Does anyone else have a friend like this?

He’s on depression meds and has seen a psychologist in the past. Doesn’t help him though.

This is a tough situation.

There may be no answer, or it might take a lifetime to find it. I assume considering your avatar you have spoken to him about higher powers. He will be in my prayers.

Thinking pragmatically, (I don't recall if you said the age of his parents), some type of conservatorship might be in order for when they have passed.
 
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I learned a long time ago that you cant save the world or someone that doesn't want to save there selves, IMHO you need to cut this guy loose so he is not taking up so much space in your head and move on. I have had to cut several old school friends loose but it usually involved drugs or alcohol use that they wouldn't let go, I don't need those kind of people coming up the driveway especially when my grandkids are around.
 
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I have a cousin that's similar — late 40's and still lives with her parents. She did go to college, but quit because of something that 'wasn't fair' like they wanted her to do the same work as everyone else.

As others have said, you have to have an enabler in this situation, her parents. She has two siblings that lead a normal life, live in other states, work, etc. Her parents allow her to live it home and do nothing, so that's what she's doing.

When I was 20, I was going to community college and working. Though not really trying very hard at college. My parents told me that I can stay for up to a year, but I was going to start paying rent. Rent would go up $50 per month until I was gone. I found a place in under 2 months. One of the best things that has happened to me in life was moving out. I fought with my dad all the time. I started getting along with him great after moving out.

Some people just need a kick in the ass.

There's a line in the Pink Floyd song 'Time' that comes to mind: No-one told you when to run. You missed the starting gun!
 
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