How To Ask Someone To Pay You Back Without Being Awkward

Banish “No worries if not!” from your vocab.

Two friends split the bill in a restaurant. Experts share their tips for how to remind someone to pa...
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Jamie, 29, is one of those responsible people who always hits up the ATM before going out — she doesn’t mind covering her friends when they’re out someplace that only takes cash. But she finds reminding friends to pay her back so “mentally taxing,” she’ll only follow up a Venmo request once before giving up on getting paid back entirely. “I wish I had the balls to look someone in the eye and ask to be reimbursed but it’s just too uncomfortable to me. Making things awkward is literally not worth the money to me,” she says.

Navigating money and friends can be complicated. Whether it’s a pal who forgot their wallet at brunch, or a roommate who is short on rent, you don’t want to say “no” to someone you care about when they ask you to spot them, but you also want them to pay you back on time. A 2018 survey of 9,000 U.S. adults from Zelle, an app where you can send and receive money, found that 28% of women will wait until someone sends them money for their portion of the bill rather than asking them to pay them back. The end result? 86% of women reported not being paid back after covering a shared expense, such as concert tickets or a meal for friends, with 16% of women saying or this happens “all the time.” Sound familiar?

Ella, 30, feels that financial favors should not only be considered gifts, but also resentment-free offerings. “If there’s a history of one-way lending with this person, or a chance it might ruin our friendship if they aren’t able to pay me back, I won’t offer to help in the first place,” she tells Bustle. “I realize that might sound cold, but it’s important to have boundaries when you’re mixing friends or family with money,” she says.

Lending money can put strain on a friendship,” Kathleen Grace, C.F.P., managing director at United Capital’s Boca Raton, FL branch, tells Bustle. “But if you are like most of us, we sometimes feel compelled to help a friend in need.” She says that if you are considering loaning a friend money, first have the mindset that you may never see it again. “In other words, consider it a gift,” Grace says. “This way, you will not be too upset should you never get all or a portion of the money back.”

But what about when that one-time Venmo request is just sitting in someone’s inbox? Here, money experts explain how to remind someone to pay you without making things weird.


How To Remind Someone To Pay You Back, Nicely

When it comes to asking a friend or family member to pay you back, Kimberly Palmer, personal finance expert at NerdWallet suggests keeping your request “short and sweet.”

“They may have simply forgotten that they owe you money,” she tells Bustle. “At the end of a conversation about something else, you can add, ‘Oh, by the way, did you want to pay me back for that money I let you borrow? Venmo or cash works for me.’” She also recommends being explicit about how much they owe you if you’re expecting them to Venmo you. “No one likes to get an unexpected request for money after the fact.”


Don’t Let Too Much Time Go By Before They Pay You Back

The longer you prolong asking someone to pay you back, the more uncomfortable it’ll be. “Try to get the money back as soon as possible,” Andrea Woroch, consumer savings expert, tells Bustle. “Otherwise, the IOU can put a strain on the relationship and friends or family may forget, making you feel more awkward to ask.”

She also says that you should never feel bad to ask someone to pay you back. “It’s money that is owed to you that you loaned out of goodwill with the intention of being paid back,” she says.


Make It As Easy As Possible For Them To Pay You Back

Melissa Lowry, vice president of brand and marketing at Early Warning, the network operator behind Zelle, believes that setting financial boundaries and expectations with friends and family can save your relationships. “If someone covers an expense for you — or you for them — you both want to be paid back as quickly as possible,” she says. “Apps make it super easy to request and send money — it’s totally appropriate to let people know they still owe you.”

In addition to suggesting your friend or family member pays you back via an app like Zelle, Venmo, PayPal, Apple Pay, and so on, you can also think of other ways to get them to pay you. “Offer to make it easy on the person by going to their home or work to pick up cash or a check,” Woroch says. “Or, you can provide your P2P payment details if that makes it more simple for the person to pay you back."


Ask Them To Cover A Meal The Next Time You Go Out

If you want to be a bit more subtle in your approach for reminding someone to pay you back, you can wait until you and your BFF are out again, advises Woroch.

“Depending on what the person owes you, ask them to cover you when you are out together for a meal and simply suggest they pay the portion they owe you,” Woroch tells Bustle. “Then, you cover the rest if there’s a balance.” She says that, this way, it’s casual and doesn’t put someone on the spot to come up with cash or a check.


Be Direct When You Ask To Be Paid Back

Asking someone to pay you back is not fun, but sometimes being direct and asking face-to-face is necessary. “If you’ve seen no movement on their part to pay you back, just ask,” Grace says. “Say, ‘When do you think I can expect to see a payment?’ or ‘Hey, can you electronically send me the money I lent you?’ or ‘Can we set some repayment schedule for the money you owe me?’”

While it can be uncomfortable to reach out to someone and let them know you’re still waiting to get paid back, there are ways to make the conversation free of tension for both parties. And often times, the person you loaned money to just forgot. “Don’t assume the person is ignoring you,” Woroch says. “People get busy, and if someone forgets to pay you back, don’t be on the attack right away. Give them a chance and call to politely ask for that money to be paid back.”

TL:DR? Before loaning a friend money, make sure you’re comfortable with asking for it back — and OK with potentially not getting it back.

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