He hasn't been my boss in three years - so that's what I'd say is the difference - our relationship was very professional when he was my boss. Before either of us knew I was bipolar, I met up with him at a professional conference in denver (about 6-9 months after I'd stopped working for him) and he asked me if I wanted to smoke marijuana with him - signaling a dramatic departure from how it was when I worked for him. I think he knows better now, but that's what I mean by things being complicated.

I work on coping skills that I can engage instead of emailing him, but I'm not perfect. And I'll never really be able to separate how much he feels sorry for me for bipolar vs how much he sees me as a former protege (academia is complicated) vs how much is a sort of friendship.