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[Image: Robyn Lee]

Dear Molly,

One of the nicest parts of adulthood is being able to enjoy a nice dinner out with friends without utter chaos as soon as the bill arrives. During most dinners, my friends and I are able to pay quickly and appropriately, without any fuss over leaving an inadequate tip. However, one of my acquaintances takes it upon himself to ensure everyone has tipped well enough, going above and beyond to ensure everyone is leaving what he deems to be a proper amount. At best, this involves loud exclamations of 'I tipped $15! What did you tip?' At worst, it involves actually telling a bartender or waiter "I tipped you an extra $2,' which just seems incredibly uncouth to me.

On the other end of the spectrum, I've dined with people who have not only not tipped, but have barely contributed enough to cover their own entree, relying on others to pick up the tab. Unabashedly, at that. Obviously, neither situation is ideal. So, my question is: How do you ensure your party tips well, without seeming like an overzealous jerk about it? Are there any polite ways to prompt the inevitable post-dinner conversation?

Sincerely,
Just the Tip

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[Photograph: Tip Jar from Shuttershock]

Dear Just the Tip,

If only it were just the tip.... This isn't about just the tip, it's the whole thing.

I get more questions that are essentially some version of "how do a group of adults split a bill"? than any other question. (Please see How to Split a Check for a past example.) And while I honestly understand that there are some real cheapskates out there, what I don't understand is why other people keep going to group bill-splitting dinners with them.

It sounds like most of the time you're faring okay. You know the pleasure of everyone simply, quietly, and maturely paying their fair share. Delightful!

How to answer the guy who asks how much you tipped? I'd be tempted to just tell him. The poor thing seems obsessed. Or in need of an ego boost that he seems to get through tipping more than other people, which is excellent luck for the server in question. Telling the waiter how much extra he tipped strikes me as pathetic, but it reflects on him, not you, so I would ignore it.

In terms of the people not kicking in enough, a direct approach is best. "Hey, it looks like you put in $25, but that doesn't cover your share of the tax and tip," is a great place to start. It states facts rather than makes accusations and gives the cheap-o a chance to pretend it was all an accident or miscalculation. I don't think you should need to do that more than once. Twice if they're ballsy.

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About the Author: Molly Watson honed her ability to guide others in tricky situations by telling her little brother the best way to do everything. See what she has to say beyond dining at Ask a (Sensible) Midwesterner. Catch her work as a recipe wizard at Local Foods.

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