My concern is: ?what is your story really about? ?What is the primary story thread: the comeuppance of the Big Man on Campus (BMOC)? ?Or the rivalry between two schools? ?In either case, it's the same protagonist with almost identical events, but if the primary story line is the rivalry, then it seems to me that the rival for the girl friend should be someone from that story line -- from the rival school.
On the other foot, if the primary story line is about the comeuppance of ?the BMOC. then the rival for the girlfriend can come from either.
And to reiterate, I love the concept. And I hope the grand gesture arises out of who the nerd really is, not who he tries to be. ?
fwiw