Hmmm. Given that Naoto is a bit of an over-achiever and possibly already taking classes at college, and Chloe is a recent HS grad who's taking the classic year off to save up for their first year in college, is it possible for them to have gotten to know each other through SAT prep courses?

AU Chloe, like her canon version, can be reasonably persistent with diffident ones, and is prone to teasing, maybe the sort to try and get a fellow student out there a bit more, even if it's just for coffee after a cram session.