Answer: That's just the way the investment cookie crumbles, is it? Drew's probably also thinking that if his company had been the next Google, he'd be a hero for making Mandy rich.

Well, he's right that a good outcome can obscure bad judgment. But he's wrong to imagine that what happened to Mandy's inheritance is nobody's fault. It's his fault. Moreover, your brother wasn't just foolish or unlucky, he was unethical. First, instead of handling your niece's money responsibly, he poured all of it into a single, untried business. If Drew either didn't know enough or didn't care enough to invest more wisely than that, he had an obligation to turn the job over to someone who did.

Worse, not only was Drew irresponsible, he engaged in self-dealing. That wasn't just any business he put Mandy's money in, it was his business. What could be a clearer conflict of interest?

If we had your brother's photo to hang on our Money & Ethics Wall of Shame, we'd be putting it at least as close to Bernie Madoff's as to Scrooge McDuck's. The guy is unequivocally obligated to make Mandy whole. Pronto.

Questions? Email Money Magazine's ethicists – authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press) – at FlemingandSchwarz@right-thing.net.

A: Like Humphrey Bogart in Casablanca, you've been misinformed. Individuals are not legally liable for debts their spouses incurred before they were married. As a practical matter, though, those bills do indeed come with your fiancé. The fact that you're not personally on the hook doesn't mean that, as a couple, you won't have to figure out how you're going to pay them off.

We understand why you're reluctant to put yourself in this kind of hole. But before his heart attack, Alan was the man you were committed to spending the rest of your life with, and now he really needs you. Are you obligated to marry him? No. But you do have a big-time moral obligation to help the guy out.
Questions? Email Money Magazine's ethicists – authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press) – at FlemingandSchwarz@right-thing.net.

Answer: In a word, No. And in two words, Absolutely Not.

Lending a flakey friend that kind of dough is a very generous thing to do, and insisting on some security in no way dilutes your generosity. After all, nowhere is it written that, in lending people money, you are required to make it as easy as possible for them not to repay you. And neither is it written that at the Bank of Friends and Family, the borrower gets to set the terms. If Tom is unhappy with the arrangement you propose, he can always try to find a friend or relative —- or, of course, a real bank —- who'll offer him a better deal.

That said, we suggest you not secure the loan with his car. Why? Because if Tom's as irresponsible as you say, there's a good chance you'll end up having to choose between two equally unattractive alternatives: taking possession of your buddy's car (and there goes your friendship) or ending up with nothing.

Instead, consider asking Tom to give you some collateral to hold until he repays you: a fine watch, say, or his prized Stratocaster -— something of sufficient value to give him a real incentive to pay off the loan. Because you're right: You don't want to bet $2,500 on the good intentions of an irresponsible friend.

Questions? Email Money Magazine's ethicists – authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press) – at FlemingandSchwarz@right-thing.net.

A: Maybe. The key question: Is your dad's lady friend in the dark as to his resources or is she just uncaring? If your father has been pretending to be her financial peer, you can't blame the woman he's squiring around for his extravagance. If not, though, she -- like every adult -- has an obligation not to allow someone to spend more money on her than the person can afford.

But unless the merry widow has been holding a gun to his head, it's your dad who's responsible for jeopardizing his financial security. While he has a right to spend his money as he chooses, he also has an obligation to see that he doesn't run out of dough and leave others - you, for one, us taxpayers, for another - stuck with his support.

Questions? Email Money Magazine's ethicists – authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press) – at FlemingandSchwarz@right-thing.net.

Answer: Call us unsentimental, but gift-giving is a transaction as well as a pleasure. And, usually, part of the deal is that the presents don't just go one way. Reciprocation of some type isn't only gracious, it's required. So had your friend, say, accidentally left a gift intended for you behind on a train or ordered something for you that never arrived, she'd still owe you one. Bad luck and good intentions don't wash away obligation.

But your situation is different. Your friend gave you a gift that you chose to reject. While it's nice to get something you want or need –- and these days we've all gotten used to the failsafe gift (a gift card, for example, or exchangeable merchandise or an item from a "wish list") –- the fact is that givers have no obligation to give a gift that is certain to please, only to give one that they hope will please.

Obviously, Gretchen struck out on her selection of a gift for you. But she unequivocally reciprocated your gift to her, and that's all she needed to do. It doesn't matter that she got her money back, because what she gave you was a present, not an I.O.U. Would it have been thoughtful of Gretchen to replace the subscription with a different one? Absolutely. But as long as she made a note to never send you that magazine again, she hasn't done anything wrong.

