Dear Steve and Shirley, I need some help with one of my closest friends. He and I have known each other since middle school and he’s always been a bit lazy. He comes from a fairly privileged background and I believe that made him feel entitled to certain things in life, without actually working for them. We are in our early 30s now and he still lives with mother, works part time, and never finished college. The majority of his time and money is spent doing photo shoots for Instagram, because he seems to be trying to brand himself as a socialite or local celebrity......

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