Whilst Kip is at sexual reorientation camp, Fiona flies to New York to work on her book and meet with publisher Maxine DeMaine (Rosie O’Donnell). Whilst there Fiona talks to Kip's counselor Camilla Bowner (Meryl Streep), who decides Kip's recovery needs to take a drastic change.
When Fiona finds out what Camilla has really been doing with Kip's recovery, she decides she must act quickly to counter. Meanwhile, Fiona doesn't take it well when Maxine and Jerome re-write her book.
With Maxine no-longer a threat for her book; Fiona once again faces Robin, who blackmails Fiona into getting her a job on Kip's campaign. Meanwhile, Kip's campaign manger, Ben (Michael McDonald) finds out that Fiona's Web Therapy business isn't accredited and tells Fiona that she now has to suspend treating her patients.
In an attempt to get Web Therapy accredited, Fiona tasks her sister Shevaun (Julia Louis-Dreyfus) with signing the accreditation form. However, Shevaun decides that before she can sign the form, Fiona should first undergo the recommended 50-minutes sessions. Fiona tries to help a now unemployed Gina (Jennifer Elise Cox) find a job.
A reporter (Molly Shannon) starts interviewing Fiona, but instead puts an erotic story featuring Fiona on her blog; Newly sober television actress Allegra Favreau (Minnie Driver) wants to pitch Fiona's book for a Lifetime movie.
Fiona gets her first international client when Gemma Pankhurst-Jones (NATASHA BEDINGFIELD) calls from Buckingham Palace, where she works as a "proxy" for the royal family. When she says her recent marriage remains unconsummated, Fiona concludes this is therapy by proxy -- and the new royal marriage is in trouble! Fiona's conjugal advice is unsuccessful, Gemma's pregnant, and her husband is bound to know he can't be the father! Can Fiona save the British empire?
Gina needs a job, and Fiona helps to get her one in Alaska; Allegra prepares to play Fiona but insists that she fly to L.A. first, however, when Jerome asks an unwelcome Hailey to join Fiona, the whole trip turns into a disaster.
Jerome introduces his surrogate, Tammy (Selma Blair) to Fiona, where she learns that babies are expensive; Fiona finally sees the true extent of the relationship between Kip and Ben.
After doing a video chat with her former college classmate Newell Miller (David Schwimmer), Fiona receives a new client, Conan O'Brien, whom she's never heard of.
Fiona and Tammy discuss money but Tammy reveals a secret; While Fiona blackmail's Conan O'Brien, Fiona's mother (Lily Tomlin) calls for help, and Newell shows up at Fiona's house, uninvited.
Fiona's mother's crime is starting to worry her mother; Newell plans a romantic therapy session with Fiona to cure his illness. Meanwhile, Gina informs Fiona that Austen has promoted her, and Richard Pratt (Tim Bagley) starts dating Fiona's nemesis Robin.
Fiona cures Newell by setting him up with her sister, Shevaun, and Newell realizes that Shevaun is the one his obsession is coming from. Then, Fiona does a requested session with Robin and Richard, but things spiral out of control when Robin gets fired and the Campaign's fate is determined. Hailey (Rashida Jones) returns with Jerome, who are making a Whistling While I Worked broadway musical called Whistlin'. Kip then says he is going to Santa Fe, New Mexico with Ben, and Fiona is at long last able to be with Austen, however, a secret prevents it from happening.
Fiona finds the perfect client in Austen Clarke (ALAN CUMMING), the Scottish media mogul ? and he's every bit as delighted with her.
As luck would have it, Austen is perfectly situated to help Fiona with her latest venture, and she "reluctantly" agrees to let him put her on the map...
Fiona is flying high with Austen ? but an unexpected call from her husband could bring her right back to earth...