How to Ask a Pal or Relative to Pay You Back

As far as unpleasant tasks go, asking a relative or friend to repay a loan ranks up there with getting your wisdom teeth pulled or spending a weekend alone with your in-laws.

The best way to avoid this awkward conversation?

"Don't lend money to friends in the first place," says Peter Post, director of the Emily Post Institute. Of course, that advice isn't going to help if you've already ponied up the cash. Here's what will.

THE GROUND RULES

Talk in person. Don't text, email, or call; faceless communications are too easily misread. Instead, invite your friend or family member to chat over coffee or a beer so the atmosphere is more relaxed, says Randy Cohen, author of Be Good: How to Navigate the Ethics of Everything.

Let the relationship guide you. Decide what's more important: getting your money back or staying on good terms with the borrower. If you care more about the person than the cash and you're in a position to do so, you may be better off forgiving the debt.

YOUR BEST APPROACH

1. Opening gambit. "I was happy to lend you the money when you needed it. That's what friends do."

The strategy: You're gently reminding your pal that you came through when he or she was in trouble.

"Putting it this way shows you sympathize with your friend," says Cohen. "Chances are, the person feels bad about not paying you back. An understanding tone decreases your chances of a hostile response."

2. Be direct. "When do you think you will be able to pay back the $500 I lent you?"

The strategy: Hinting will get you nowhere, says Philip Galanes, author of Social Q's: How to Survive the Quirks, Quandaries, and Quagmires of Today, because the person may misunderstand (perhaps willfully) what you're asking.

Like ripping off a Band-Aid, the process will be less painful if you do it quickly and directly.

Start off nicely; getting angry is more likely to result in the borrower pushing back than if you stay calm.

"There's no sense in starting Defcon 3," Galanes says.

3. Add urgency, as needed. "We're going to get hit with some really big tuition bills soon and could really use that money."

The strategy: Of course, you don't need to justify asking for your money back, but it can be helpful to cite a pressing reason -- as long as it's true.

"Evoking a specific thing makes repayment seem more like a necessity than simply an option," says Cohen.

4. Provide a deadline. "I'd really like to get the money back before the end of June."

The strategy: Specifying a schedule for payback is crucial. Otherwise, the loan may hang out there indefinitely, even if the borrower has given lip service to paying you back -- and you'll just have to revisit the conversation at a later date.

5. Offer flexibility. "Would it be easier for you to pay me back over time, say, $100 a month?"

The strategy: If the borrower pushes back or you know he will have a tough time coming up with the cash, etiquette expert Cynthia Lett suggests breaking repayment into smaller chunks or reaching another compromise.

After all, you must really care about this person; otherwise, you would never have lent him the money.