Steve Wilde is a filthy-rich, immature playboy trying desperately to win (or buy) the heart of his childhood sweetheart, Emmy Kadubic, the über-liberal humanitarian who got away. Given the chance to reconnect with Emmy, Steve pulls out all the stops to win her heart.
Thinking their own lives are more difficult than each other's, Steve and Emmy walk in each other shoes, leaving Steve in charge of Puddle and Emmy socializing the night away to impress a powerful magazine editor.
Steve and Fa'ad are excited by the return of their college buddy Jack. Steve's concerned because Jack is such a party animal, and Emmy wants him to be more mature. But when Jack shows up, he's clean and sober now - and boring.
Emmy thinks Steve has abused his friendship with Migo, and sends Migo off to pursue his dream of painting. Steve, lost without Migo, decides to help Emmy with one of her causes, illegal immigration. But Steve accidentally supports the wrong side.
Mr. Lunt's worried that Emmy is secretly a gold-digger, and contrives to get Emmy and Steve to sign a pre-nup - even though Emmy has no intention of getting married. Steve and Fa'ad decide to help recent flood victims by opening a nightclub.