Female boxer model with big fun pink gloves“Needing money” from anyone can put a knot in your stomach, for sure. It’s uncomfortable and makes you feel beyond vulnerable if you’re asking someone you know. But, beyond feeling awkward, you could get doubly screwed by hurting your relationships in addition to your wallet. And that works both ways: if you’re the one asking and if you’re the one lending.

So: how do you get your loved ones to cough up what they owe you without compromising your relationship? Try this:

  1. Talk in person. Don’t text, email, or call; it’s all too easy for faceless communication to be taken the wrong way. And she will have a harder time avoiding you face-to-face.
  2. Be specific. Chances are, she doesn’t even remember that she owes you money, or the specific amount. Regardless, don’t leave room for doubt by asking: “When do you think you’ll be able to pay back the $100 that I lent you?” You’ve named the specific amount, so you’re on the same page with what she owes, and you’ve asked for a specific timeline so you can hold her to it.
  3. Set a deadline. Some people need multiple reminders. That’s life. If she doesn’t pay you back right away, set a firm deadline for paying you back. Soften the ultimatum by referring to an upcoming event, such as, “You know, with my vacation coming up, I could really use that money I lent you. Could you please pay me back by Friday?”
  4. Offer flexibility. If your friend is having a hard time paying you back, or if the amount she owes you is more substantial, offer to break the repayment into smaller chunks.
  5. Pick your battles. Sometimes you have to decide what’s more important: getting your money back or remaining on good terms with your friend. If it’s a small amount, say $10 for cab fare, and you’re in the financial position to do so, let it go. It’s annoying, but pestering her over and over again could cause a rift in the relationship.