No, I wouldn't say my buddy has intentionally picked out women who bring drama and craziness, Galagirl. I think he has been attracted to emotional women who tend to open up to him a lot, quickly, and perhaps people like that tend to be on the loony side. I'm like that myself and I think that is why we are such good friends, except I'm not loony (I hope). He also has historically been attracted to women who pay him a lot of attention and are willing to spend a lot of time on the relationship, right off the bat, so that would encompass people who tend to get obsessive and spooky. Does that make sense?
You make a good case for not actively pursuing a friendship with her. He can't avoid her completely since they have a couple of social circles in common, and I don't think he wants to do that, but he can at least steer clear of hanging out with her in a situation where she could cross his boundaries.
Thanks for your input, and for yours too, YouAreHere.
Female, married just about forever to Scout. My boyfriends are E. and C. Both are married, and C also has another lover, J.