I am VERY open to that idea. The path to get that to open sounds so freaking cute!

Yeah that could work! Smiles, waves, the occasional hello, he tries to change his route to see her a little more often before rescuing her stuff. I can imagine he might joke/tease that he is her body guard or purse saver or something like that afterward.

I think Al could help(somewhat), his daydreaming/people watching is usually to just escape reality. But I'm sure that can be molded into something creative(please do. I have been dying for some excuse to make him poetic)

A troubled reforming thief and a sick children's book writer. That sound's heartwarming already.