Keith Nelson (Eric Stoltz), an artsy high school outcast, tries to land a date with popular girl Amanda Jones (Lea Thompson) with some help from his tomboy best friend, Watts (Mary Stuart Masterson). However, his advances draw the ire of Amanda's snobby ex-boyfriend, Hardy Jenns (Craig Sheffer), who makes plans to get even. Matters are further complicated when Watts realizes she likes Keith as more than just a friend and tries to convince him to stop pursuing Amanda.