Whatever It Takes (2000)

High school senior Ryan Woodman and every other male student at Gilmore High has a massive crush on the most luscious knockout ever to walk its hallowed halls, Ashley Grant. The only problem? Ryan is persona non grata in the popular set and hardly worthy of Ashley's attention. Enter Chris, resident babe magnet, who's pining to no avail after Ryan's best friend Maggie, a girl with beauty, brains and a big heart. It's four weeks until graduation, and the clock is ticking for Ryan and Chris to snag their respective dreamgirls. Chris and Ryan, flanked by bumbling buddies Floyd, Cosmo and Dunleavy, go to outrageous lengths as they hatch a plan which, if successful, will land them both with the right girl- or so they think.