The problem is that if I went with the "I am in" approach, and followed MWD's books, I would encourage the flirting, joking, spending time together stuff. And try to build on that...
But we all know my boy Dan has some issues with a capital I...
All the hanging out in the world won't fix that. And he has said basically point blank he doesn't want a relationship with anyone, he is depressed, hates his life, doesn't feel safe opening up, yadayadayada...so I would consider being his gal pal a cheeseless tunnel leading only to 'expectations' and 'disappointment' on my end, and 'cake' on his end.
So actually, boundaries and tough love/firm stance is the best bet, I think.
p.s. Anybody know a cute fun guy within an day's drive of Omaha?