My pedantry for the day - anyone can "go to" Harvard. Being enrolled as a student there is a different story. I'm sure Ben has physically been on campus at some point so perhaps the question should be changed accordingly.
My pedantry for the day: when you say someone "went to" Harvard, it is more or less universally understood that what you mean is that they were enrolled as a student there. Not that they visited the food court.
The question "Has dated multiple women named Jennifer" is not a great question, because we don't (and won't) have a definitive list of everyone either actor has dated.
You simply can't make the claim that Matt Damon has never dated a Jennifer, or two.
You could further restrict it: fellow celebrities named Jennifer, or something like that.
The dating lives of celebrities, being an object of grotesque obsession for so many, are pretty thoroughly studied and documented. The names of every woman Matt has dated or been rumored to have dated since 1988 are Skylar, Claire (Danes), Minnie (Driver), Winona (Ryder), Kara, Penélope (Cruz), Odessa, Rhona (Mitra), and Luciana (his wife since 2005). No Jennifers.
You make a good point, so perhaps it's more a technicality, but I still think the question would be improved by qualifying it as "publicly" or "known to have".
Loved Deep Impact however...
Somehow I got 9/15, including the least guessed answer/
You simply can't make the claim that Matt Damon has never dated a Jennifer, or two.
You could further restrict it: fellow celebrities named Jennifer, or something like that.