Can You Pay Me Back?

3 ways to ask for your money back without making it weird

Something weird happens to me when I have to ask someone to pay me back.

After spending too long trying to craft the perfect text message, I nervously send something like this:

Hey 👋
[This emoji says I’m chill, right?]

Great to see you last week!
[Just affirming that our friendship is more important than money!]

Just thought I’d check in about your share of the hotel bill!
[But I am toooootally not thinking or worried about it at all. ]

Thanks!
[Not actually sure why I’m saying this!]

While this affliction may disproportionately affect people-pleasers, I know that asking someone to pay you back is complicated for a lot of us—even (especially) when it’s with family and close friends.

I asked a few folks here at YNAB how they handle it when someone owes them money and why it can feel so hard to navigate. Here’s what they recommended:

Tactic 1: Clarify expectations upfront

If it feels awkward to ask for money, it might be because you’re not 100% sure what was actually agreed to.

My colleague Kathleen finds that clarifying the agreement solves most of the weirdness. Ideally, the conversation happens before the payment happens. Expectations are spoken ahead of time like: who’s covering what? When is repayment expected and how will it be sent?”

When everyone is clear going in, there’s nothing weird about following up later. You’re not “asking for a favor,” you’re just closing the loop on an agreement.

So speak up and confirm the details you need! Even a simple, “Just making sure we’re on the same page—you’ll send your half by Friday?” can make a huge difference.

Tactic 2: Let Venmo do the talking

Kathleen again, “I send Venmo requests, and it’s key to send the request as soon as it’s warranted. If someone owes me for dinner, I send the request that evening. Waiting a day or two or longer makes it more awkward.”

Sending a request through Venmo, bank, or e-transfer in Canada, makes it clear what you are asking for and easy for the other person to pay right then. This is a good option if you are exhausted by trying to strike the right tone of asking for what you want, but also pretending you totally don’t care.

Tactic 3: Eliminate expectations altogether

It surprised me, but several folks at YNAB said they never loan money or pay for dinner unless they’re okay with not being paid back at all.

Hillary wrote, “If I do get paid back, wonderful! If not, it’s fine because when I loan money or pay for something for someone, that money is gone. I know my financial situation is very different than friends or family, and that this is a privileged position. But when I wasn’t in this position I just wouldn’t offer to pay or would say, hey, I can’t cover both our parts.”

A related version from Ashley G: “Sometimes I say, ‘Hey! Did you want to Venmo me for dinner last night, or do you just want to cover it next time we go out?’”

I was impressed by the thoughtful and straightforward responses from my coworkers. I also had the sense that talking about money is profoundly difficult if you think there’s a way you’re supposed to do it.

I keep thinking of the Barbie movie monologue, in which Gloria (America Ferrera) lists the many conflicts of being a woman: “You have to be thin, but not too thin. And you can never say you want to be thin… You have to have money, but not ask for money because that’s crass.”

Talking about money is similar— it’s a collision of too many taboos for us to think we can do it in a ‘perfect’ way.

We live in a culture where talking about money is frowned upon, and yet almost everything in our lives interacts or depends on it. So, I say find what works for you (before the spending occurs, if possible). Say how you’d like to split it, or not split it. Resist the impulse to upset no one.

I’d love to hear from you: How do you usually handle the awkward art of asking someone to pay you back?

Until next time,

Dan