I just reread my post from early August, and almost 4 months later, my dating life looks similar.
Jack and I stopped seeing each other even as friends. Something incredibly banal and boring happened --- fill in your favorite Brady Bunch episode subplot minor minor conflict. After nine months of impeccable communication skills learned in MBA school, he blamed and accused, sent endless emails, ending with "what else short of slapping you would show you that I was upset." The whole situation surprised me. I just didn't write back, and that was it.
New romantic interest seemed extremely promising: we connected well (most recent date 6 1/2 hours of just talking), he's smart with BA from a top-20 small liberal arts college, taught high school math at a prep school, and he is well-built and good-looking. It didn't even bother me that he was a starving artist and estranged from his surviving parent after the other parent's protracted illness. Until it turned out that in the recent past, around when I was finishing grad school, he was homeless for several months. Homeless as in all of his belongings in a bag next to a park bench that he slept on because he ran out of friends to stay with, as he lost his friendships after staying with each of his friends.
Why do I have such an affinity with the troubled?
He didn't go into more detail about his time being homeless, but yesterday I saw homeless men standing with signs by the road off the highway yesterday asking for food (I gave one the apple that was supposed to be my afternoon snack), and I started thinking about the myriad degradations of homelessness and the wall of dehumanization between the homeless and non-homeless ("everyone else"), and it breaks my heart that he had to endure all of this.
I feel of two minds about this.
On the realistic hand, obviously an enormous red flag. The specifics do not matter. He has less of a buffer to protect him than most people, having chosen to go to art school instead of continuing in his steady job, a complicated family, and a tendency towards depression, but whatever the reasons, someone who could actually fall so far once could do so again. And he still does not have a steady income: a few jobs that are a part-time job with low enough salary that he still qualifies for some types of public assistance.
On the optimistic hand, he also pulled himself up from such a hole that is so deep most of us cannot imagine it, and he is wise enough to know that he cannot get into a real relationship until he feels more steady on his feet. He is also wise enough to avoid tangling relationships with social work. And I feel like I connect better with him than 90% of the men I've met this year.
On the realistic hand, I can hear so many women saying the same thing, and just ending up burned.
Other prospects are two men a long plane ride away: George (who does like me, it turns out) and the wedding guy (who now calls me a couple times a week, and is slightly disappointed when I get off after 2 hours, and he is looking for another job in closer cities).
Oh, and a just-minted-PhD from school whose personality I find really attractive and I think he's cute, but he is very fat. Now that he's defended, we have time to get to know each other. The thing that puts me off from him has nothing to do with him, just the social context. He's one of those "really nice guys" that "someone should date" but no one around him wants to. When people saw me with him once, they got all excited, and somehow it makes me uneasy to be that "someone." [Addendum 1/8/10, it turns out that the excited woman who saw us told her roommate that I was having brown bag lunch at school with this guy, who told the Starving Artist, and presumably others.] But with all considered, there's a great deal to be said for stability.