The sheer awkwardness accompanied with asking your friends to pay you back is the main reason I have so much trouble doing it in the first place. I have been in too many situations where I have paid for my friend’s lunch or an uber ride and never gotten my money back. I am always scared my repeated asking will affect my friendship with the other person. However, over time, I have learned a few tips and tricks to overcome this usually inconvenient situation.
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Ask them in person
Texting equals forgetting. Face-to-face interactions are more effective. A brief conversation with your friend compared to a single text will definitely help them remember to pay you back quickly.
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Let them get the next round
Your friend doesn’t necessarily have to pay you back in cash. The next time you go out, make them pay for your dinner or your uber.
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Politely remind them
A polite reminder every so often doesn’t hurt. Sometimes people genuinely forget to do things. Keep in mind to use specific language that conveys your courteous attitude: ask your friend when it would be convenient for THEM to pay you back.
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Be direct
At the end of the day, it is always helpful to be direct. It’s simultaneously the easiest and most difficult way to get what you want. However, it is important to remember that the likelihood of your close friend being offended from your persistent attitude is close to zero. If they are truly your friend, your relationship won’t be affected at all by a couple of bucks!