This week’s episode of Web Therapy features talk show host Chelsea Handler as Fiona Wallice’s ex-husband Chris. They met in college when Chris was still a man, but he recently underwent gender reassignment surgery to avoid sinning when having sex with men. Now, Chris is married to a man who has no idea she used to be a man. She’s called to reconnect and experience some of the old college glory days again - but conversation soon dissolves into petty competition and backhanded compliments. Since Fiona and Chris got a divorce, Chris had been paying Fiona alimony eventually amounting to a quarter of a million dollars, even though Fiona remarried and had remarried and been married for 18 years. Chris tells Fiona she owes her that money now because alimony is supposed to stop after the person receiving it gets married. As Chris was telling Fiona this, Fiona’s Internet miraculously starts “cutting out” and Fiona hangs up.
Fiona’s next call is with Nick, the gang member who is obsessed with playing online poker. He’s an incredible player but last week was beaten really bad by a player with the handle “F in Philly.” During today’s call, Fiona lets the details of that game slip, revealing to Nick that she was “F in Philly,” the player he’s vowed to kill. Instead, when he finds out Fiona is the player, he’s even more interested in joining forces with her to crush other people online and win more money. Fiona isn’t interested in helping, but Nick insists and tells her instead that he is going to abduct her and force her to play poker with him. Just after Nick threatens her, he’s taken from his desk by force by interventionists. Fiona counts herself lucky and starts another game of online poker.
After the online poker, Fiona receives a call from her mother, Putsy. She’s on Fiona’s boyfriend Austen’s jet. Fiona’s mother had stolen her idea for therapy over the Internet and created a new company called Net Therapy. She then sold it to a company out of the UK, Omnimedia, which it turns out is owned by Fiona’s boyfriend, Austen Clarke. Putsy went to London to receive the final payment for the transaction. She starts telling Fiona about how Austen’s baby with Gina is due any day now, and that he’s really looking forward to it, though she tells him not to get too excited because parenthood wasn’t the best experience for her by far. Putsy is heading to Boston on Austen’s jet to deliver a eulogy at her deceased roommate’s memorial. In memory of where they met doing puppet theater at an asylum, Putsy has decided to use socks in a “socko drama” eulogy. Putsy called in the first place to speak with Kip even though she is aware that Fiona and Kip haven’t spoken to each other in a long time.
Fiona’s next call is with Sylvie, who feels much better about her situation since the last time they spoke. Apparently Fiona inspired Sylvie to contact Kraft about mocktails, a powdered drink that Fiona offered to showcase on her show to her clients for Sylvie in exchange for a cut of the money. Kraft loved Sylvie’s idea to bring the mocktail powdered drink to the digital space, so they offered her a job. She’s decided to “play the game of life” and once she receives some of the benefits from her current job, she’s going to quit and take the job at Kraft. She’s also decided to bring the guy she was stalking the previous week along with her to Kraft. Sylvie wants to hire him then turn around and fire him the next week to really break him because of what he did to her. Fiona insists on getting a cut of Sylvie’s new business venture, but Sylvie threatens to report her to the Psychological Review Board for malpractice.
Chris calls Fiona again - not asking for money - but instead for therapeutic help. Chris divulges to Fiona that she’s been having an affair. Her husband went through her desk and found a folder marked “My First Marriage,” where there are pictures of both Fiona and Chris when she was a man. She’s told her husband that those pictures are of Chris and Kip, telling him that she was married to Kip. So, Chris’ husband believes that she’s now in an affair with Kip. Chris wants to set up a dinner between the two couples to prove to her husband that she’s not having an affair with Kip, but that would be kind of hard for Fiona considering the state of their divorce. Fiona suggests sending Chris video evidence of Kip’s gay relationship to prove Chris is not having an affair with Kip. They share an awkward, condescending goodbye and hang up.
Fiona’s final call is with Austen while he’s at the hospital. It’s the day after Austin married Gina and Fiona and Kip spent the night together. Fiona tries to continue the conversation - but Austen is too busy with her wife’s labor to give Fiona more time.
New episodes of Web Therapy air Tuesdays at 11pm/10c on Showtime.