I worked at this restaurant in high school. It was basically a diner, albeit a really good one. Maybe it was a little nicer than a diner. It definitely wasn’t fancy. Not too fancy anyway. One of the cooks was named Francisco, and everyone called him Fancy-Pants Francisco. But that’s about as fancy as it got. And they made homemade gelato, which was pretty cool. And yeah, maybe a little fancy, but mostly due to the fact that gelato is just a fancier, more Italian way of saying ice cream. Italians are pretty fancy in general. In a good way, obviously.

Anyway, every once in a while this guy would come in that everyone in the restaurant called “Big Tipper.” It’s not the most creative name, but it was spot-on and it wasn’t at all an exaggeration. This guy would walk in with his family, all of them draped in their velvet Sunday sweats, and the rainmaking would commence before they even got to their table. We had a bunch of hostesses, a few middle school girls who stood at the front and handed out menus. Their jobs were basically pointless, because most people who dined at this restaurant, if given a table, immediately demanded a different one, probably just to make sure that they could visibly boss around as many employees as possible during a single meal. Big Tipper would get a table a hand each of the hostesses a fifty dollar bill.

That’s huge. That’s like exactly what they would have made after a whole night’s work. Fifty bucks each and this guy hasn’t even sat down yet. Maybe you’re beginning to understand why people got excited about this guy. I would never get to take Big Tipper’s table – he wasn’t throwing around all of that money to impress sixteen-year-old-Rob – but that was fine, because the wait staff pooled all of the tips at the end of the night anyway. So I probably had it the best. There was no work on my part, no chance of screwing up the big tip, and I still got to cash in all of my extra big-tip money for singles at the end of the night and shower myself in dollar bills just like everyone else.

This restaurant is one of the cheapest restaurants anywhere. You could bring in your whole family, get dinner and dessert, and it would still be hard to spend a hundred bucks. When most of the customers are leaving maybe two bucks on the table after a meal, having the Big Tipper come in was like winning a small lottery. He and his family ate, they left multiple hundred dollar tips, and left, handshakes and kisses to all the staff on the way out. It was great.

I never really interacted with Big Tipper personally; I was always benefiting from the periphery of Big Tipper’s generosity. But when I think about him now, and when I thought about him back then, I always loved and hated him equally at the same time. It’s hard to explain. Or maybe it’s not. I loved him because he was just this presence, this giant dollar sign that came in and made my life a little richer, with nothing asked on my part. Maybe he didn’t even know that we pooled tips. But it was just nice to have somebody walk in out of nowhere and give me a lot of extra money.

But if I weren’t a part of that extra money, I would have totally hated Big Tipper. Who the hell does this guy think he is? Everything about it seems so calculated. He picks the most inexpensive restaurant around, I think, on purpose, solely for the fact of inflating the appearance of his tips. If he went to a steakhouse or to any other nice place and ordered the way he and his family ordered, a hundred dollar tip, while I’m sure it would still be welcome, probably wouldn’t have seemed like that big of a game changer. You’re getting into percentages here, like a fifty percent tip versus a two hundred percent tip. The tip itself is the same, so just deflate the cost of the meal to bump up the perceived percentage of generosity.

Which leads me to believe that this guy, this Big Tipper, doesn’t even care about the food that he’s eating. All he cares about is walking into a restaurant, opening the door for his wife and kids, looking out amongst the tables and seeing every employee turn to him and smile. Is this guy’s life so empty, so devoid of meaning that he’s willing to shower a complete group of strangers in absurd amounts of cash just to have a shadow of the feeling that he’s well-liked? And, since I clearly believe this to be the case, he’s OK with all of this? He looks out at the world and says, I’ll just buy whatever I want in my life, cars, houses, other people’s affection, all of it, all of it’s for sale.

I’m still waiting tables, and every time somebody gives me a big tip, like bigger than I deserve, I’m always a little apprehensive. What do I do now? Am I supposed to give a really extra big thank you? Am I supposed to shake his hand? Kiss his ring? Get down on my knee? Twenty percent is totally appropriate. That’s fine. Money for a job well done. Twenty-five percent, OK, I get it, you like being generous. That’s great. Thank you very much. See you next time. Hope you had a nice evening. But thirty percent? Am I really that good of a waiter? I don’t think so. Thirty-five percent? Excuse me sir, but I don’t think you added up your bill right. Anything forty and over and I’m hiding out in the basement until that table is out of the building. No thank you. No goodbye. Just get the hell out, because I don’t know what you’re expecting from such a big tip, and I’m not at all ready to reciprocate.