In the Season 2 premiere, Fiona's friend and financial backer, Austen, suggests she send Kip to a camp for sexual reorientation, allowing budding author Fiona to go to New York and meet with Austen's publishing executive. Later, Fiona hears from Kip's counselor, who has some radical suggestions for Kip's recovery.

Kip's counseling is having an impact on his life, which isn't boding well for Fiona; Fiona's editor and Jerome do a rewrite on her book, totally excising the author's friend and backer, Austen.

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 endures a real therapy session with a Boston psychiatrist with whom she has a disturbing history. Meanwhile, a former coworker on a job hunt spends more time dishing about Fiona than she does trying to impress her prospective employers.

Fiona's interview with a freelance journalist gives the campaign some needed exposure. Meanwhile, a reality star wants to turn Fiona's book into a TV-movie.

A frustrated Fiona seeks Austen's help in dealing with Kip, his campaign and reality-TV star Allegra.

Fiona meets the surrogate who is carrying Jerome's triplets and discovers that this is going to be an expensive proposition. She also learns that Kip has a more-special relationship with his campaign manager than she imagined.

An old college friend rings up Fiona with a peculiar problem, while a phone call from Conan O'Brien comes with some unsolicited advice.

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.