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Even though it's 2008, many people are still programmed to avoid discussing money at all costs, says Leonard Schwarz, who co-authored the new bookIsn't it Their Turn to Pick up the Check? with Jeanne Fleming. Here is some advice for handling those awkward money moments with a little bit of grace:

An unpaid loan.Many of these casual loans between friends or family members turn into gifts because they're just never repaid. Before you agree to write a check, weigh all of the circumstances involved. How will the money be spent? What do you know about this person's spending habits? What are his alternatives if you say no?

Get the amount of the loan in writing, along with a schedule of repayment. (These days, there are even companies like Virgin Money that can help you do that.) If you're close enough with someone to lend him money, you should feel comfortable hashing out the specifics. But if that's really not your style, or you're in a position to forgive the loan if need be, you should probably just come to terms with that as a possible outcome, Fleming says.

An uneven check. We've all seen it happen: Someone who doesn't drink gets stuck splitting the bill, and the cost of two bottles of wine, with the rest of the table. If you're caught in this situation, Schwarz and Fleming say you need to speak up, but how do you go about it without spoiling the mood?

"The best way to ensure that a check is split fairly is simply to propose that it's split fairly," Schwarz says. That may mean reaching for the check as soon as it hits the table and tallying up what everyone owes, or you might try to address the issue beforehand. You can ask the waiter to bring separate checks or you can talk to your friends and suggest that since you don't drink, it would be great if they could pick up the tip if you split the bill to even things up a bit. Chances are your friends aren't trying to stiff you; they just see an even split as the easiest way to handle the bill.

A generous gift. What do you do when a friend shows up at your birthday party with an iPod and you know you can't afford to match it when her big day rolls around next month? Nothing, says Fleming, except send a thank-you note. Just because you're given something that is overly generous doesn't mean you have to respond in the same way, especially if you're not financially comfortable doing so.

"Remember that this person gave you a particular gift because they wanted to, not to show you how much money they have. Just give them something that takes a lot of time or thought in return," says Caroline Tiger, an etiquette expert and author of How to Behave: A Guide to Modern Manners for the Socially Challenged.

A nosy friend (or neighbor). If your co-worker practically asks to see a receipt every time you show up with a new outfit or pair of shoes, there's no reason you have to buy into it. If a question feels too personal, just opt out. There are a million ways to do it, but merely saying "It cost enough" or "I'd rather not say" are probably the easiest. After a while, she'll stop asking.

A wealthy friend. Checkbook balances vary among friends as frequently as hair color or dress size, so there's a good chance you've found yourself invited to a dinner or event that you just can't afford. "If it's really out of your price range, suggest meeting for lunch instead," Tiger says.