Asking someone to pay you back is a tricky dance. I really don’t have a problem with Venmo requesting exactly how much someone owes me, but a lot of people aren’t that financially confrontational. It’s very common to have a «You get me this time, I’ll get you next time» dynamic, and that’s all well and good if you stick to your word, but a lot of people don’t. There have been countless stories about people who lie about money problems to avoid paying. On the other side of the coin, there are young people who Venmo request their friends for food, only for it to be revealed that they used their dad’s credit card to buy it and are pocketing their friend’s money. It’s easy for dishonest people to brush off these discrepancies in expenses as «not a big deal» because they aren’t 4+ figure discrepancies, but that doesn’t make that true.