CAST & CHARACTERS
KIP WALLICE (Victor Garber)
Fiona's long-suffering husband Kip is also her attorney. Kip is successful and comfortable, and he is bitterly resentful of the money Fiona spends on herself, and on her new business. Their relationship is cordial at best, and they clearly have intimacy issues, as Kip would rather have soup than sex.
RICHARD PRATT (Tim Bagley)
Fiona's former co-worker, Richard becomes one of Fiona's early Web Therapy patients. But Fiona and Richard have a backstory. There was a sexual incident between them at their workplace which they both have widely varying recollections of, and the spectre of the incident continues to rear it's head during Richard's sessions.
GINA SPINKS (Jennifer Elise Cox)
Gina is the ditsy receptionist at Fiona's former workplace. Fiona turns to Gina for inside information after she approaches her former employers to invest in Web Therapy, and ends up learning some ugly truths about what they really thought of her.
JEROME SOKOLOFF (Dan Bucatinsky)
Jerome is a patient of Fiona's from the old fifty-minute session days. Fiona admits to him openly that his sessions seemed like "self-indulgent blather" to her and she is hopeful that he will now be able to get to the point. Insecure and easily manipulated, Jerome becomes Fiona's great hope for the success of Web Therapy when he reveals he has potential incest issues.
HAYLEY FELDMAN-TATE (Rashida Jones)
Jerome's girlfriend Haley agrees to participate in Jerome's Web Therapy sessions, but it's clear she has bigger issues with the relationship than the fact that she and Jerome might be related.
KAMAL PRAKASH (Maulik Pancholy)
Kamal is an IT worker from Kip's office whom Fiona recruits to help her set up her internet system. He becomes uncomfortable with the arrangement when Fiona believes that he is making sexual innuendos towards her.
PUTSY HODGE (Lily Tomlin)
Putsy is Fiona's proper, upper crust mother who is having money troubles. Namely, she's giving all of her money away, and not to Fiona. Putsy is openly judgmental and hostile towards Fiona. She thinks Web Therapy is a ridiculous waste of time and an embarrassment, and she lets Fiona know it in no uncertain terms.
TED MITCHELL (Bob Balaban)
Hired by one of Fiona's potential investors to evaluate her, Ted is initially very skeptical of Web Therapy, but Fiona perseveres and achieves some surprising results.
CLAIRE DUDEK (Jane Lynch)
Claire is a high profile marketing executive who reluctantly comes to Fiona for therapy to deal with her anger management issues. Fiona is anxious to have Claire represent Web Therapy, and an outrageous game of cat and mouse ensues.
JUSTIN FEIN (Drew Sherman)
Justin and his girlfriend Bryn come to Fiona for couples counseling. Justin is resentful that Bryn spends too much time working and thinking about work. Fiona sympathizes with Bryn, at least until she finds out what Bryn does for a living.
BRYN (Patty Guggenheim)
Bryn and her boyfriend Justin sign up for couples counseling with Fiona. They are having issues around Bryn's job, which Justin thinks takes up too much of her energy. Fiona initially sides with Bryn, until she finds out what Bryn does for a living.
ROBIN GRINER (Julie Claire)
Robin is a mysterious new patient of Fiona's who thinks a lot of herself and her appearance. Fiona tries to call her on it, and ends up learning that they share something very personal in common.