Full disclosure, I'm a huge Bosstones fan. I've known Dicky Barrett since I was a kid. Not only did I start going to Bosstones shows about 5 years before MTV figured out who they were (surprisingly easy to sneak in to the Kenmore square clubs as a teenager), but he's a friend of the family (a couple of my aunts and uncles who are only 12 -14 years older than I am used to hang with him.. never got the story if one of them was actually dating or not), and I went to school with a couple of his cousins.
Yes, Massachusetts really can be that small a place... at least when you've got as big a family as I do.