As much as no one really treasures the experience of having to ask a loved one or friend to borrow money, we’re sure probably no one relishes the idea of asking someone to pay you back that money they borrowed.

If you know it’s gonna get awkward, the best solution is, of course, don’t lend money in the first place, Peter Post of the Emily Post Institute tells CNNMoney. But also? We’re human and often we do want to help out a friend in need.

So how do you get your cash back? It’s not like you can appeal to a customer service representative (actually, that’s not a bad idea…)

Here are a few tips CNN covers that could be helpful:

No faceless communication: Yes, it’s hard to confront someone in person. But gird your resolve and stick to personal interactions, instead of texting or emailing. Invite the pal or relative to hang out for coffee or a beer, suggests Randy Cohen, author of Be Good: How to Navigate the Ethics of Everything.

Use a lead-in: “So I was totally cool lending you money when [insert whatever happened here, the reason the person needed cash] because you’re my friend.” It’s a gentle reminder that you’re nice and that you know the other would do the same for you if you ever need help. And you might, because no one is perfect, right? If so-and-so gets mad at you for this, then well, that’s not cool

Cut to the chase: “When do you think you’ll be able to pay me back that money I lent you?”
Beating around the bush is just prolonging the awkwardness. You’re simply asking a question about a factual event that happened. Just do it, says the expert.

A timeline can be useful: “Hey so, it’d be great if you could pay me back before October.” Of course, no saracasm here. Outlining a deadline makes it a finite loan, not something that could drag on forever.

For more tips, check out the source link below. Or just don’t lend anyone a brass penny.

How to ask a pal or relative to pay you back [CNNMoney]

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