My fiance and I are trying to be the winners of our friend group’s March Madness pool. The way this situation plays out, no matter which team wins, one of us will definitely win the pool, making it a joint marriage fund win anyway.
But when I was calculating my final prize, I realized something. We also commissioned a fantasy football league that we didn’t actually win. You paid prizes to the winners and runners-up in December, but were you able to collect everyone’s participation fees?
A quick scroll through my Venmo account revealed that it still wasn’t. It turns out some of my friends didn’t get paid before or even after the draft in August. Eight months later, I’m a few hundred dollars down, and now I have another question. Is there a limit to hitting people to get money they owe? Is it already too late?
Not so, according to etiquette experts.
“I don’t think people who are unwitting lenders should feel awkward or uncomfortable asking for something that’s supposed to be theirs,” says Thomas Farley, an etiquette expert known as Mr. Manners and author of the newsletter Mr. Manners Mondays.
Nevertheless, asking for a refund after a long period of time requires some tact, etiquette experts say. After all, you’re just trying to get what’s yours. Don’t seem mean, embarrass anyone, or hurt their feelings.
How to claim unpaid money
Before you take any action, Farley says, remember that it’s unlikely that you and your friend think the same way about money. People who lose money are likely to have an “elephant-like” memory of how much they owe, while “the person who receives that money often forgets it pretty quickly,” Farley said.
In many cases, once a question is asked, “they’re mortified,” Farley said. “And if they’re good people, they’ll fix the problem right away. So I wouldn’t hesitate. I think it all depends on your approach.”
Of course, this only applies if the debt is legitimate. Mr. Farley said asking a friend for $6 for a beer he bought last July would be considered in bad taste.
In situations like my fantasy league, where multiple people owe me money, there are some do’s and don’ts, says Diane Gottsman, national etiquette expert and owner of Protocol School in Texas.
Sending a blanket email to let people know they still owe you may be a good first move, but it’s important to avoid calling out specific people in front of the group to avoid embarrassing anyone, she says. Another no-no is sending money requests on Venmo out of context, especially after some time has passed.
“If we go to dinner and you get your check and it’s three days later, that’s fine. It’s a simple reminder,” Gottsman says. “But if it lasts too long, it becomes passive-aggressive.”
In most cases, she says, your best bet is to reach out to your friends individually. If it’s been a while, framing things as “friendly reminders” might help you get the job done.
The more times you need to follow up (and you shouldn’t be afraid to follow up), Gottsman says, the more forcefully you need to make your request while remaining upbeat. She recommends specifying a deadline and repayment method. For example, “Hello Sarah. I hope you’re doing well. I’m looking into the money you owe XYZ. Could you Venmo me by Friday?”
If it’s a large amount, or your friend is struggling financially, talk about a payment schedule or installments, says Gottsman. She says it’s within good etiquette to do so, even if it’s uncomfortable. “No matter how nice we want to be, we have to be clear, we have to be polite and firm.”
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