Borrowing money from friends can be wildly uncomfortable. You want to keep it fun and friendly and polite, but at a certain point, you also might need your money back. If you sweep things under the rug and let them go by, you might end up resenting each other for unpaid debts or unbalanced books. This is why it’s important to be up-front and honest in the moment. If you need someone to pay you back, you should hit them with a Venmo request and keep reminding them about it until it’s paid. It might be slightly awkward to do, but it saves you a potentially ruined friendship down the line. 

This is way easier said than done, though. Money is an uncomfortable subject in this country, and everyone has different means. You also can’t assume someone’s financial status. Even if they seem like they’re doing okay, you never know what’s going on in their bank account.