This is a really difficult one - I have a really close friend who I see or speak to several times a week. Without fail, the subject of money (and their lack of) comes up in conversation. Over the past year I've tried being sympathetic, offering practical solutions ie helping her sell some things, help her with her CV to get a part time job etc, plus DH has given them lots of free business and financial support but we're still in a position where she's crying on the phone to me for hours at a time because they can't afford the expensive dream house she's got her eye on and somehow feels entitled to (neither can we btw!).
I don't feel comfortable talking about our finances, and although I love shopping, am careful to keep anything I've bought to myself. DH has worked and studied very hard for years and finally got to a senior level in his profession. We are by no means rich - it's taken 10 years to reach this point and to begin with we were absolutely skint for a long time (before she knew us well). Her DH is highly skilled in his job but it just isn't that well paid a sector. I can sometimes feel her comparing our situations now and it makes me feel very uncomfortable.
I don't want to sound like a heartless person because I really hope I'm not, but it's really difficult to keep having the same conversation if she won't take steps to help herself. Basically she needs to get a job if she wants the lifestyle she aspires to and can't seem to see that money isn't the key to happiness. (One of my dc's has mild SN, for example, which gives me plenty to worry about.) I really want to stay friends with her but can feel my patience wearing thin. How can I get this across to her and preserve our friendship?