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 (David Cross) visits.
Steve tries to impress Emmy by vowing to quit his job at Wilde Oil; Puddle gets unexpected help with her science fair project; Fa'ad is locked in a vodka cellar.
Steve and Emmy try to reunite Puddle and her boyfriend when they break up right before the school's formal.
Steve tries to prove he can be less extravagant by throwing an environmentally friendly party.
Steve inadvertently throws an elaborate Renaissance fairy-tale wedding for Andy and Emmy.
Steve asks Emmy to a charity ball; Emmy tries to teach Steve that there is more to a woman than her appearance.
Thinking their own lives are more difficult than each other's, Steve and Emmy walk in each other's shoes.
Steve's stepmother (Drea de Matteo) tries to curb his excessive spending on the day Steve plans to finance Emmy's new nonprofit.
Steve becomes jealous when his former fraternity brother (Rob Corddry) charms Emmy during a visit to the mansion.
Emmy turns Migo into a local celebrity when she encourages him to follow his dreams.
Emmy agrees to sign a prenuptial agreement to prove to Mr. Lunt that she isn't only after Steve's money.
Steve's father shows up after he is forced into hiding after an oil spill.