There are certainly legitimate reasons to feel bad for him. The man trudges through Tinseltown as a square-jawed specter, the guy an audience might not order, but will tolerate. Yet, he’s still so talented that you can’t look away: Gone Baby Gone was impressive. The Town was the clearance bin version of The Departed (he even included an embarrassingly obvious cranberry juice reference to make it absolutely clear), but it was bearable. And every guy I’ve ever gone out with lives and dies by Good Will Hunting. Speaking of: Ben is one half of a bromance that predates the word, albeit the lesser half. He’s Matt Damon’s best friend, sure, but sometimes he seems more like Matt Damon’s shadow. This makes me sad, because I think he has more to offer.I do suspect that everything I feel for him comes from personal anxiety. First, a fear that who you are to others, and who you are to yourself, can really be so disjointed, as he claimed in a 2009 Esquire profile . And second, this hyper-focus on being taken seriously. Pop culture doesn’t like our women hungry for success, or wounded in its absence. We bristle at Anna Kendrick and Anne Hathaway because they’re so obviously performative; we cut the vaginas out of strong women, and make memes out of the sad ones. So maybe I’m watching Ben because he's open with a sadness and dissatisfaction that women are rarely allowed to feel so publicly.