Jack and Dylan begin a new life together, living aboard a yacht with Dylan's enormous trust fund at their disposal. On the surface everything seems perfect, but Jack has some dangerous enemies. So does Brandon, whose unpaid gambling debts lead to some frightening threats from his bookie. Meanwhile, Andrea and Jordan go on a date, Dylan and Kelly consummate their relationship, and Brenda and Donna take a self-defense class.

Brandon's out of control gambling debts are mounting up and his bookie, Duke, is getting impatient and wants $1,500 of losses paid up by the end of the week. He goes to extreme lengths to pay his bill by hiring another bookie to place bets, and his desperation leads to violence. Kelly feels that Dylan is slipping away from her, and her insecurity leads to an unhealthy obsession with her appearance. Meanwhile, David gets dumped by his label after his hack recording manager, Serge, has him record an out-of-tune song. Elsewhere, Andrea convinces a depressed Dylan to write a story about his experience with loss.