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

Fiona must act quickly and boldly to counter the inroads Camilla Bowner is making on her life with Kip. Her once-promising friendship with Austen Clarke is threatened when Maxine and Jerome rewrite her book Austen's nowhere to be found.

With her book safe from Maxine's editing pencil, Fiona faces Kip's ex-girlfriend, who's got a proposition which must be handled by campaign manager Ben, who's got his hands full with the candidate's wife and her unlicensed Web Therapy...

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 frustrations with Kip make media magnate Austen Clarke even more invaluable, and she asks for his help with troublesome journalist Kirsten Noble. But Fiona has to handle her own "creative differences" with reality star Allegra.

Jerome introduces Fiona to the surrogate who is carrying his triplets. Meanwhile, her relationship with her husband's campaign manager suffers when she discovers the extent of HIS relationship with Kip.

Fiona gets a call from a voice from her past, and another from what she hopes will be her future when Conan O'Brien seeks her help and offers some of his own.

Fiona uncovers some surprising news about Jerome's surrogate, Conan O'Brien flexes his muscle long-distance, and Newell Miller does his best to get up close and personal. Oh, and Mother is insane - again.

Fiona's mother is in trouble with the law, and Newell Miller has a bone to pick with Fiona over a shared college experience twenty years ago... Meanwhile, Fiona's old flame Richard has healed his broken heart, much to Fiona's dismay.

Fiona cures Newell of his obsession, but her handling of Robin has disastrous consequences for Kip's campaign. Fiona's surprised paramour Austen no longer flies solo, and Jerome and Hayley have a plan to freshen up Fiona's world.