Excerpt: Isn't It Their Turn to Pick Up the Check?

Jan. 8, 2008— -- Money is generally a taboo subject among friends and family -- that's why it's so hard to deal with the touchy topic.

What do you do with a family member who's a cheapskate, moocher or a deadbeat? Should you lend money to friends who waste their own cash? How should you deal with money issues like these when they involve your loved ones?

Jeanne Fleming and Leonard Schwarz, authors of the new book "Isn't It Their Turn to Pick Up the Check?: Dealing with All of the Trickiest Money Problems Between Family and Friends -- from Serial Borrowers to Serious Cheapskates," joined "Good Morning America" to share their tips for dealing with those awkward money moments.

Fleming and Schwarz also write the "Do the Right Thing" column on money, ethics and relationships for CNNMoney.com and Money Magazine.

You can read an excerpt from "Isn't It Their Turn to Pick Up the Check?" below:

"Happiness is having a large, loving, caring, close-knit family in another city."—George Burns

We haven't come across any research to this effect, but we'd be willing to bet that, when Neanderthals roamed Northern Europe, there were always a couple of guys on the hunt who inevitably grabbed the choicest cuts of reindeer and acted as if they hadn't taken anything special. We'd also bet that each tribe had a guy who was always quick to consume his own berries, then kept asking others if they wanted all of theirs. And finally we'd bet that every Neanderthal at some point had to deal with a friend who borrowed his best spear, returned it with the tip chipped, and said "What could I do? My son was playing with it, and you know how kids are."

Perhaps a few of these characters got the clubbing they deserved, but their genes most definitely survived. Listen to people today talk about their big family holiday dinner and, no matter how wonderful it was, you still hear about the aunt who went cheap on presents for the kids, the sister who thinks bringing pies exempts her from helping in the kitchen, and the brother-in-law who single-handedly drank all the hosts' good Scotch—a fifteen-year-old single malt that he would never dream of buying for himself.

Every family today includes some otherwise perfectly fine people who are simply off when it comes to money matters. While most of us try to rise above our relatives' flaws, that can be tough to do. Your resentment grows, your wallet suffers, and—having not been confronted on his or her bad behavior—your relative continues to misbehave.If -there's good news here, -- it's that -you're not alone—everyone has a couple of thoughtless or selfish relatives. Meet a few of the classics.

My brother bought a new car instead of repaying the loan I gave him.

When a relative cheats on your kindness

Question: A year ago, I lent one of my younger brothers $3,500 when his employer went bankrupt. Josh agreed to pay me $150 a month until the loan was paid off, and he has never been late with a payment. But six months ago Josh landed a well-paying new job, and last weekend he arrived at our parents' 35th anniversary barbecue in a brand new SUV.

When someone sells a family treasure

Question: When my mother died, she left her very beautiful engagement ring to my sister. Carol, who didn't particularly care for the ring and who prides herself on being unsentimental about family, promptly sold it on eBay. My other sister and I are heartsick about this. Since the ring was a family heirloom, didn't she owe it to us to first ask us if we wanted it?

User (person who takes 45% 35%
advantage of others)Corner cutter 42% 37%
Greedy in his or her dealings 40% 29%
Dishonest in his or her dealings 38% 26%
Moocher 36% 32%
Freeloader 35% 26%
Deadbeat 35% 22%
Source: Fleming & Schwarz survey.

So if you've ever wondered whether you're the only one who has to deal with a brother-in-law who always sticks you with the tab, a cousin who never repays a loan, or a friend who never refills the gas tank when he uses your car, wonder no more. These guys are everywhere.

Must I give my misguided brother investment advice he needs, but doesn't want to hear?When a family member is about to do something stupidQuestion: My brother, a successful dentist who fancies himself a hotshot investor, recently bragged that he's about to buy a large parcel of undeveloped land. I'm a CPA, and I happen to know a bit about investing in raw land. I also know that my brother has no idea of the risks associated with this type of investment—in particular, how illiquid it is. Am I obligated to tell him, even though I'm sure the last thing in the world he wants to hear is his big sister warning him, yet again, that he's being foolish?

Answer:Why is it such a thankless task, saving the people we love from their own worst impulses? Fortunately, we're rarely obligated to do so. Your brother's an adult, and adults are entitled to make their own decisions and their own mistakes. In fact, once they both grow up, big sisters need to let their little brothers do just that. Only two circumstances obligate you to give your brother your opinion: if he asks for it, or if you think he's about to seriously jeopardize his family's financial resources.

Obviously you're off the hook on the first count. So unless you're worried a genuine calamity is about to occur—unless your brother tells you he's betting the ranch on this one, or your sister-in-law turns pale each time he brings it up—you can in good conscience keep your advice to yourself.

And who knows? Maybe if you withhold your opinion, your brother will find himself missing your good counsel instead of resenting it.