Probably not how he meant it, and upon reflection he probably just meant that he wished she could have been the (seemingly) low-stress, pop-culture fan that so many girls her age are today instead of the fugitive she was, but I think to a lot of people his remarks came off as:
"Hey, this girl was cool and all, and I'ma let the tour finish, but hopefully she'd have been my fan 'cause I'm the greatest boy wonder of all time."