Question: Is there anything wrong with asking a good friend to secure the loan I'm giving him with the title to his car? Tom really needs the money, but he can be pretty irresponsible, and I don't want my $2,500 to become a gift.

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.

Question: A friend gave me a subscription to a magazine I don’t care for. When I canceled after one issue, the magazine sent the refund to Gretchen. I don’t want to seem small, but especially since I’d given her a nice present, shouldn’t Gretchen have given that money –- or another gift –- to me?

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.
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Question: We often eat out with another couple, always dividing the check 50/50. Since Pam and I are economizing these days, we no longer order drinks in restaurants. Our friends do, though, and they don’t seem to notice that splitting the check has become an awfully good deal for them. I think they should offer to pay for their booze, but Pam thinks our long-standing 50/50 arrangement is fine. Who’s right?

Answer: No wonder your friends aren’t cutting back on the cocktails in order to economize. They’ve got you to pick up half their bar tab. Count your blessings they’re not drinking more, now that their libations come with a 50% discount.

While we sympathize with Pam’s desire to avoid unsettling the friendship, this boat needs rocking. Presumably you’ve been splitting checks with your friends, not only because it’s gracious and easy, but because over time things have more or less been evening out. But unless the stimulus package includes some cocktail tokens for you, that’s no longer true — which means it’s time to change the deal.

Our advice? Stop wishing your friends would offer to pay for their drinks and tell them nicely but directly that, since you’re no longer ordering alcohol in restaurants, you’d like them to ask for a separate bar tab. Of course, you might want to first fortify yourselves with a stiff one at home.

Cheers — and good luck.

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.

by JEANNE FLEMING, PH.D. and LEONARD SCHWARZ

Question: A good friend is investing $25,000 in an alternative-energy deal that looks very promising. He says he can arrange for me to get into it, but in exchange he wants 10% of whatever profit I make. I think he's being incredibly greedy, but he says that he deserves to be compensated for opening an otherwise closed door. Does he?

Answer: If the dealmaker's name is Madoff, run. And even if it's not, remember: While alternative-energy projects have a certain cachet these days, so did hedge funds and Las Vegas real estate not that long ago. In short, caveat investor.

Should you still decide you want in, however, it's not unethical in the business world to compensate someone for opening an otherwise closed door (bribes are another story). But to flip Michael Corleone's famous phrase, this isn't business, this is personal. And in the personal arena, friends don't charge their friends fees. Unless your pal is a professional financial adviser – that is, someone who earns his living finding and vetting investments – what he deserves for a favor like this is your sincere thanks and a nice bottle of wine. If the deal turns into a jackpot, then a more substantial gift – some nice green cash, perhaps – is in order. And if it goes belly up? Well, don't say we didn't warn you.

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.

by JEANNE FLEMING, PH.D. and LEONARD SCHWARZ

Question: Friends always hold a lavish holiday party, which we enjoy attending. Another regular guest is a wealthy neighbor who is facing securities fraud charges, charges that are clearly well-founded. Must we chat pleasantly with this man, or is it okay to convey by way of our frosty manner that we're disgusted by his dishonorable behavior?

Answer: Why stop with the cold shoulder? Why not a slap in the face with your glove?

Seriously, we’re as offended as you are by white collar crime and the people who commit it. But until a person stands trial – until the prosecution presents its case and the person accused of the crime has an opportunity to defend himself – you shouldn’t rush to judgment. Once the evidence is in, though, feel free to let the judgment flow. And if what you learn convinces you that this guy is a crook, there’s no reason you shouldn’t treat him as one, regardless of how your friends behave toward him.

What you mustn’t do, however, is use a friend’s party as an opportunity to act out your disapproval. When you accept an invitation to someone’s home, you have an obligation to be pleasant with all the other guests. If you aren’t willing to do this, you should decline the invitation. You might even want to tell your hosts why, in the hope they’ll reconsider before again extending their hospitality to this man. But making a friend’s guest feel uncomfortable, while not in a league with securities fraud, is still out of bounds.

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.

by JEANNE FLEMING, PH.D. and LEONARD SCHWARZ

Question: We own a vacation condo we’ve always been happy to lend to friends. Lately, though, we’re constantly being asked for it, which has begun to interfere with our own plans. Plus, the wear and tear from these visits is taking its toll. Would we be wrong to charge rent in order to discourage friends from abusing our hospitality?

Answer: Not at all. Look, there’s a name for friends who systematically help themselves to what others have paid for, and it’s freeloaders. Whatever these folks who are imposing on you may imagine, you’re not obligated to provide them with a vacation getaway.  On the contrary, asking them for some rent is ethical, fair and honorable – unless, of course, you’ve invited them there as your guests.

Presumably, of course, you neither want to overcharge your friends nor offer a bargain that’s irresistible. So talk to a realtor about what condos like yours rent for and what the typical “family and friends” rate is. Then think about whether you want to charge different people different rates based, perhaps, on how close you are to them or how much they can afford. Be forewarned, though, that while there’s nothing unethical about a sliding scale, it could lead to friction.

And brace yourself for another source of friction as well: Nobody likes a take-back. Instead of being as appreciative as they should be of your generosity, some of your pals – the true freeloaders – may get angry when you ask them to contribute. Of course they have nothing to complain about – but when did that ever stop anybody?

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.

by JEANNE FLEMING, PH.D. and LEONARD SCHWARZ

Question: When I needed money to get my restaurant started, my good friend Dave lent me $12,000 with the proviso that I hire his son, who hopes to be a chef someday.  The kid’s been working in the kitchen for three months now, and he’s all thumbs.  Is there anything wrong with firing Ryan, or am I stuck with him until I pay off the loan, which won’t be for another year?

Our answer: A deal is a deal.  So whether you’re stuck with Ryan hinges on exactly what the deal was you struck with his father.  If, in return for the twelve grand, you promised to give Dave’s son a try-out in your kitchen, then you’re free to tell the Platebreak Kid to turn in his toque. 

But if you effectively promised to give Ryan the opportunity to learn his craft - and it sure sounds as if that’s why Dave lent you the money – then the fact that the kid’s a disaster doesn’t get you off the hook. 

Were Ryan stealing from you, of course you could fire him.  Were he lazy and disrespectful, you’d be within bounds to insist that he shape up or leave.  But being a klutz isn’t sufficient grounds for letting Ryan go - not if Dave believed the loan guaranteed an apprenticeship for his son.

And what if you and Dave never discussed the exact terms of Ryan’s employment?  In that case, try to err on the side of keeping the kid.  After all, your friend did you a big favor.  You should try to do him one in return.

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