Questions? Email Money Magazine's ethicists – authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press) – at FlemingandSchwarz@right-thing.net.

Answer: Apparently Adam doesn't take rejection well.

We hope you've talked to a lawyer and the police about whether you have grounds for bringing a civil complaint or pressing harassment charges against your former squeeze.

But don't put your check book away just yet. After all, two wrongs don't make a right: The fact that Adam's behaved badly doesn't cancel out your obligation to repay him. Even if you have a strong claim against him for money damages related to his contact with your business prospects, it's not okay to declare yourself the winner of a lawsuit you haven't filed and award yourself $12,000.

Plus, Adam wasn't wrong to expect you to pay him back promptly once you split up. True, when he lent you the money, he didn't set a repayment date. But in accepting his generous terms -– an unsecured personal loan with no repayment date and, probably, no interest –- you were also accepting the obligation to honor the spirit in which the loan was offered, namely, that it was a sweetheart deal (in this case, literally). Girlfriends don't have to rush to pay back open-ended loans like this. But ex-girlfriends -– especially ex-girlfriends who dumped the lender –- do.

Answer: Very irritating, these folks with an ax to grind who relentlessly forward "interesting" e-mails to everyone they know.

Of course you can ask Karen to stop with the clipping service. But there's another issue here. We presume that her financial advice is informed by her assessment of the government's economic policies. That doesn't necessarily mean she's steering you to investments that are wrong for you. But you might ask Karen how her philosophy shapes her recommendations. After you hear what she has to say, you need to make a decision. You can skip the e-mail, but you can't duck the question: Do you want your investments managed by someone whose take on the economy is the opposite of yours?
Questions? Email Money Magazine's ethicists – authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press) – at FlemingandSchwarz@right-thing.net.

Answer: Hold on. Before you divvy the bills, there's a lot more to consider than bank accounts and kids. What if, for example, one sister is providing most of your parents' day-to-day care? Or one of you previously received large gifts of money from your parents? Or the only reason one of you can't contribute is that she's a spendthrift? To equitably apportion your folks' expenses, you need to put everything on the table.

Not a discussion you want to have? We sympathize, but have it anyway. While the three of you needn't do exactly the same things for your parents, you have an ethical obligation to one another to share fairly -- truly fairly -- the responsibility for looking after them. That's unlikely to happen without, as the diplomats say, a full and frank discussion of all the issues -- and, we suspect, a little friendly persuasion.

Questions? Email Money Magazine's ethicists – authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press) – at FlemingandSchwarz@right-thing.net.

Answer:  But what if you take longer showers?

We're not kidding. There are countless ways you and your ex consume water and energy unequally. Perhaps one of you likes to crank up the air conditioning or to grow tomatoes or to stay up late microwaving popcorn and watching movies. You can't pick just one variable in the utility bill equation and then cry foul.

Moreover, life is filled with per person, as opposed to per usage, fees. Planes, trains and buses, for example, charge per seat, not per pound, even though heavyweights cost more to transport than bantams. Rare is the car wash that has more than two price points, even though autos come in all shapes and sizes. And, as you'll discover once you sell the house and start looking for new digs, rarer still are roommates who are willing to split the utility bill on anything other than a per person basis.

Questions? Email Money Magazine's ethicists – authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press) – at FlemingandSchwarz@right-thing.net.

Don't bartenders put up with enough as perennial straight men without catching flak for pouring the occasional free drink? Seriously, a happy customer is a return customer. And while Jake may not know it, the hospitality industry has a long tradition of offering perks to regulars and big spenders -- a cocktail here, a room upgrade there -- to keep them coming back.

So if Jake's getting those complimentary drinks because his fanny's frequently on a bar stool, there's no problem. And there's no problem either with bartenders accepting Jake's fat tips, whatever his motives may be.

But is there a dark side to this practice? Absolutely. It's if, in exchange for Jake's largess, bartenders are serving him more free drinks than the bar owners -- the folks who are actually paying for the alcohol -- would approve of. In that case, you're right: the bartenders are stealing and so is your pal. And what Jake's leaving isn't a tip, it's a bribe.

Questions? Email Money Magazine's ethicists – authors of "Isn't It Their Turn to Pick Up the Check?" (Free Press) – at FlemingandSchwarz@right-thing.net.