Filthy-rich, immature playboy Steve Wilde tries to win the heart of his childhood sweetheart, a liberal humanitarian.

Steve plans to take Emmy and Puddle on a family vacation; Emmy's fiance visits.

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 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 leading to Steve inadvertently throwing an elaborate Renaissance fairy tale wedding for his adversary and the woman he loves.

When Steve invites Emmy to a charity ball, she is determined to prove to him that there is more to a woman than her physical appearance.

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's randy stepmom arrives at Wilde Mansion to curb Steve's excessive spending - on the day Steve plans to announce he is bankrolling Emmy's new non-profit.

Steve's excitement turns to jealousy when a former fraternity brother arrives at the mansion and charms Emmy.

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.

Steve's dad visits in the wake of an oil spill and gets Emmy to spearhead cleanup efforts, but Steve is suspicious of his father's true motives.