One of those glamorous people with too much money and too much time on his hands, Zach (Lukas Haas) looks like he's living the Hollywood dream. There's a steady stream of beautiful women coming in and out of his posh mansion in the hills, and every night he makes his way through the hottest nightspots for a party that never ends. A divorcée with a five-year-old son, Zach has become a master at seducing women without ever getting too close. But all that's about to change - he's met a girl he calls "Crazy Eyes" (Madeline Zima, "Californication"), and she’s not like anyone he’s ever met before. Flirty but withholding, intelligent but damaged, she’s the one woman Zach can't have, so naturally he wants her above all others.
While Zach's hard-partying lifestyle - aided and abetted by his bartender pal Dan (Jake Busey) - threatens to go off the rails, family concerns begin to play a major role in Zach's life. While his ex-wife becomes more financially demanding, Zach grows closer to their son, finding stability and maturity in his role as a father that's absent from the rest of his life. And as Zach begins to embrace fatherhood, his own father (Ray Wise) becomes seriously ill - which in turn leads to Zach's mother (Valerie Mahaffey) having a mental breakdown. Will the quest for love and the responsibilities of family life help this poor little rich boy become a man?