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.