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Third, inform your spouse from the get-go, and if you’re giving money to a child, find a way to treat his or her siblings equally. Resentment springs forth gladly from all sorts of sources: Who knew that Suzie, with her nice house and high-powered job, would feel injured when Dad helped her brother?

Fourth, if you can’t make the handout a gift and insist on seeing it as a loan, put the thing in writing. All the professional guides will tell you that this is the most important tenet of lending to friends and family. As Blair E. says emphatically, four years after he stuck his neck out for his farmer friend, “Just document it.” No matter how crass or untrusting it might seem, the experts want you to formalize an agreement. “You can lie and say, ‘I need it for tax purposes,’” says Blair, wishing he’d done so. “You’re not asking too much to ask for a piece of paper.”

To me, this sounds excruciating. You might as well say it straight out: “I love you, baby, but you’re a loser; your future looks iffy.” Or how about, “Darling, I would never leave you—as long as you sign here and don’t miss a payment”? But the point is to separate the emotional ties between individuals—which can exist as beliefs and longings and surges of affection—from the monetary ones, which are expressed as amounts and timetables and quantifiable obligations. They are two different connections that must exist as two separate realities. Writing out an agreement as a promissory note, including dates and interest rates if you want to charge them, will keep those ties from crossing and snarling.

Asheek Advani has created an ingenious system to make these transactions less awkward. His company, founded four years ago, offers a cheap, easy way to take the love out of lending, without being heartless about it. When someone hits you up, you can say, “Sure!” and send them to Circlelending.com. There, a combination of web pages and phone calls with a Circlelending staffer will provide options for structuring the loan. As a third party, the company will establish amounts, interest rates, and most important, a payment plan. It will even make automatic withdrawals and deposits, so that a deduction from the borrower’s bank account—every month, or quarter, or year—gets electronically transferred to the lender’s. “A piece of paper may get you clarity on amount,” says Advani, “but it’s the repayment plan that matters.” Circlelending even tallies up the fees for late payments and works out a new schedule if things go haywire. And the price is sweet: After an initial fee in the hundreds, you—or your borrower—pay nine bucks a month.