He used to be more masculine... but now he seems more feminine. He doesn't have many male friends... he never tries to impress anyone.
I know what I want in a guy, and it's hard to realize that some of those things will never manifest in him. There was only one other I've ever met that had everything in that sense, but he's long gone now.
The only way I think he'll come around is if he finds a new group of friends and gets some confidence... and finds a way to thrive, physically and mentally. Seems like that will never happen...