I am in a similar situation. My boyfriend has had several different jobs over the past 5 years. He was jobless for several months on and off. With each job, it seems his income just remains the same or drops. But, unlike your friend, my boyfriend is very socially friendly and upbeat on the surface. He has no problem interacting with anyone. I don't understand why he doesn't have a well establiahed career by now. He is 45 years old. I struggle with this because I have worked in the same field for 20 years and make fairly good money, own a home, etc. while he struggles to pay basic bills. I don't understand it and I don't have any answers, but I can relate to the situation.