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.
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.
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.
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.
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 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.
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.
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.
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.
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.