When Keith's father discovers the college fund has been emptied, he is livid, but Keith ultimately convinces his father to respect his right to make his own decisions. He later uses his college fund, with Watts in tow, and selects a pair of earrings for Amanda. He is oblivious to Watts' attraction to him.
Watts tells him that she will appreciate a good kisser, and shows Keith how to kiss. With Watts' help, he sets out trying to plan the perfect date to prove he is worthy of Amanda. Watts enlists the help of another boy, trying to make Keith jealous, but he barely notices. Meanwhile, seeing her best friend with Amanda makes Watts realize her feelings for him are much deeper. Taking it as a chance to prove to Hardy that she does not need him, Amanda accepts. When Amanda breaks up with Hardy outside their school, Keith seizes the opportunity to ask her out. Unbeknownst to him, she has talked her way out of detention, and he is stuck with the school misfits, eventually making friends with troublemaker Duncan. Hearing that Amanda will be in detention, Keith gets himself in trouble in order to spend time with her. He treats Amanda as his "property" and is seen fooling around with another girl. She is dating Hardy Jenns ( Craig Sheffer), a self-absorbed boy from a wealthy neighborhood who thinks Keith is beneath him. Keith is enamored with Amanda Jones ( Lea Thompson), the most popular girl in school.
Keith's blue-collar father is obsessed with sending him to college for business, as he would be the first in their family to go. Blue-collar mechanic and aspiring artist Keith Nelson ( Eric Stoltz) and his tomboyish friend Watts ( Mary Stuart Masterson), who has been subjected to rumors that she is a lesbian, aspire to improve their social standing. The film is set against the strict social hierarchy of an American public high school in suburban LA.