As summer turns to fall, Oscar seeks help from Garry, his therapist, and his ex-girlfriend Marilyn dreams of seeing her name "above the title." Peter questions his awkward existence with Brigitte as Sophie, now a "struggling single mother-to-be," hunts for the perfect apartment.
With Harriet's help, Oscars starts penning his blog as Marilyn seeks career advice from her talent agent, Larry Goldman. Aided by the Daily Gazette, Peter delivers Sophie the news she's been waiting for: a possible reason why Alessandro left her waiting at the altar.
Sophie encounters deja vu in her first support group meeting of the season as Brigitte meets her new movie star client Braeden Montgomery. Marilyn auditions for an off-off Broadway play about an empty room while Harriet wins a trip to the beach.
It seems everyone in Peter's life has forgotten his birthday... again. Oscar decides to apply for a job at Midgetville after flirting with Imogene, the bubbly bartender, while Sophie permanently moves into a client's empty apartment. Brigitte gets stuck at work with her flirtatious client Braeden Montgomery.
Peter gets scouted by a familiar face to join the cast of "The Scarlet Letter: Das Web Series." Sophie welcomes Harriet to her new apartment where they gossip over tea as Oscar trains at work with the one-eyed manager and Marilyn is unexpectedly swept off her feet by rapper Paris LeBlanc.
Marilyn, Brigitte, Sophie, Harriet, and Imogene seem to be living their own version of "Bonjour, Paris" from "The Battery's Down." Peter shoots his first day as Roger Chillingworth on the set of "The Scarlet Letter: Das Web Series," while Harriet, at the beach, finally meets Mr. Wright.
Sophie finally connects with her British crush, Dwayne Reed, at her final support group meeting. Oscar invites Imogene over for the first time as Harriet visits Marilyn and Audrey backstage. Peter and Brigitte escape group couples therapy, only to walk onto the set of Stark Star and Paris LeBlanc's new music video.
Oscar's overbearing mother unexpectedly visits him at work while Paris LeBlanc sends Marilyn some bad news in a rap video. Sophie and Dwayne Reed "break-up" on their first date as stylist Rhoda Rak and assistant Won leave NYC for Los Angeles.
Peter shoots the last day of "The Scarlet Letter: Das Web Series" as Sophie gets caught living in her former client's empty apartment. Oscar bumps into his ex-girlfriend Marilyn and finally gets to tell her what he's been wanting to say all season.
Sophie buys a one-way ticket to Europe as Harriet comes clean to her Mr. Wright. Peter stumbles upon Oscar and Imogene's new single before popping a question to Brigitte. After freaking out on Marilyn and abandoning Imogene, Oscar has one last emergency therapy session with Garry.
