My friends owe me money from 8 months ago—is it too late to ask?

My fiancé and I are about to be the winners of our friend group’s March Madness pool. The way things have shaken out, no matter which team triumphs, one of us is certain to win the pool — a victory for our joint wedding fund either way.

But as I was calculating our eventual winnings, I had a realization. I also commission a fantasy football league that I did not, in fact, win. I’d paid the prizes to the winner and runner up back in December, but had I collected everyone’s entry fees?

A quick scroll back through my Venmo account revealed that I hadn’t. Several friends, it turns out, hadn’t paid before August’s draft or anytime thereafter. It’s now eight months later, and I’m down a few hundred bucks, which raised another question: Is there a statue of limitations when it comes to hitting people up for money they owe you? Am I too late?

Not according to etiquette experts.

“I don’t think anyone who’s in the position of being the unwitting lender should ever feel awkward or uncomfortable about asking for something which is rightly theirs,” says Thomas Farley, an etiquette expert known as Mister Manners and author of the Mister Manners Mondays newsletter.

Nevertheless, asking for your money back after a long period requires some tact, etiquette pros say. After all, you’re just out to get what’s yours — not to appear petty, embarrass anyone or hurt their feelings.

Before taking any action, Farley says, remember that you and your friend are unlikely to be thinking the same way about the money. While those who are missing money are likely to have an “elephant-like” memory as to what’s owed, Farley says, “the recipient of that money often forgets super quickly.”

In many cases, once you ask, “they’re going to be mortified,” Farley says. “And if they’re good people, they’re going to remedy that immediately. So I wouldn’t hesitate. I think it’s all in your approach.”

Of course, that only applies if it is a legitimate debt. Asking your friend for $6 for a beer you bought them last July is going to come across as tacky, Farley says.

In cases like my fantasy league, in which multiple people owe me money, there are a few dos and don’ts, says Diane Gottsman, a national etiquette expert and owner of the Protocol School of Texas.

Sending a blanket email to let people know they still owe you can be a good first move, but it’s important to avoid calling specific people out in front of the group to avoid embarrassing anyone, she says. Another no-no — especially after some time has passed — is just sending a request for the money, sans context, on Venmo.

“If we went to dinner and you picked up the check, and now it’s three days later, that’s fine — it’s a quick reminder,” Gottsman says. “If it gets to be too long, though, that’s going to feel passive aggressive.”

Your best bet in most cases, she says, is to reach out to your friends individually. If it’s the first time in a while, framing things as a “friendly reminder” might get the job done.

The more times you have to follow up (and you shouldn’t be afraid to) you should be more forceful in your demands while remaining upbeat, Gottsman says. She recommends giving a deadline and a method of repayment, for instance: “Hi Sarah. I hope you’re doing well. I’m following up about the money you owe me for XYZ. Would you please Venmo me by Friday?” 

If it’s a large amount of money, or if your friend is struggling financially, you might talk with them about a payment timeline or paying you back in installments, Gottsman says. Doing so, even if it’s uncomfortable, is still within the bounds of good etiquette, she says: “As nice as we want to be, we have to be clear and we have to be politely firm.”

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