Oh, I know this feeling all too well. A close friend once ran a small agency and owed me for a few months of freelance work. The friendship made everything feel ten times heavier - you don't want to be the one pushing, but you also did the bloody work.
A few things I learned the hard way:
No contract doesn't automatically mean you're stuffed. Any written proof - invoices, messages, even a casual "yeah I'll sort it next week" over text - counts as evidence. Start building that paper trail now if you haven't already.
Send a professional, emotionless email summarising what's owed, the dates you worked, and when payment was originally expected. Keep it clean. That email becomes a record.
Give an actual deadline. Not a polite hint. "I need this settled by [date]" changes the conversation fast. It forces a decision.
If they keep stalling, look into small claims court in your country. Being outside the US adds complications if they're based there, but it's not a dead end depending on where you are.
The honest truth: if someone genuinely wants to pay you, they pay you. Months of delays usually mean cash flow problems on their side, not a scheduling issue. Treat it as a business problem, not a friendship problem - because they already have.