‘That really ruins Thanksgiving dinner’: Here’s what Kevin O’Leary does when family members ask him for money — he gives it to them on ‘one condition and one condition only’

“Family member comes to me and says 'Look, I want to build a restaurant. I need you to give me $150,000 to get started.' I don’t want to go into partnership with somebody in my extended family,” he says. “That really ruins Thanksgiving dinner.”

Nevertheless, O’Leary says he has a simple strategy to deal with these uncomfortable requests for financial aid.

Make it a one-time gift

When a family member asks for money, O’Leary says instead of investing in their venture or loaning them money, he offers them a gift instead.

"What I say is 'Look, you've never asked me for money before, I'm going to give you, in that case, $50,000. It's not a loan, it's a gift. I never want it back from you,'" he said.

However, this gift comes with an important caveat: they can never request money from him again, ever.

The key lesson here is that people who get frequent requests for money should adjust the expectations of their friends and family.

A 2022 poll by CreditCards.com found that 59% of those who have lent money or paid for a group expense with the expectation of being paid back had a bad experience with it. Forty-two percent of the lenders were not repaid, and 26% said their relationship with the borrower was damaged. Worse still, 10% of the respondents said it resulted in a negative impact on their credit scores and 9% said they had a physical altercation with the borrower.

You should help when you think it's appropriate, particularly when someone close to you is in dire need, but keep in mind financial support to friends and family can have emotional and financial consequences.