All teenage Henry Krakow wants is to be junior lawyer to his father, whom he calls the Mayor. The Mayor is a shady, but successful New York insurance claims man whose next clients are the Xiaos. He brings Henry along to meet them, knowing the family has a teenage girl his age.

Henry falls in love with the daughter, Cassie, who closely watches over her elderly parents' dealings with the Mayor. Her father suffered an accident while fixing a roof and agrees to sign the documents the Mayor promises will compensate the family for the tragedy.

When they get home, Henry decides to bring all his allowance to Cassie because he knows his father's words are empty. Cassie convinces him to steal the documents from his father's office and bring them to her in exchange for a kiss. She's able to then alter the documents and give her parents a generous compensation.

The Mayor learns from his boss that the documents had been altered, but it was too late to withdraw the cash. He gives Henry a sad hug and tells him he needs to toughen up for the real world.

Later, when Henry returns to Cassie's apartment, he finds it completely cleared out except for a special pen that he'd given to her.