There’s nothing worse than dropping your card at dinner or drinks, only to spend the next three weeks chasing down a Venmo like it’s your part-time job. Maybe your friend’s short on cash. Maybe they “forgot.” Either way, it shouldn’t fall on you to play debt collector.

Still, asking someone to pay you back can feel weird, even when it’s totally fair. “Money touches every aspect of our lives,” says Lindsay Bryan-Podvin, a financial therapist for Cash App and founder of Mind Money Balance . “Reminding someone they owe you money can bring up things like trust, respect, and even power dynamics, especially if there's an income or socioeconomic difference .”

Part of the problem? “Our culture views friendship as something that should always be light, easy, and fun,” Bryan-Podvin adds. And t

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