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.
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.
To impress Emmy, Steve vows to quit his job at Wilde Oil. Meanwhile, Puddle gets some unusual help on her science fair project, and Fa'ad gets 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 and Andy's rivalry for Emmy's affection reaches a breaking point leading to Steve inadvertently throwing an elaborate Renaissance fairy tale wedding for his adversary and the woman he loves.
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.