For many servers, Valentine's Day is considered the worst working day of the year -- even worse than the controversial "Kick Your Server Day." This is due, in large part, to the fact that restaurants are flooded with people who typically don't go out to eat, couples on the brink of breaking up, and couples who are needlessly demanding about their prix fixe meals. We talked to some of our favorite servers around town and they told us their most memorable tales from the times Cupid's arrow didn't quite hit its mark.
A few years ago, a couple came into the restaurant toward the later side of the evening. The woman ordered an appetizer, a steak, dessert, a couple of cocktails -- the whole nine yards. The man had nothing. Water, that was it. I don't even remember him taking a bite of her food.
When they were finished I brought the check. He gave me his card and I went to swipe it. Declined. I tried once more although I knew the computer was never wrong. I brought the check back and he was totally laid-back about it. I left the table so he could switch out his payment.
He started explaining that it was his only card and he didn't have any other way to pay for the meal. Then he asked me if I could cover him.
A minute later I was at the computer ringing up someone else, and he came up behind me looking incredibly distraught. He started explaining that it was his only card and he didn't have any other way to pay for the meal. Then he asked me if I could cover him. I looked at him sideways and asked him exactly what that meant.
He said, "You know. Help me out?"
"You mean pay your bill?" I replied.
He said, "Yeah. I mean, yeah, I guess. Or... like... maybe like take some stuff off or something...?"
After I assured him there was absolutely no way I was paying his tab for him, he went back to the table and I awaited the inevitable dine and dash. To his credit, he walked back up a few minutes later with his date's card and was very apologetic.
It's probably the only time a stranger has asked me to give them $100, and definitely the only time someone has asked me to straight-up pay their tab.
I don't think the woman left happy.
A guy proposed on the patio of the Pizza Cafe and the girl dropped the ring through the deck slats. This was before the overhaul of the patio, so it was basically an animal kingdom down there. Half the kitchen staff went underneath there looking for the ring and we finally found it. The guy was just sweating bullets and freaking out and was so thankful.
Then he tipped me $2 on $40.
A woman called the Peabody two months in advance to set up an extra-special date. The woman had given staff handwritten instructions, put rose petals on the table, and rented a room -- the works. When it was go time, the guy just thought they were having dinner, not a date. I walked over to present Champagne and the guy, now clued in, told her she was crazy if she thought he would ever date her. Then he left and she proceeded to chug that whole bottle of Champagne. It was so painful to watch. Luckily, she hooked up with some random guy at the lobby bar, so I guess it wasn't an entirely wasted evening.
I had a guy propose on the patio at Hunt Phelan. He had Champagne, chocolate-covered strawberries, a reservation for our six-course dinner with wine pairings, and the Masters Suite booked for the night. He and his girlfriend had checked into the room several hours before. They came downstairs and had a long, leisurely dinner. He got down on one knee during dessert. She obviously had no idea that he was going to propose.
She stood up and said, 'I can't marry you and I can't do this anymore,' in that tone of voice usually associated with minor government officials dealing with the public.
She kept repeating, "Oh my God," in a strange falsetto. She stood up and said, "I can't marry you and I can't do this anymore," in that tone of voice usually associated with minor government officials dealing with the public. Then she turned on her heel and briskly walked away. It took the poor guy a full two minutes to compose himself enough to follow her upstairs. He was back in less than five minutes. He said she wasn't in the room and asked me if I had seen her. I had to tell him that I saw her get in her car and drive away. He was completely thunderstruck -- just hung his head and went back to his room.
He had spent a ton of money and the ring had to cost $10k. At the moment, it was Fellini-like.
Two years ago, I had two couples sitting next to each other at my bar on Valentine's Day. One of the couples was in their mid-30s and the other in their mid-to-late 50s. The 30-somethings seemed extremely nice, but very awkward at the start of their meal -- like they couldn't get quite comfortable. I assumed it was just the stigma of the holiday and maybe the pressure of spending it at a higher-tier kind of restaurant, so I took extra time to get on a personal level with them.
After a couple of hours trading stories back and forth about Valentine's Days gone awry, they were completely relaxed and seemed to be having a genuinely good time. After they paid, the husband went to the restroom and I asked the wife if they had any special plans for after they left dinner. She blushed a little and told me it was their five-year anniversary that year, and they had decided to go a little "out of the box" to make it really special.
Since I had such a great time getting to know them over their dinner, I wasn't shy about asking what it was that they had planned. At this point, she blushed furiously and said they were finally doing something they had always talked about but never had the fortitude to go through with… and then she asked me if they could buy me a drink after I got off that night.
The entire time this was going on, the 50-somethings, who were both very inebriated after finishing their meal in the dining room, were in the middle of a knock-down-drag-out marital fight that included accusations of adultery and a proposal of divorce. They passed every stop of the train from the wife sobbing, to the husband admitting to an affair, to the wife trying to hit him with her purse. Luckily, this story has a happy ending: They made up with crying and kisses (quite a long time after we closed) and told me they were making their way to Paula Raiford's to dance.
I still wonder whether that young couple ever found someone to complete their ménage à trois fantasy and just how much cocaine it actually took to fix that broken marriage.
Last year, this guy brought a woman of the night, if you will, into Strano. She got frustrated trying to comprehend the prix fixe menu and yelled at me and her date. Then after she was completely gone on Long Island iced teas, she asked him (loud enough for my other tables to hear), "What hotel are we going to fuck in?" Needless to say, it was awkward.
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