Ask The Salty Waitress: My Drink Is Hundreds Of Dollars. Must I Tip 20%?

Hey Salty! I like to think of myself as a decent restaurant patron who is polite, not too needy, and tips well. I get really good service at the places I frequent and they seem really happy to see me and my wife.

I turn 50 this month and like scotch. I found a place nearby that has a special 40-year-old VERY rare bottle that's $248 a pour. I plan to get some to reward myself for half a century on this lovely blue rock of ours, and was wondering how much to tip.

If I was getting a special scotch in the $20-$30 a pour range, I'd probably tip $5 for each and a few bucks for a less expensive one. Given the percentages, a 20% tip on my special birthday pour is $50. Since I'm willing to pay $248 for a single drink, the $50 isn't going to cause me any financial harm, but I'm still frugal and think that $50 might be a bit much to tip on fairly low effort (pretty much the same as a $10 scotch, really, and that would be a few bucks tip at most).

This special one-time blow to my wallet will probably be accompanied by dinner, appetizers, a few more drinks, etc. I expect around a $400 tab for my wife and me ($150 food, the rest my ridiculous scotch) which might muddle things if I tip a little less than the 20% or 25% on the full check because over half the tab is a single drink. I don't mind being a little generous, but it's MY birthday, not a random server's day to hit the tip lottery. Or is it?

I'm probably over-analyzing this, but wanted your opinion on how much to tip for my once-in-a-lifetime silly expensive drink.

— Getting Old

Dear Cryptkeeper,

Let me be the first to wish you a happy birthday. You're aging like a fine scotch yourself, I'm sure.

It sounds like you have quite the evening planned with a very specific drink order in mind. (Cheers.) It also sounds like you've thought a lot about how those plans will factor in the tip. In fact, I think you've thought about it all too much. You've thought yourself in circles when there's really only one simple, golden rule to follow: leave a 20% tip. A 20% tip is standard, it's perfectly polite, and for someone like you, who's specifically wondering how to navigate a tipping situation, it's the magic number that will never do you wrong.

To prove it, let's dive into the numbers you're throwing around here (hey, if you can over-analyze, so can I). If you're accustomed to tipping $5 for "a special scotch in the $20-30 a pour range," then what you're saying is you're accustomed to paying roughly a 20% tip. If you tip "a few bucks for a less expensive one," you're adjusting your tip to be roughly 20% of the cost of your order. If your $10 scotch warrants "a few bucks tip at most," then guess what? You're probably leaving a 20% tip, maybe even a little more, on a $10 drink. Ta-da! The golden rule strikes again.

I know, pumpkin, I know: it's a harder percentage to stomach when the sales total starts creeping up. Once the dessert plates are cleared, you and your wife (who I'm hoping has an equally nice birthday celebration planned for herself) stand to owe a tip that could have bought entrees for a family of four. It's not nothing! But consider these the trappings of ordering what sounds like one hell of a special drink.

Here's another reason not to skimp: Servers at many restaurants tip out their bartenders and food runners based on a percentage of sales. Translation: the total dollar amount of the bill is what dictates the percentage passed along to the runner who brought your tray of food and the bartender who poured your drink. You might decide what percentage of tip to leave on the total bill, but the percentage that the server is expected to pass along to these supporting cast members of your dining experience holds steady. So when you skimp on the tip, it hurts your server more than you might think. (And if you're thinking, "Okay then, I'll just order this drink directly from the bartender on a separate tab before dinner," you'll still have this tipping dilemma, because a bartender has to divvy up tips with the bar-back. There's no cheating your way out of the golden rule, honey.)

You've made the decision to go all-out for your birthday, and you've made the calculation that you can afford it. So when it comes to that frugal nature of yours, just find outlets for it everywhere besides your fancy meal. That bill, plus tip, is someone's wages, even if the bulk of its cost was served from a shot glass.

I hope you two lovebirds have a great night. And following the golden rule ensures your server will have one, too.

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