S1 E11: "I feel cornered by a friend who keeps asking to borrow money."

Today's Question
How do I handle a friend whom I've lessened contact with because I'm afraid they'll ask me for money?

I let him borrow some when he moved into his new apartment and his roommate refused to actually pay rent or split utilities while my friend was crawling out of maxed credit cards. He paid me back but since then has asked more than once. I have 5 figures saved so I feel pressured to help out, but I want him to actually learn some lessons instead of coming to me for a loan.

And as a followup: how can I know what is financially expected as you get older? I'm self-employed (internet work with hard depression) but all my friends have adult jobs. Yet they also all still have student loans & credit card debt. I paid off my student loans, no credit card debt, have 25k saved and just bought a house thanks to my techie significant other. I still have a broke mentality since my significant other has 6 figures saved. It's hard to relate with my friends when there is such a mismatch of finances. We're all in our mid 20s.

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