Friends and money never mix (did I just answer my own question?). I usually end up helping my friends move, drove one to a class for DUI, and have paid rent for a few when they were down and out, but when it comes to getting favors from them they can become really indignant, and attempting to collect money from anyone is always a pain in the ass.

It's not a necessarily a bad thing that it's making me withdraw from these people and people in general, choosing to only hang out with people for business related matters, which isn't a bad thing.

Wondering askTRPs take on when male friends continually overstep or attempt to overstep their bounds, especially when it comes to money.