The series starts with the character that Brodesser-Akner’s arguably biggest influence, Philip Roth, would relate to most. Eisenberg’s Toby, a liver specialist in New York City, has just hit a strange point in his life: he’s divorced from his wife of 15 years, Rachel (Claire Danes), and finally seeing himself as a hot commodity thanks to dating apps. He’s having a lot of sex. A whole world of opportunity has been opened for him, or so it seems, as he chases the rush of getting a hot stranger from your phone to want you. That high only lasts so long when he is stuck taking care of his two young kids, Solly and Hannah, after theater agent and hard-working ex-wife Rachel suddenly drops the kids off in his apartment early one morning and ghosts everyone. She seemingly drops off the face of the earth, no calls to her assistant answered.
There is a lot of initial angst in this story toward Rachel, especially as Toby looks back on a relationship that began with love and corroded with passive-aggressive disagreements about practically everything. Rachel is missing, but she haunts this story, and making its reflections about their clashes about money, status, and his considerably more attentive parenting all the more gutting. In a Roth narrative, this might all play out differently, or its anger toward women might feel a certain kind of way. But part of the power of “Fleishman is in Trouble,” as a series but also a true page-turner, is how this is a Trojan horse to a greater understanding about the women in Toby’s life.
We learn about Toby’s life initially from the off-screen presence of Libby (Lizzy Caplan) whose voice hits us from the beginning. Libby has known Toby since a trip abroad in college (along with the suave and directionless Seth [Adam Brody]), but they have been out of touch for years, until Toby reaches out to find a friend. She’s also faced her own big changes in life, having moved to the New Jersey suburbs and become a stay-at-home mom, leaving behind a previous version of herself that worked in a magazine, prowled New York City art house movie theaters, and had more independence. Like Rachel, Libby orbits around other moms whose lives seem to revolve around their status and offspring. And like Rachel, Libby does not have a #MomSoHard preciousness for this life role. (Libby’s awesome vintage t-shirt collection is its own rebellion against the catch-phrase shirts about brunch, wine, etc. that populate this series’ costuming for modern motherhood.)