How to Ask Someone to Pay You Back (Without Making It Awkward), According to Etiquette and Money Experts

published Nov 3, 2021
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If you’ve ever lent a friend money and then faced the challenge of asking for it back some time later, you know how awkward that interaction can be. While digital apps like Venmo and Cash App have made it easier to pay someone back in the moment, there’s still the emotional matter of sending the request — because in reality, money can be a difficult conversation to have with anyone, let alone friends. 

“Money has been a taboo topic for a long time in our society and I think we are just now starting to talk a little more about it,” consumer and money-saving expert Andrea Woroch tells Apartment Therapy. And as she notes, that stigma can have an effect on friendships. “Because we don’t talk openly about money — how much we make, debt, expenses, et cetera — anything associated with it feels awkward, even if it’s asking someone who knows they owe you money to pay you back,” Woroch says.

Personally, I try to approach lending in my friendships in an organic, give-and-take kind of way — if I pay for one round of drinks, my friend can get the next, and so on. Other people ascribe to a belief that you shouldn’t loan money you aren’t ready to think of as a gift. But in certain situations, you need your money back. What to do if and when that happens? Here’s how to ask for someone to pay you back, according to etiquette and money experts.

Be direct.

Yes, it can be difficult to talk about money, but it’s important to push past the awkwardness if you can. According to etiquette expert Diane Gottsman, beating around the bush will likely only make things weirder. “Being direct is the best way to get a straight answer,” she says, adding that if you can, have the conversation in-person rather than over text, email, or phone call. “Face-to-face is always better because it’s more difficult to avoid someone that is looking you directly in the eyes,” Gottsman explains.

Julie Blais Comeau, the Chief Etiquette Officer at Etiquette Julie, agrees. It might seem easier to hide behind the comfort of a screen when asking for your money back, but she stressed that, “Money matters are not texting matters. There may be misinterpretations, especially in the tone,” she says.

Structure it as a statement and a question.

Sure, being direct matters — but how you phrase your request while asking for your money back is still important. While asking, you should make sure the person you are talking to understands why you are asking for your money back, as well as what kind of timeline you’re expecting for their repayment to you. 

Psychologist, educator, and author Alex J. Packer, Ph.D., suggests structuring the conversation by setting the context of why you are asking for your money back. He notes that a phrase like, “I would appreciate it if you could repay the loan I gave you. I am short of funds and need to ask you to pay me back,” is to-the-point and often effective. Afterwards, he suggests that you perform the “ask” with questions that set a definitive timeline. “When do you think you can pay me back?” “Can you pay me back now?” and “If you can’t pay the full amount, can we come up with a payment plan?” are all good ways to approach the idea of when.

Be understanding, without taking things personally.

While asking for your money back, you should be considerate of your friend’s potential financial situation, whether or not you know about it directly. Gottsman underlines the importance of being aware of income differences and priorities when it comes to spending. “Most people have a variety of incomes and being respectful of each other’s circumstances is the key,” she says. 

Of course, this advice goes beyond a specific instance in which one friend owes another money. “The key to successful friendships between people with different incomes is empathy,” Packer says. Money does not need to be a problem among friends if you can respect each other’s boundaries and priorities. 

It’s also important to not assign personal meanings to something as impersonal as money. Lauren Greutman, a frugal living expert and the author of “Recovering Spender,” suggests that you isolate yourself and your relationship while asking for your money back. “I would try to take the emotions out of it completely,” she says. (While etiquette experts advocate for in-person conversations, she suggests writing a letter or email.) ”You can get into your own financial situation if you wish, but I don’t believe that you necessarily owe it to that person,” Greutman adds.

If you aren’t seeing your friend in the near future and you’re on a tight deadline for that money, Woroch suggests approaching the ask casually and not putting too much meaning into it. 

“Send a text as a friendly reminder along with your account name for Venmo, PayPal or Zelle. I like adding personal messages such as, ‘Had a great time last night’ with an emoji and then a gentle reminder to pay you back X amount,” Woroch says. “It’s important to remember, people sometimes just forget to pay you back so you shouldn’t feel bad asking for your money back. Many people appreciate the reminders!”

Keep track of who paid last time.

With friends you see often, and whose financial situations are similar to yours, it may simply be easier to keep a mental note of who got the bill last and go from there. If you paid for dinner, there will be a time where they will pay in return. “Depending on how often you and a friend or group get together and split bills, you can take turns paying the bill,” Woroch says. “For instance, if you meet for lunch once a month, take turns covering the bill — rotate who pays. Just know that sometimes it may be more or less expensive so it may not completely even out.”

Let it go.

A common rule of thumb most money and etiquette experts swear by is to not lend money you cannot afford to lose. If the person you lended money to is not in the position to pay you back, it can often be helpful to the health of your relationship to let it go. “My general recommendation for lending money is to never lend any amount of money that you can never do without,” Blais Comeau says. “When you agree to lend money, mentally make that amount a gift. Put a nice bow on it and forget about it.”

Packer agrees, and notes that if you are financially able to do so, it can be healthy for the friendship to tell your friend you’ve had a change of mind. “Tell your friend that you recognize that times are tough, that you have been blessed with a degree of financial comfort, and that you would like to share that blessing with them,” he says. “Verbalize the value to you of her friendship, and how it would be a gift to you to help them out by forgiving the loan.”