Here’s an update: 10 days ago, I called my friend to follow up on my email offering to help by paying for a service (movers, a medical bill, etc). She declined and asked if I could get her a prepay Visa card or if I could add her to my bank card. I really feel that was overstepping her boundaries and I declined. Today, she sent me a request asking for $2000. At this point, I don’t feel like helping at all as I feel she wants the money to pay her credit cards and that’s not how I want to help her. She has about $70,000 worth of credit card debt and until she changes her spending habits, I don’t see that changing in the future. I would rather help with one time expenses or not help at all as I’m not going to enable her spending. I’m pretty sure I am right, but feel a little guilty for sticking with my boundaries.