Filthy-rich, immature playboy Steve Wilde tries to win the heart of his childhood sweetheart, a liberal humanitarian.
Steve’s plan to take Emmy and Puddle on a family vacation is interrupted by the arrival of Emmy’s fiancé, Andy, at the Wilde estate, who has his own plans for Steve.
Steve tries to impress Emmy by vowing to quit his job at Wilde Oil; Puddle get unexpected help with her science fair project; Fa'ad is locked in a vodka cellar.
When Puddle’s boyfriend breaks up with her right before the school’s fall formal, Steve and Emmy each decide to try to reunite the kids with disastrous results
Steve sets out to prove to Emmy he can be less extravagant by throwing an environmentally friendly soiree.
Steve and Andy's rivalry for Emmy's affection reaches a breaking point.
Steve asks Emmy to a charity ball; Emmy tries to teach Steve that there is more to a woman than her appearance.
Steve and Emmy want to see whose life is more challenging, so they switch places: Steve looks after Puddle and Emmy tries to impress a magazine editor.
Steve gets a visit from his stepmother, who wants to rein in his spending. But her timing isn't good since Steve is about to finance a new nonprofit for Emmy.
Steve's fraternity brother visits and charms Emmy, much to Steve's chagrin.
Emmy gets Migo involved when she champions immigrant rights, and this tests Migo's loyalty to Steve as Migo is thrown into the limelight of fame.
Though Emmy isn't interested in becoming Steve's wife, she signs a prenup to prove she's not after his money. This then fulfills an engagement clause for Steve, which triggers a financial windfall for him.