The teen drama A Night in the Life of Jimmy Reardon is directed by William Richert, who adapted the screenplay from his own semi-autobiographical novel Aren't You Even Going to Kiss Me Goodbye? Set in a wealthy Chicago suburb during the 1960s, middle-class Jimmy Reardon (River Phoenix) hangs out with his upper-class best friend, Fred Roberts (Matthew Perry), and sleeps with Fred's snobby girlfriend, Denise Hunter (Ione Skye). He spends his time writing poetry and drinking coffee while he decides what to do after high school. His parents won't help him pay for tuition unless he attends the same business college as his father did, but Jimmy doesn't want to follow that path. Instead, he focuses on coming up with enough money for a plane ticket to go to Hawaii with his wealthy yet chaste girlfriend, Lisa Bentwright (Meredith Salenger). On the night of a big party, Jimmy is given the task of driving home his mother's divorced friend, Joyce Fickett (Ann Magnuson), who conveniently seduces him. Since he is late picking up Lisa, she goes to the dance with the rich Matthew Hollander (Jason Court) instead. Jimmy then crashes the family car and shares an intimate rapprochement with his father (Paul Koslo).