Business is booming for reasons that have nothing to do with Fiona's actual abilities, but she's not complaining until she gets a new client with a personal connection to her family.

Fiona's marriage crumbles when she discovers her husband's secret life, while her mother's hidden past threatens Fiona's business plan.

Kip's ex-girlfriend has a business proposition for him and Fiona, but the details must be ironed out by their overworked campaign manager.

Fiona's old friend Newell tries to spark a romance with her; and she and Conan O'Brien square off against each other. Meanwhile, Fiona's mother looks to have lost her grip on reality again.

Newell is still bent out of shape over an experience he and Fiona shared in college 20 years ago; and Putsy gets caught up in a legal entanglement. Later, a disappointed Fiona learns that an old flame may finally be over her.

Fiona cures Newell of his obsession, but her handling of Robin has disastrous consequences for Kip's campaign; Fiona is surprised to find that Austen isn't flying solo anymore.