Jonathan (Andrew McCarthy) and Skip (Rob Lowe) are roommates at an upscale prep school. Jonathan is from the country and is at the school by scholarship, while Skip is a privileged, handsome young man of the city. Skip decides that Jonathan needs some experience with the ways of the world, and sends him to pick up women at a bar in Chicago. While there Jonathan meets Ellen (Jacqueline Bisset), an attractive older woman, with whom he begins to have an affair. Eventually Ellen breaks off the relationship when she discovers that Jonathan is only 17. Things get even more complicated when Jonathan visits Skip's home over Christmas and discovers that Ellen is Skip's mom.