How to Ask Someone to Pay You Back (Without It Being Awkward)

You lent someone money. They haven't paid you back. Here's how to handle it with practical scripts you can actually use.

Why Asking Feels So Uncomfortable

Asking for money back is emotionally loaded. But here's the thing: you were generous enough to lend money when someone needed it. Asking for it back is the natural conclusion of the transaction.

The Core Principle: Be Direct, Be Kind, Be Factual

Direct: don't hint. Kind: assume good intentions. Factual: reference the specific amount and date. This combination works because it's honest without being aggressive.

5 Scripts You Can Use Today

From the casual check-in to the final follow-up, five ready-to-use messages for every situation -- including a digital nudge using DebtTracker's shareable reminder link.