T.M.I.

I’m a bartender at a major chain restaurant. A couple stumbles in about 15 minutes before close. They’re talking loudly and sit at the bar. I’m a little pissed off so I finish wiping down the bottles before acknowledging them. I can hear everything they’re saying but it’s all very coded language so I have no clue what they’re fighting about.

“You promised me three times!” “I can’t I can’t, I just can’t do it,” the woman says.

When I turn around and ask them what they would like to drink the man orders 10 shots of the strongest liqueur we have (which is Rumplemintz). I tell him I can’t serve that many shots to just two people.

He says, “There’s three of us. I’m trying to make it two people,” and pulls out a $100.00 bill and lays it on the bar.

14. Other options

Served a couple a few months ago. Everytime I walked over, he would always be the one talking, and she would just be sitting there not having a good time. At the end I asked if it was one bill or separate and she immediately piped up “SEPERATE”. I go and take his payment, and as I hand over the Debit machine to the girl, I see the guy take his phone out and start swiping through tinder.

15. “douchenozzle”

I was waiting on a couple once, had to be a first date. The guy was constantly rude to me, and the girl was very apologetic. He asked for a well done filet mignon, when I started to advise him that it would be burnt as such and to ask if he’d like it butterflied, he he flipped his lid yelling “you don’t tell me how I like my steak!”

She got up, pulled out a $20, handed it to me, and walked out without a word. He shouted after her to come back, didn’t even get up til she was out the front door though. What a douchenozzle.

16. Hot stuff baby

I worked in a restaurant that had a huge selection (150+) of hot sauces. We sold them by the bottle but customers could sample any of them and use them on their food. A couple came in, the guy started bragging about how much he loved hot sauce and how he never found one that was too hot. He asked for the hottest one we have. I brought the bottle to his table, he filled a spoon with the sauce and made a big production of how he was going to eat it. I told him not to, the hostess told him not to, the waitress serving the next table told him not to… he put it in his mouth, started choking and gagging, puked on the table then passed out and did a faceplant right into the puke!! We called 911. He woke up right away and kept gagging for a while. He refused treatment when the paramedics showed up. They left without even ordering a meal! The girl told one of the restaurant staff that it was their first date.

17. Vanishing act

Late to the party here but I was bartending in NY and watched this couple that had met on Tinder have their first date sitting at my bar. The girl was a complete weirdo. Kept bringing up the fact that the dude she was with could be a psychopath and could murdwr her (he had given no indication of this) and went on tinder while he was still sitting beside her at the bar. Kept telling him he was lucky that she agreed to meet him at all and she didn’t think he’d be this boring. She ordered about 5 or 6 LITs and several shots, he literally just had 2 beers. She made him pay for everything. My favourite part of this was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. Straight up thought he had disapparated out of the bar.

18. Hope it wasn’t the second date

This lady came in for lunch and let me know she was waiting for someone. When her lunch date got there I took his drink order, grabbed his coke and brought it to the table. As I’m placing it down I see a positive pregnancy test in a Ziploc on the table in front of the dude. Her excited face, his shocked, semi-disgusted but trying to look happy face, my WTF face. Awkward level went up 100%. I murmured something about congratulations and left the table as fast as I could.

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