Wait, don’t pick up that check again!

When it comes to dealing with freeloading friends and deadbeat relatives, Jeanne Fleming and Leonard Schwarz suggest that you be what they call the three P’s: prompt, polite and pointed.

All too often, people get taken advantage of for no better reason than that cheapskates think they get away with it, according to the husband-and-wife writers, who pen a money and ethics column for Money magazine.

“There’s no indication that these are people who are down to their last dollar,” Schwarz said. “Every indication is that they are people who feel no moral obligation to pay.”

The authors, whose book “Isn’t It Their Turn to Pick Up the Check?” was published last month, have categorized the people their readers consistently complain about into several character types, along with suggestions for dealing with each of them.

The deadbeat

An Internet survey conducted by Schwarz and Fleming indicates that 95% of adult Americans have lent money to a friend or family member, and 36% have made a loan of $1,000 or more. When asked about the largest such loan they had made, 43% said they hadn’t been paid in full -- and 27% hadn’t been paid at all.

Women are more likely to be stiffed than men, and poorer lenders are less likely to get their money back than those earning $100,000 or more, the survey found. That suggests skipping out on a debt isn’t so much about what the borrower can afford but rather how vulnerable the creditor is perceived to be.

“The decision not to pay,” Schwarz said, “is often the result of a cynical analysis of the person that they owe money to, rather than a sense of desperation.”

Fleming added: “It’s more about borrowers’ calibrating whether they can get away with it.”

How can you avoid getting skipped out on? Three tips:

First off, of course, be careful -- about whom you lend to and whether you can afford to make the loan.

“While it’s great to be generous and do good deeds, you need to be analytic about whether the person is likely to repay you and whether you can live without the money if they don’t,” Schwarz said.

Second, if you expect to be repaid, put the loan in writing. You might not need a long contract, but you definitely need a few lines documenting who lent whom what amount, and when and how that loan is expected to be repaid. (If nothing else, the Internal Revenue Service requires such documentation if you later want to write off a bad debt on your income taxes.)

Finally, if a payment isn’t made as stipulated, say something right away.

“If one month goes by and they don’t pay you, you had better ask why,” Schwarz said. “It doesn’t mean that you have to send somebody to break their thumbs, but you need to put them on notice that they need to pay you or explain. Otherwise they get comfortable not paying you back.”

The rathole relative

A special subset of the deadbeat is the chronic deadbeat relative: a family member who consistently borrows money that he never repays. One-third of those surveyed were familiar with this kind of relative.

Sometimes the nonpayment is a result of genuine financial problems. Often, however, the family member has plenty of money for luxuries but can never seem to pay the rent.

What do you do when you’re hit up -- again -- for a loan?

Know what you’re in for before getting in, Schwarz and Fleming suggest.

“You may decide that the love of your sister is such that you are willing to subsidize her behavior,” Schwarz said. “But if you do that, you should make it part of the decision.”

Some people try to put strings on these loans, saying, for example, that the money can be used only for rent or food. That might make you feel better, but Fleming called the strategy flawed because “money is fungible.”

“So you pay her rent,” Fleming said. “Now she can spend the rest of her money on bourbon.”

And if you fund a relative, you have to figure it’s like giving a mouse a cookie: The mouse will come back.

“You should realize that this is going to be a gift, not a loan,” Schwarz said. “And it is going to reinforce their behavior.”

The cheapskate

You and your three siblings decide to give an expensive present to your parents to celebrate their 50th anniversary. The problem: Everybody knows that one sibling won’t pay his fair share -- because he never does. He either pays a small portion and forgets the rest or never ponies up the cash at all.

Instead of splitting the bill by three and signing the card for four, Fleming suggests that you either ask for the money in advance and include the cheapskate only if he pays his share, or sign the card from the three of you.

“The kids who pay can just tell their parents that it’s a gift from them,” she said. “They don’t have to say anything bad about the brother.”

In other words, let the cheapskate fend for himself.

The overspender

The flip side of that problem is the family overspender, who is happy to pay an equal share of the tab but makes the cost unaffordable for everyone else.

Example: Instead of buying a gift, you’re planning an anniversary party for the parents.

One sibling volunteers to be in charge of wine, which sets off warning bells for the other three. Everyone else is happy with an inexpensive brand, but the overspender can’t imagine serving something that costs less than $50 a bottle. If you have 100 guests, the party bill begins to look like the national debt.

What do you do? Set a budget.

“If you have experience with a sibling who has more money than you do and you know they are going to get into this in a way that you can’t afford, you should be preemptive,” Fleming said. “Get everyone to agree on a budget in advance.”

The great thing about budgets is that they force expectations into the open, Schwarz added.

“You don’t have to go so far as saying we have a cheapskate versus an extravagant person. You can simply have different understandings about the level at which you want to do an activity,” he said.

If three of you agree that the budget calls for $10 bottles of wine, but that makes the fourth sibling unhappy, she can have the option of paying more to get what she wants. That keeps the budget in line for the other three while allowing the fourth to carry out her vision at her expense.

The moocher

You go out to dinner with a group of friends, including one couple who consistently pay less than their share. What do you do?

A. Let them get away with it, as they always do.

B. Stop scheduling these dinners because they leave you feeling used.

C. Tell the waitress you want separate checks.

D. Speak up and note politely but firmly that the cheapskate owes more.

Plenty of people opt for one of the first two choices, but either of the last two responses would be smarter, Schwarz and Fleming say.

The important thing, they say, is to speak your mind.

“Some people believe that they will be considered small if they stand up for themselves and ask for what’s theirs,” Schwarz said. “But we have to quit letting the thieves of kindness make us feel bad for counting. They are the bad guys, not you.

“You don’t have to be angry. You just need to say, ‘Gee, John. I think you forgot about the tip. I need you to kick in another $10.’ ”

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Kathy M. Kristof welcomes your comments but regrets that she cannot respond to every question. Write to Personal Finance, Business Section, Los Angeles Times, 202 W. 1st St., Los Angeles, CA 90012, or e-mail kathy.kristof @latimes.com. For past Personal Finance columns, visit latimes.com/kristof.