Before he was McDreamy , Patrick Dempsey was best known as Ronnie Miller, a socially challenged high school student who tries to buy his way into the popular crowd. When the opportunity presents itself, he pays cheerleader Cindy Mancini $1,000 to pretend to be his girlfriend for a month.
On their first day as a "couple," Cindy throws in a fabulous, five-minute makeover. She gels his hair, swaps his glasses for shades and rips the sleeves off his boring button-down. Dorky to dreamy in two seconds flat!