Everett goes ring shopping with Eve planning to propose to Isabel. Isabel is forced to break up with him but agrees to still attend the wedding together.
Everett finds Leo at the Lukens home. Jennifer passes Leo off as her poet boyfriend Dean. Then Dean shows up. Karen meets Doug. Isabel runs into Leo's dad looking to go see the Dodgers. It's a lot of wrong assumptions and first meetings.
First, Leo offers Isabel a crate and then he asks her to move in. Jennifer is angry and her parents are worried. She assumes that Doug is moving out. Jake falls for Jennifer.
Leo's father plans to move out of town leaving Jake's future uncertain. Isabel gets a painting job from her father for Leo despite the reluctance of both men.
Isabel's father bonds with Jake over computer golf and hires him as an intern. Jennifer wants a party for her 21st birthday. Leo is concerned that Jake is spending time with the Lukens. Jake is out with Jennifer and wrecks the Lukens' car.
Leo is worried about Jake. Isabel's cousin Anne Pryce arrives to look at colleges. Isabel is tired of getting stuck with the uptight violinist and her dad pays Jake to drive Anne. The two young people find a connection.
Karen stalks Doug at the car lot. She has a fling with him and Leo has suspicions. Jennifer gets a love letter from her professor Schrader. Isabel reconnects with Everett and his dog.
Isabel has moved back with her parents and cut her hair short. Karen is living with Doug after leaving Alan. There is awkwardness between her and Leo. Leo's grandpa has a heart attack. Jennifer is sleeping with her married professor.