Fiona hears from her stepfather, Garreth Pink, who has some interesting complaints about his new wife -- perhaps Fiona can turn him into an ally against her mother and get Web Therapy back up and running...?! Former assistant Jerome reports on his travels and the stipulations of baby Angus's trust fund. And Fiona takes on a new client, Maya Ganesh, a not-so-calm spiritual guru.
Fiona and Kip Wallice are rekindling their marriage, albeit solitary and separate from one another - definitely not a recipe for trouble... Garreth calls, having followed Fiona's advice with varying professional and familial results for Fiona and her mother, Putsy. Maya recaps Fiona's weekend at Gentle Circles and Jerome confirms Austen's penthouse "gift" is more burdensome than ever imagined.
Fiona takes on a new client, skittish, suspicious, lottery-winner Steve Olson, in hopes of solving her cash-flow issues. Fiona's neighbor and Jerome's promiscuous baby-mama, Gina, calls to complain about her boredom - she's already slept through all the construction workers at her house, so what else can she do?! Jerome is using and abusing Fiona's NYC penthouse to benefit baby Angus's education. And Fiona begins seeing a patient whose elderly girlfriend wants him to quit his unusual job!
Jeb Masters calls Fiona to complain about her behavior, since it's bordering on sexual harassment. Philadelphia neighbor, Grace Tiverton, is eager to strike up a friendship and will do absolutely anything to hang out with Dr. Wallice. Gina returns with examples of her new business venture, crediting Fiona's suggestion, and Steve Olson finally reveals that it's Fiona who should have trust issues.
Fiona discovers Grace is a little less politically connected than she assumed. Jerome admits he's no longer using the New York penthouse and can't justify paying Fiona's maintenance for her. Ewan Clarke, Austen's brother, calls to check in about the very specific terms of Angus's trust, and to determine if Austen's, well, sane! And Fiona's regular foil, Hayley, returns from Bali with some big news and an even bigger confession.
Construction next door at the Sokoloff-Feldman-Tate-Spinks residence is completely out of control, so Fiona retaliates, lobbing a grenade into Jerome and Hayley's relationship. Meanwhile, a desperate patient from the past breaks the rules and calls from witness protection, Ewan Clarke attempts to convince Fiona to declare his brother Austen insane, and Fiona's mother Putsy says she will do literally anything to influence the governor on Kip's behalf.
Jerome reports that Gina has embraced her carnal urges to an alarming degree, and needs Fiona to stage an intervention, and "Jacques" sees if Fiona can break "Betsy's" amnesia before it's too late. Nina Garcia offers Fiona an auction-won makeover that Fiona insists she doesn't need, and a new client calls to get some advice about her love life - luckily Fiona's an expert.
Kip discovers the real reason behind his law clerk's resignation. Nina Garcia recounts Fiona's disastrous makeover. Fiona discovers she has a fan in a very unexpected place, and Caspar Lee propositions Fiona for a strategic partnership.
NSA analyst Abel (DAX SHEPHARD) accuses Fiona of psychological terrorism, a pathological liar (MATTHEW PERRY) seeks help for his disorder, and mother Putsy reveals her grand completely illegal plans for Kip's future.
Season 4 ends with Kip's political plans being dashed by Fiona's scandal. Meanwhile, Jerome's involvement in Putsy's schemes puts him on the run; Gina returns from rehab a completely new woman; and Jenny lobs a grenade into Fiona's past.