Fiona must undergo real 50-minute therapy with a psychiatrist in Boston whose longtime history with Fiona throws up some disturbing roadblocks for both of them. Meanwhile, former co-worker Gina is trying to find work.

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.

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

Frustrated with Kip, his campaign, and with reality TV star Allegra, Fiona turns to her publishing magnate Austen for help, but finds she must handle her creative differences on her own

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 and Austen send Kip off to sexual reorientation camp while she flies to New York to work on her book. There, she hears from Kip s counselor, Camilla Bowner, who suggests a drastic change to jump-start Kip s recovery.

Fiona is interviewed by freelance journalist and part-time blogger Kirsten Noble, and the resulting publicity gets a lot of attention.

Fiona faces her husband's ex-girlfriend, who has a business proposition for them.