A generous friend regularly offers to pick up the check when we're out together. I'm grateful, but I'd also be happy to pay my share. How appropriate it is to fight over the check? And how can I know if he really wants to treat?

In plenty of cultures, friends take turns grabbing the check, or assume that whoever issued the invitation pays the bill. Would that American tradition were so simple. Instead, we improvise — every time. There's the "divide everything equally" school. There's the "pay for what you ate" approach. And then there are situations where one person — a wealthy friend, a date, or your dad — simply insists on paying for the whole thing.

Let's assume your friend isn't trying to seduce you. (He's not, right? Because that's a whole other column.) Why else might he be so generous? If he's a hot-shot executive and you're a teacher, or if his last name is Bloomberg or Trump, he may simply feel that he has money to spare and enjoy sharing it. In that case, you should sincerely try to pay your share (never assume he's paying), but if he's still insisting after a couple of vigorous attempts, you can accept with thanks. Then treat him no differently than you would any of your other broke-ass friends.

On the other hand, maybe you're in more or less the same boat financially. If he's that kind of generous-to-a-fault person who would spend his last dime on your dinner, or if, say, he's lonely and you feel like he's trying to buy some company, fight harder for the check. (Not literally; avoid arm-wrestling in the bistro.) Let him get this one, but next time, tell him firmly that it's your turn, and your pleasure.

Last week in the Awkward Dollar: how to handle guilt-tripping, dolphin-loving, fund-raising family members.

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