Christina Applegate appears as Jenny Bologna, a "fixer" from Boston, who offers to do damage control for Fiona, and reveals a troubling secret that upends Fiona's world.
Dan Bucatinsky is back as Jerome Sokoloff, Fiona's former assistant, who now finds himself in charge of little Angus Clarke's enormous trust.
Tim Bagley is back as Fiona's ex-flame Richard Pratt, now Jacques Kamose. He and his wife Betsy, played by Julie Claire, are in witness protection, but they make contact when Betsy is asked to testify.
Jennifer Elise Cox returns as Gina Spinks, Fiona's former co-worker. Gina is now bored, living off her son's trust fund. She turns to Fiona for help in occupying her time.
Billy Crystal is back as Garreth Pink, a publicist who is starting to regret his decision to marry Fiona's mother Putsy.
Craig Ferguson appears as Ewan Clarke, the late Austen Clarke's brother, whom Fiona tries to manipulate into giving her control of baby Angus's fortune.
Jesse Tyler Ferguson is Steve Olson, a patient of Fiona's who has just won the lottery and is paranoid that everyone wants his money.
Calista Flockhart plays April Keating, Kip's new law clerk, who may have a devotion to her boss that goes beyond simple dedication.
Victor Garber continues as Kip Wallice, Fiona's husband. Kip's career is on the rise with a new Superior Court judgeship, but is he thankful to have Fiona on his arm?
Lauren Graham plays Grace Tiverton, Fiona's socially connected neighbor who will do anything to keep Fiona in her inner circle.
Jon Hamm plays New York voice actor Jeb Masters, a new client of Fiona's, who has a knack for making older women blush.
Allison Janney plays Judith Frick, the headmistress of an elite girls school in DC. She turns to Fiona for wedding night advice.
Rashida Jones returns as Hayley, the wife of Fiona's former assistant Jerome. Haley is back from an extended stay in Bali ready to mend fences with Fiona, but her act of goodwill forever tarnishes her husband.
Caspar Lee, YouTube sensation, appears as himself. He calls to revoke Fiona's auction-won makeover with Nina Garcia and offer her something else instead.
Gwyneth Paltrow makes a multi-episode appearance as Maya Ganesh, a spiritual guru with serious anger issues.
Matthew Perry is Tyler Bishop, a lawyer and pathological liar, who turns to Fiona for help.
Dax Shepard appears as Abel Jans, Fiona's biggest fan, who wants to finally experience the modality of Web Therapy for himself.
Lily Tomlin is back as Fiona's unpredictable Bostonian mother Putsy Hodge, whose competing online therapy business and best-selling book are a thorn in Fiona's side.