Over-Tipper or Habitual Jipper?

Disclaimer: I tip a lot. I know this, everyone that knows me knows this. My husband and I are also pretty generous when we go out to eat with friends – if we don’t just pick up the tab, we always throw in an extra $5-$8, just in case. That being said, most of our friends are the same way. MOST.


I worked in a restaurant for most of my college career. I worked my butt off, and if it weren’t for the NY tourists that came through and didn’t adjust their tipping scale, I probably would not have made any money. Instead, I was very lucky and made lots of money. It was a valuable experience, because it taught me a lot about courtesy and tipping your servers well.

Now that I don’t have to wait tables to make ends meet, and being more or less able to afford to go out to eat frequently, we tend to take advantage of that and enjoy a meal out a few nights a week. When we go out with friends, 99% of them are just as generous and fair as we are, and we usually leave a pretty decent (20%-22%) tip. If we pick up the tab on a credit card, and our friends give cash, 99% of them never shortchange us – more than likely, they will give us a few dollars too much.

However, we have one friend in particular who either sucks at math, or just doesn’t understand the politics and social norms of splitting a check. Friend rounds to the nearest 5 or 10 (whichever is closer) and “that should cover me, tax and tip.” It never does, and we are always left picking up the rest. I know it’s only a few dollars here and there, never more than $10 at a time.

We went out for Indian food in the city (tapas style), with another couple and Friend, and the bill came to $220 before tip. Friend had to catch the last train out, so $35 out the door, we and the other couple were left to split the remainder. We had a total of 8 drinks – the other couple picked up 4 (for them and us), we paid for one ourselves, and Friend had two. Friend’s contribution was certainly not enough to cover the entire portion of food and drink – let alone tax and tip. Even the other couple mentioned something after Friend had left.

It’s been going on for the past year or so, and I always noticed it, but forgot about it since we are all close and spend lots of time together. But most recently, we went with Friend to a burger place, and we all had a burger and a beer. Friend had the most expensive burger and beer, by $0.50 each. It’s a small amount of money, but when the bill came, it was $58. Plus a $12 tip, $70 should have been split evenly. Friend’s portion of the bill came to just under $18, plus tax and tip. We only had a credit card, so Friend pulled out a $20, which somehow was supposed to cover everything? PJ and I paid $50, while Friend paid $20, when we all had the same things.

I brought this up to PJ, who reacted defensively and basically told me I was being cheap, bitchy, and focusing on negative. And Friend has picked up the tab once or twice, so that’s obviously repaying the favors. But I brought it up to my sister-in-law, because it was honestly bothering me, and she said every group has someone like Friend, and she has noticed this as well, so it’s probably habitual, even if it’s not malicious or intentional. She advised me to either get separate checks, or to just not hang out with Friend as much – which is difficult because we do spend lots of time together.

I think my only option is to always take the check and add it up myself, and just dictate what people owe. I really don’t think there’s any graceful way out of this 😦



One comment

  1. Very good post, on a very good topic. Personally I am a fan of the personal check approach, then nobody can be pissed. When I made a LOT of money I tried to over-tip/over-cover to be able to have a night out with my teacher/waiter friends, but when I lost my job I stopped drinking out, so if you’re at a dinner for 8 and everyone is ordering cocktails and bottles, NO WAY am I gonna pick up my ‘evenly split’ share of the tip. I’ve read some etiquette articles that say that even in this case you should still pay, bc you’re paying for company, but I don’t agree that I should pay $100 for a salad for my friends to spend time with me.

    I do have a beef with over-tippers though, especially the ones that are former waiters. Look, the tip is supposed to be 18% on the price of the meal, not meal and tax. If you’re leaving 18%, you’re not being cheap, you’re paying what you’re supposed to. When you get an awesome steak for $50, you don’t go into the back of the kitchen to give an extra $20 to the chef. You come to the restaurant again. Same with the tip – it’s the price of service. The service is bringing food, not tax. Anyway, my rule of thumb has always been to add my cost of food and drink and add to it 30% – in NYC the tax is almost 9% so this more than covered the total.

    Here’s a thing with an over-tipper: he or she always wants to leave 20-25-30%, on the FULL TOTAL amount (especially in NYC, with big incomes and even bigger egos, well lubed up with the booze). If it’s not a Wall Street banker, it is almost ALWAYS someone who worked in the business (fine), and of those, the majority will bring up that fact as they are leaving the really large tip. And then there is no way for you to not look like a douche. Who hasn’t had a friend, who, throwing an extra $5 on the table looks you in the eyes and says “oh, I know how hard they work, I __ [own waiting experience]___ at ___[swanky place]____ for 2 years.” What’s a good response other than guiltily look away or concede to leaving a few extra? And then you’re STILL that cheapskate person. And for what? For the misplaced guilt for the job that person chose? Because the guy bagging your groceries or pushing shopping card in the rain is working less hard?

    The Big Tipper can go about their big tip agenda in a few different ways. One – take control of the bill, add the tip and then split the check. If you question them on it, in front of the group, you look like a cheapskate. Two – everyone puts in for what they had plus tip and tax. It can still play out diplomatically, if you put your meal on a card, and then – following your conscience of course – add the proper tip. They might still sneak a glance at your amount and double it, and sometimes they like you to see it. If they notice you noticing, the waiter past will come up. I guarantee it. But there is a much worse, way more blatant guilt scenario. Let’s say a bill comes, evenly split between you and your friend. It’s $60 + $5.40 tax. I take my $30 x 1.3 = $39 for food, tip and tax. For 2 people it’s $78, or a $12.60 tip, 21% on the food amount, 19% on the full amount (already over-tipping). But that’s not enough for the Big Tipper. You get either a ‘let’s both leave $40!’, which really isn’t their call, or, if you put down your $39 (maybe I want to give my $1 to a homeless guy!), and they put down their $40, they ALMOST get up from the table, reach into their wallet and discretely-yet-obviously place another $5! “Oh, he was really good! They work so hard! I used to [see above].” It’s supposed to make it seem like it’s just their own little idiosyncrasy, an ode to their past, a recognition of a member of the same tribe, in sociological terms. Oh, don’t mind them. I’m sure that in many cases they don’t MEAN to guilt you, but in many cases they DO, hopefully not for a sense of superiority or for some evil pleasure or misplaced vengeance against a former regular customer who used to be a bad tipper, but to help the waiter even more; but NEWSFLASH: it is still a douche move. Unless you go to all ends your gesture has not been noticed, you just made the regular tipper feel like a slave driver or a robber baron! And the waiter just made $17.60 over an hour and a half, max 2 hours in the burbs. With salary – $24, or $12 an hour (in NYC honestly that’s a 1-hr meal), or 30% more than a bank teller or double the bag grocer. THAT is what you get for taking the ‘hard’ job. And I shouldn’t have to leave the restaurant feeling guilty for not feeling guilty.

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