This isn’t your parents’ midlife crisis. The stars of “Fleishman Is in Trouble,” an adaptation of the 2019 novel by prolific profile writer Taffy Brodesser-Akner, aren’t exactly what you think of when you hear “middle-aged.” But that’s kind of the point — they don’t believe they’ll become middle-aged until they’re already in it, as it sneaks up on you. This series also sneaks up on you. You don’t realize there’s all that much to it until you’re a number of episodes in.
It starts out mildly enjoyable and completely familiar, as we’re introduced to Toby Fleishman (Jesse Eisenberg) dodging nosy questions about his recent divorce from fellow affluent Upper East Side parents. The tropes about pilates-doing moms, ultra-competitive private preschools, miserable husbands, and “Boss Bitch” t-shirts are bountiful and unsubtle. At the beginning, Toby doesn’t have the most civil relationship with his ex Rachel (Claire Danes), who we barely see in the pilot. All we know is that she’s a successful and very busy theater agent who’s also a “total bitch,” according to Toby’s friend Libby (Lizzy Caplan), the narrator of the series.
On top of all the marks against Rachel, she’s a pretty awful co-parent. Toby is furious when Rachel drops off their two kids (Maxim Jasper Swinton and Meara Mahoney Gross) with him a day earlier than scheduled, with no warning and no explanation, which is apparently out of character but not completely shocking behavior. What does shock Toby is that she doesn’t respond to any communication all day. She’s ghosted all of them.
Here’s What’s New on Hulu in November 2022
Toby is not being ghosted, however, by the female population of New York. In the earliest days of his separation from Rachel, while he’s still reeling from having to move from an Upper East Side “palace” to a “hovel” of a bachelor pad north of East 90th Street (in television tradition, the “hovel” is of course, anything but), one of his adoring young medical residents (Ava Yaghmaie) introduces him to the world of dating apps. To Toby’s great surprise and delight, he’s become a desirable commodity since the last time he was on the market. As a successful hepatologist “who gives a shit,” he can’t keep up with the endless parade of sexy women who are willing to throw themselves at him — we’re left to assume Rachel isn’t having the same experience.
As part of getting his groove back, Toby reconnects with his old friends he hasn’t seen since his single days, Libby and Seth (Adam Brody). Libby becomes more of a focus and the series’ best character as it progresses as she, a housewife to a burnt-out lawyer husband (Josh Radnor) and disaffected former magazine writer, realizes how much she envies Toby’s freedom and seemingly endless options as a single man.
The series plays with chronology by zooming back in time to the evolution and dissolution of the Fleishman marriage. Older millennials and younger Gen X-ers, the primary audience, will get a particular kick out of seeing Eisenberg, Kaplan, and Brody playing younger versions of themselves and looking just like their most iconic adolescent characters: Mark Zuckerberg from “The Social Network,” Janis Ian from “Mean Girls,” and Seth Cohen from “The O.C.”
We can’t say much more about the series without major spoilers, but just keep in mind that there’s more to Rachel than the materialistic shrew Toby makes her out to be, and the insights into male sexuality from a woman’s point of view turn out to be trenchant if not exactly new. With “Fleishman Is in Trouble,” Taffy Brodesser Akner proves to be just as talented at writing TV as she is at writing novels and viral magazine profiles.