A friend or family member owes you money. How do you get it back?

We've often heard that loaning money to a friend or family member can make things really awkward – especially if you don't get paid back.

Sometimes it's not even something official or a direct ask: maybe you paid for dinner when the other person was short on money or forgot a credit card.

But then time passes and it's crickets about paying you back.

So what do you do when someone owes you money – and it has gotten very uncomfortable?

Welcome back to Uncomfortable Conversations About Money, a recurring series where we will tackle challenging topics or situations around money that make you uneasy. We'll outline the problem and try to get you some usable solutions.

Money owed sours friendship

The dilemma: Ron Anderson helped out a friend in need. But things got so uncomfortable between the two when the friend didn't repay the money that they didn't talk for nine years.

In 2015, Anderson was on vacation with his family when he got an urgent call from a college friend. The friend was at a resort with his wife and her parents and said he lost his wallet. He couldn't pay for the resort.

"So he was a bit embarrassed and he felt like he needed some help," said Anderson, 56.

At the time, there weren't peer-to-peer payment apps, so Anderson called his financial adviser to wire money to his friend. Anderson sent $800.

"I sent that to him and he says 'Listen, I'm going to get that back to you. I'm going to send it to you,'" Anderson recalled.

For the next week or two, there were supposedly some efforts to send the money back to Anderson, "but it never kind of materialized or never came through for whatever reason," he said. "There was always some kind of issue that came up or some kind of problem."

Anderson said he didn't hound the friend or ask "Hey, where's the money." While Anderson wanted the money back, he said once he realized he might not get it, he didn't bring it up.

Yet Anderson said when he loaned the money, it was not a gift but was given with the expectation that he would get it back.

"I just felt, I guess, taken advantage of in a way," Anderson said of the friend. "I think I used this term with my wife afterward: I felt like he kind of bought himself out of our relationship."

The two men didn't talk for nine years. A mutual acquaintance who was in contact with the friend told Anderson that the friend was embarrassed about owing him money.

Be upfront about the money owed

The expert advice: My expert this month is Myka Meier, founder of Beaumont Etiquette in New York City.

"It's a very common situation where people feel very uncomfortable about asking for money or even talking about money. It has a taboo attached to it," Meier said.

It's also true that many people have found themselves in a situation like Anderson's. A study by Paypal this fall found that one-third of people, or 33%, have hesitated to request money owed to them to avoid feeling cheap, pressuring friends or family, or because they did not want to coordinate payment logistics.

The study found on average, people are owed $926, from friends or family.

People are afraid of being awkward or being pushy, but it doesn't need to be like that, Meier said.

"It's something that can be very easily navigated by using communication, being very open and upfront and talking it out," she said.

Pay back money as soon as you can

Proper etiquette is to pay somebody back as soon as you know that you owe the money, said Meier.

"So if you do owe somebody else, then it's hopefully not getting to the point where they do have to ask you or remind you," she said.

"But if you are the person that is owed money, you shouldn't be afraid to ask that person or to remind them," Meier said. "It's OK to gently remind them. If you make something a big deal, it becomes a big deal.

"Sometimes people get busy and it sometimes happens where we forget or it slips our mind," Meier said.

But what should you do when it's gone way beyond a few weeks – and perhaps turns into years, like in Anderson's case?

"It's such a shame to let money get in the way of a friendship or family," Meier said. "But I think in that situation, written communication is preferred for me. Since it's in writing, it's much harder to forget."

Email is more formal than a text, Meier said. If it's one person in a group of people who still owes you money and the other people have already paid, Meier said emailing everyone in BCC (blind carbon copy) about a reminder to pay "doesn't pinpoint that one person, which can feel awkward."

If someone is in a situation where they need the money back and aren't able to wait longer, telling the person "let me know when you think you might be able to pay me back," could be a good opportunity for communication, Meier said.

Meier said it's also OK to say no to loaning the money or picking up a tab in the first place.

"I think it's absolutely fine to be upfront and not feel pressured to have to put the money up," she said.

About that money owed...

Postscript: Anderson and his college friend have recently reconnected. Anderson, who remained Facebook friends with his old schoolmate, liked a comment and the friend called him out of the blue.

They talked for more than two hours and again the next night.

"At one point during the first conversation, probably an hour or so in, he did reference the money. I did not bring it up. He said, "Hey, listen, I do still plan on paying you back."

Anderson said he told him he wasn't worried about it, but also didn't say he wasn't interested in getting paid back.

Uncomfortable Conversations: Did you get stuck splitting the dining bill unfairly?

In hindsight, Anderson said he probably should have reached out earlier to say "Hey, listen, don't worry about what happened. Let's just restart."

"We did lose nine years. Regardless of money, that's not worth it really in hindsight," he said. "But I guess there was I'll say pride or ego or hurt feelings on my part that prevented me from doing that."

Anderson's advice to others who have lent money to friends or relatives and haven't been immediately repaid: "You should really consider it a gift, even though it's stated as a loan. You need to consider, listen, this may not turn out well.

And then, if the money is indeed never paid back, think about "how much is that really material in your overall relationship holistically?"

We want to hear from you

Do you have an Uncomfortable Conversations about Money topic you'd like to suggest? Or would you be willing to be featured in a story about your Uncomfortable Conversation? Email blinfisher@USATODAY.com with "Uncomfortable Conversations" in the subject line.

Here are some upcoming topics: Have you received a holiday gift and you didn't have something to give in return? What should you do when your spouse or partner's ex asks for money?

Betty Lin-Fisher is a consumer reporter for USA TODAY. Reach her at blinfisher@USATODAY.com or follow her on X, Facebook, or Instagram @blinfisher. Sign up for our free The Daily Money newsletter, which will include consumer news on Fridays, here.

This article originally appeared on USA TODAY: What should I do when a friend, family member owes me money?