The Rules of Regifting

When it comes to gift giving, is honesty the best policy?

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Maple balsamic vinegar dressing. That's what Bruce Weinstein, a public speaker known as "The Ethics Guy," received from his brother-in-law this Christmas. And he utters a gagging sound to demonstrate his feelings for the object. "I thought it was a joke. I was ready for a snake to pop out of the bottle," Weinstein says.

So, when his brother-in-law asked pointedly if he liked it, what did he do? He responded via the "praise sandwich technique," buffering the truth with compliments. He thanked his brother-in-law for thinking of him, explained that he "can't really envision using this product" and concluded with additional thanks. Enter on the scene his mother-in-law, who commented that she'd love the dressing, and voila: a regifting success story.

[Read: The Worst Holiday Gifts.]

You might say the transactions here worked because of the transparency involved – Weinstein's brother-in-law was upfront that he would reclaim the gift had it missed the mark. But, according to Weinstein, the trick in dealing with such delicate matters is in being, well, delicate.

"Even if my brother-in-law had said, 'Don't sugarcoat it – just tell me straight,' it would still have been wrong to say the raw, brutal truth," Weinstein says. "There's no reason to say that."

So, when it comes to regifting, how honest should a regifter be? According to etiquette expert Diane Gottsman, the "safest way to handle a regift" is to be open about the situation. Say you received something you already own or don't need or simply doesn't match your style but might suit a friend – then pay it forward with a clear conscience.

[Read: How to Cope With Holiday Stress.]

But to Weinstein, complete transparency is unnecessary. The guiding principle in these matters, he says: Avoid hurt feelings. "Sometimes honesty is not the best policy," he says. "If you stand back and look at what makes relationships work and what's right to do, it's hard to make a fetish out of telling the truth."

For his part, Weinstein considers regifting a moral imperative. Citing "an ethical obligation not to be wasteful," he argues that regifting or donating something you've received will provide a lot more use in the world than it would by remaining untouched in your closet. If you're regifting, however, it's important to be careful. Weinstein advises recycled gifts go to someone in a different town or social circle than the original gifter. "It's best to make sure that the person you give it to is not likely to run into the person who gave it to you," he says.

[Read: What's on Dr. Phil and Other Experts' Shopping Lists?]

To avoid an awkward situation, Gottsman suggests noting who gave you any gifts you plan to regift. And remember, a regift is still a gift, which is to say that it should reflect some thought and taste, Gottsman says. Whether you're giving something you've received to a friend or to charity, you want to feel a sense of pride in what you're giving.

"You don't want to regift an ugly gift," she says, adding that these things are, of course, subjective.

Just look at Weinstein and his mother-in-law.

[Read: 10 Healthy Gift Ideas for the Holidays.]