How do you ask a friend to pay you back without making it awkward?

Send a simple text so it is low pressure and clear. Make it about your situation and be specific about the amount and a date. Example message: Hey, quick reminder about the $60 I covered last month. My budget is tight this week, could you send it by Friday? Venmo, Zelle, or PayPal works, and if Friday is rough let me know what day works.

If they hesitate, offer an easy plan like two smaller payments on their next paydays. Once you agree, send a payment request with the amount and the agreed date in the note so they can just tap and pay. If there is no response, do one polite follow up a week later and say you need it by a specific date, then stop lending until it is settled. For next time, set a due date before you lend and send the request the same day to keep it simple for both of you.

This gets asked every week. Stop making it a whole production. The awkwardness comes from you tiptoeing around it. Money is not a vibes check. You lent it, you want it back. Use the search bar next time.

Send them a message with the exact amount and a date. Keep it in writing so nobody forgets and nobody rewrites history. If they dodge twice, stop lending. Use a payment request in your app and be done.

Skip the dance. Send a short message with the amount and a date asking for the $60 by Friday. If they get weird about it, that tells you what you need to know.

Between daycare drop-off and emails, I text a clear reminder with the amount and a specific date. Keeps it neutral and quick. If they miss that date, I stop lending until they square it.

I overthought it forever, but a quick text worked.