Steve Wilde (Will Arnett) is a filthy-rich, immature playboy trying desperately to win (or buy) the heart of his childhood sweetheart, Emmy Kadubic (Keri Russell), 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 (Will Arnett) plan to take Emmy (Keri Russell) and Puddle (Stefania Owen) on a family vacation is interrupted by the arrival of Emmy’s fiancé, Andy (guest star Cross), at the Wilde estate, who has his own plans for Steve.
To impress Emmy (Keri Russell), Steve (Will Arnett) vows to quit his job at Wilde Oil. Meanwhile, Puddle (Stefania Owen) gets some unusual help on her science fair project, and Fa’ad (Peter Serafinowicz) 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 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.
Wilde Oil caused a horrible spill, and Steve Sr. appoints Emmy head of the clean-up team. But it's a plot to get her out of his hair, and Steve finally figures it out and takes Emmy's side.