Chicago, 1962. Jimmy (River Phoenix) is a confident Casanova who loses his college money to a female con who takes it for a supposed abortion. He attempts to borrow money from his best friend Fred ("Friends" favorite Matthew Perry) but this doesn’t work out. Jimmy’s father will pay for his tuition if he stays home and goes to his alma mater, which Jimmy doesn’t want to do. Jimmy then goes to visit his girlfriend Lisa (Meredith), a rich girl who is attracted to the danger and charm of this boy from "the other side of the tracks". To Jimmy she is a challenge; the one girl who won’t give herself to him. He talks to her about his dream to just pack up and move to Hawaii. Lisa is unable to give Jimmy any money. Jimmy also tries, to no avail, to borrow money from Fred’s girlfriend Denise (Ione Skye) who Jimmy has a weekly tryst with. After finally getting money from a wealthy elder woman, Jimmy has sex with a friend of his mother’s named Joyce (Ann Magnuson) and is two hours late for his formal date with Lisa. Lisa has since gone to a dance with another guy and, when Jimmy finally finds her, she confesses this was the night she was going to give herself to him. But she knows he must have been with another woman and breaks up with him. Lisa leaves the dance with her date. Jimmy follows and is beat up by her date. After wrecking his car, Jimmy learns his father is having an affair with Joyce and, realizing his father is not who he thinks he is, makes a connection with him. He decides to try to attend his father’s alma mater.

This film is well written and nicely put together although it is not one of River Phoenix’s better performances. Meredith, however, shines in her role as the beautiful, rich virgin, Lisa Bentwright.

The first shots of Meredith are of her playing tennis in a cute tennis outfit. Her first scenes with Jimmy show she likes to be playful with him and kiss but will not let him touch her sexually, which drives him nuts. She shows the character cares for Jimmy (when they talk about his future plans) and that she is thrilled by his danger and self-confidence. The good girl who likes the "bad" boy.

Meredith has some great moments. Lisa’s curiosity and innocence are well played when she asks to see Jimmy’s penis ("Is it always hot like this?…..Does it like me?…"). She has some brilliantly acted scenes toward the end of the film at the dance during which she is looking very glamorous in a formal gown and poofed-out hair. Her sadness when she breaks up with him is deeply painful and full of hurt. And her confession to him that she wanted him on this, their last night together (she had great plans for them and was going to make it a night to remember) is filled with longing and sadness. Meredith does a wonderful job of portraying the girl every boy dreams of having as a girlfriend. Even Jimmy Reardon.