Tim Bagley continues as Fiona's former co-worker and ex-flame Richard Pratt. This season, Richard is hired by Fiona's husband's political campaign and falls in love with Fiona all over again.
Selma Blair plays Tammy Hines, a surrogate hired by Jerome and his wife to carry their triplets, who arouses Fiona's suspicions when she asks for more money.
Dan Bucatinsky continues as Jerome Sokoloff, Fiona's assistant and ghostwriter, who clashes with Fiona when he shows unsettling signs of independence.
Julie Claire continues as Robin Griner, Kip Wallice's manipulative former girlfriend, whose actions force Fiona to hire her to work on Kip's campaign.
Alan Cumming plays Scottish billionaire media magnate Austen Clarke, a new patient of Fiona's who quickly falls under her spell — much to Fiona's romantic and professional benefit.
Minnie Driver plays Allegra Favreau, a B-movie actress and newly sober reality star who options Fiona's memoir for a TV-movie starring herself.
Victor Garber continues as Kip Wallice, Fiona's husband, a Philadelphia lawyer whose political ambitions — and unconventional sexual life — challenge Fiona's marriage and career.
Michael McDonald plays Ben Tomlund, Kip's campaign manager, whose deep and increasingly personal friendship with Kip — along with his desire to control Fiona for the good of the campaign — makes Fiona his enemy.
Conan O'Brien appears as himself, and contacts Fiona for help with a serious problem: he can't seem to express his anger at his sidekick, who often appears funnier than his boss.
Rosie O'Donnell plays Maxine DeMaine, Austen's second-in-command, who is forced to edit Fiona's unpublishable book, most of which grossly offends her spiritual principles.
David Schwimmer plays Newell Miller, the son of Fiona's college professor. Newell witnessed a romantic encounter between his father and Fiona, an event that's haunted him ever since. He's contacting Fiona on the advice of his new therapist to find closure, but Fiona has other ideas.
Molly Shannon is Kirsten Noble, a journalist and blogger whose postings on Fiona cause political problems for her husband -- but an uptick in business for Fiona.
Meryl Streep plays Camilla Bowner, a consultant brought in by Kip's political handlers to help reorient Kip's sexuality with her extremely hands-on approach.
Lily Tomlin continues as Fiona's unpredictable Bostonian mother Putsy Hodge, whose residence in a psychiatric rehab facility has unintended consequences.