After an argument, Jerry breaks up with his disgruntled fiancée Avery (Kelly Preston). He then turns to Dorothy, becoming closer to her young son, Ray (Jonathan Lipnicki), and eventually starts a relationship with her. Dorothy contemplates moving to San Diego as she has a secure job offer there; however, she and Jerry agree to get married. Jerry concentrates all his efforts on Rod, now his only client, who turns out to be very difficult to satisfy ("Show me the money"). Over the next several months, the two direct harsh criticism towards each other with Rod claiming that Jerry is not trying hard enough to get him a contract while Jerry claims that Rod is not proving himself worthy of the money for which he asks; one point of contention is that Rod is not very likable and comes across as aloof to the fans. Rod takes Jerry's advice to prove he is worthy of his contract. Rod is playing well and his team is winning. Meanwhile, Jerry's marriage with Dorothy gradually deteriorates and they eventually separate.