How To Ask Friends To Pay You Back Without Giving Debt Collector

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 there aren't great examples of having tough conversations as proof that you are close with this friend. “Without examples of how to bring up money in a kind way, it can feel awkward, rude, or even make the asker feel guilty.”

But here’s the thing: asking for your money back doesn’t make you the bad guy. It makes you honest. “When someone reminds me I owe them money, I don’t take offense,” Bryan-Podvin says. “It’s a reminder that they feel safe enough to nudge me to repay them.”

To help you pull off that nudge, we asked financial experts how to ask for your cash back (without spiraling into anxiety or resentment).

Turn It Into A Joke

If you’re asking a close friend or bestie to pay you back, a little humor goes a long way. You know that Venmo note section? Time to practice your stand-up set.

“An inside joke or playful message can go a long way in making the ask feel less awkward,” says Bryan-Podvin. According to a 2024 Cash App money management report on how Gen Z manages money, 68% of people include a funny note when requesting payments from friends.

Stuck on what to say? Bryan-Podvin has some ideas. “As an eldest daughter and Virgo, I’d use that in a money reminder text,” she says. Try something like, ‘Just your friendly spreadsheet-loving friend doing her Virgo duties ♍! Please send me the $46 from last night’s dinner, xo.’”

Another hack Bryan-Podvin loves is using a Mad Libs-style format: “Remember [funny thing/memory that happened]? Speaking of, can you send me $X for [thing that happened]?”

Remind Them Why You’re Besties

Instead of making it about the money, make it about the friendship. “Reminding your friend that you share values can appeal to what you have in common and help center the relationship instead of the dollars,” says Bryan-Podvin.

She suggests something like, “I know we both like to keep things fair — can you send me your portion before the concert this weekend?” Or, “Ty for being my giggle partner in crime,” when reminding someone they owe you money for tickets to a comedy show.

Try The Direct Approach

Experts agree that being direct is the kindest (and least stressful) route. “There’s a difference between being blunt and being direct while being kind,” says Bryan-Podvin. In fact, in many situations in life (even dating!), being clear with someone is another way of being gracious to someone.

Most people will appreciate not having to guess what you might be thinking. “Being direct is a sign of mutual respect, and it reduces the risk of miscommunication or tension,” says Bryan-Podvin. “A simple, ‘I covered you last time, can you send me $X before we go out?’ works just fine,” she adds.

Keep It Casual

Yes, Venmo has a “remind” button. But you can only hit it once, and sometimes it feels too passive (or too aggressive, depending on the situation). Instead, keep it breezy.

“If you haven't mentioned it before, keeping the conversation light can help things feel less tense,” says Emily Blain, an accredited financial counselor and founder of Dream Big Financial Coaching. “You might say something like, ‘Hey, I haven’t seen a Venmo from you yet. Want me to resend the request?’”

Just because someone hasn’t sent you the money they owe you doesn’t necessarily mean they’re trying to avoid doing it, and that shouldn’t be your first assumption. If a friend genuinely did forget, they will appreciate a gentle nudge.

Deploy A Hail Mary

If you feel like you’ve exhausted every polite method possible, it could be time to set a boundary within the friendship. But this doesn’t have to feel like an ultimatum. “Instead, it’s about valuing yourself and your friendship,” says Bryan-Podvin. “This can look like, ‘I can’t cover [dinner/ride share/gift] until I get the money owed from last time. I care about our friendship, and I don’t want money stuff to add tension.’”

If you’re constantly dealing with a friend who is borrowing money and stalling paying it back, Blain says it could be time to reevaluate the relationship. Or, at the very least, reconsider doing anything with them that costs money, she says.

On the flip side, if you’re in a financially stable place, covering a friend once in a while can be a kind and empowering gesture. “This world and economy can be tough, and if you're able to help your friends out a bit without it hurting you, sometimes that can be a huge gift.”

But you should never feel obligated. If you have your bills paid and aren’t worrying about your finances, it’s up to you how to spend any extra money. “If you say no to a friend who is asking for money and they take it personally, they weren't a great friend to begin with,” says Blain.