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Dear Sugar
Whenever I go out with a group of friends, one of the gals in our crew never contributes to the bill. She always keeps her hands in her pocket or she pretends to be searching around in her handbag for her wallet until all of the cash has been collected.

We know that she makes a great living, so it's really awkward that she never offers to pick up so much as a round of drinks...ever This behavior is getting old quickly and I think it's time to confront her, but it's always so funny when you're talking about money. Do you have any ideas on how to approach this? Chagrined Cheryl

Dear Chagrined Cheryl
Keep your distance from the check the next time you are out. See what happens when the time flies by and the bill just sits there. After a fair amount of time if she still says nothing or doesn't pull out her pocketbook say something like this:

"Ok, girls, let's settle up this check. Everyone owes "X" amount and that also includes the tip. If you (point to your friend) don't have cash on you and you want to pay with a credit card, that's ok."

This will put her on the spot and once everyone's shares are all out and paid, she'll have no choice but to dig into her wallet. If you are feeling frustrated, you could even ask her to cover your portion since you payed for her drinks the past several times you've been out. It's a little passive aggressive, but at least it's out there.

She will probably get embarrassed. She may even get angry, but that's the price to pay for being cheap. After all, nothing ever comes for free! If she claims that she doesn't know what you are talking about then just call her out on it. At least now you've brought the issue to the table.

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