The quest for the most Bill Simmons story in history is a long and arduous one. With that in mind, I want to be cautious here, but it is possible that after all these years, we have a winner.
The Sports Guy’s appearance on the latest Rewatchables podcast from The Ringer yielded this nugget: Simmons dumped his girlfriend after seeing Good Will Hunting in the theater and realizing he didn’t have the same passion as Sean Maguire, played by Robin Williams.
More specifically, he wouldn’t have given up Red Sox World Series tickets to “go see about a girl.”
Here’s Simmons (16:00 mark):
“I saw the movie that winter and I was dating this girl who lived in Chicago who, in my columns, was the original Sports Gal. She had moved to Chicago so we were dating long distance. I had gone to Chicago twice — I really liked her — I had gone to Chicago twice, I was freezing cold, I had no money whatsoever, the plane tickets were like $350, and it was just expensive and she was making more money than me. I was like, I don’t know how this can work, I don’t know how this can work with her in Chicago. I saw this movie and I saw the “I’m going to go see about a girl scene” and I had, like, this life moment. I was like, would I do that for this girl? And I was like, I wouldn’t, I don’t want to leave Boston, I feel like something good is happening here. I can’t leave. I wouldn’t go see about a girl. We broke up like within a week because of this movie.”
Probably a rough listen for Simmons’ former flame, if she’s a subscriber. To her I’d only say: “It’s not your fault. It’s not your fault. It’s not your fault.”