My Awesome/Awful Popularity Plan by Seth Rudetsky
Justin has two goals for sophomore year: to date Chuck, the hottest boy in school, and to become the king of Cool U, the table in the cafeteria where the "in" crowd sits.
Unfortunately, he has the wrong look (short, plump, Brillo-pad curls), he has the wrong interests (Broadway, chorus violin), and he has the wrong friends (Spencer, into Eastern religions, and Mary Ann, who doesn't shave her armpits). And Chuck? Well, he's not gay; he's dating Becky, a girl in chorus with whom Justin is friendly.
But Justin is determined.
In detention one day (because he saw Chuck get it first), Justin comes up with a perfect plan: to allow Becky to continue dating Chuck, whom Becky's dad hates. They will pretend that Becky is dating Justin, whom Becky's dad loves. And when Becky and Justin go out on a fake date, Chuck will meet up with them for a real date with Becky. Chuck's bound to find Justin irresistable, right? What could go wrong?
My thanks to Barbara for letting me know about this title. Add your review of "My Awesome/Awful Popularity Plan" in comments!