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?
THE GROUND RULES
Talk in person. Don’t text, email, or call; faceless communications are too easily misread.
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.
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.
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.
Provide a deadline.
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.