We all want to help the people we care about, but when it comes to money, things can get messy real fast.

In this episode of the DollarsAndSense Podcast, Timothy and Dinesh get real about what usually goes wrong when you lend money to friends or family, from unspoken expectations to awkward silences when repayment time comes around.

They share honest takes, real examples, and how to navigate this tricky territory with clarity, boundaries, and care. Because sometimes, saying “no” might be the kindest thing you can do.

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