I've always tried to flesh out alternate routes. I had the moms route which I don't think anyone was really interested in; the Heather Kaminski route was deliberately a subversion of where that was going; and of course the Shelly Nolan and Mariah Alloway routes (the latter as part of a game).
And I think there's a lot to be said for 'average' girls. Will can be a wolf in sheep's clothing - although that argument is weak given that no one is looking for a wolf, so you'd need to set up conflict. There's also something to be said for 'average' girls, or even less desirable, if it's deliberately moving to a specific aim. The problem is that Will generally takes a long time to get even close to that.
But in terms of alternate routes... I still have no idea why Will Goes to Hollywood has never been viable, or Will Takes Over Saratoga Falls never happens, either. If you could be anyone, why the hell would you be in high school?
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