Roberta his best bet ???
I dunno, after life spent in the office and board rooms, I think he could do a lot worse than hanging out with Roberta and getting in touch with his inner 'hippie'. I think he could tame her controlling personality at least to the point of being tolerable.
She seemed to be a nurturing type but at the same time someone who is strong enough to call him out on his BS and help him become more self sufficient.
I could also see this leading to a morphing into an RP McMurphy type within a year or so ...