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.
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 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.
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 the overly obsessive Newell, but her handling of Robin has disastrous ramifications for Kip's campaign in the Season 2 finale. Later, Fiona discovers that her friend Austen may no longer be unattached; and Jerome and Haley have a surprise for the therapist.