Doomed youth: the genius of ‘Fleishman is in trouble’

It’s not just Jesse Eisenberg’s character who’s in trouble. Perhaps we all are—pining for yesterday, letting today pass by
April 5, 2023

Lots of shows are well cast, but not many can claim to have achieved some kind of genius in casting. Fleishman is in Trouble can. It’s the TV adaptation of Taffy Brodesser-Akner’s hit 2019 novel of the same name, now on Disney+ in the UK. It follows Toby Fleishman, recently divorced and played with perfect neurotic charm by Jesse Eisenberg, as he tries to negotiate the disappearance of his ex-wife, Rachel, which has left him juggling their two young children and his job as a doctor. The story is narrated by Toby’s college friend Libby, with whom he reconnects after his marriage breaks down, who is going through a slower burn crisis in her own marriage. It’s Gone Girl meets Scenes from a Marriage by way of a Nora Ephron-esque, wry, New York-Jewish sensibility.

Right from the start, you feel uneasy. Clare Danes, who plays Rachel, appeared in My So-Called Life as a teenager and became known to UK audiences as the lead in Baz Luhrmann’s Romeo + Juliet, opposite Leonardo DiCaprio, in 1996. Libby is played by Lizzy Caplan, whose breakout role was as the teenaged Janis in Mean Girls from 2004. Libby and Toby have a college friend, Seth, a part that went to Adam Brody, who played another Seth on The OC between 2003 and 2007. Eisenberg is best known for roles from 10 years ago. There are more: almost everyone in the show provokes a double take. These people are in their middle age? Can the actor who played Ted Mosby on How I Met Your Mother really be almost 50 now?! 

It situates you where the characters are: aware of, and uncomfortable with, the fact that we’re all getting old. There are many ideas the show conveys well: the hideous banality of divorce; the sting of unfulfilled ambition and professional envy; the laugh-one-minute-cry-the-next absurdity of dating. But it’s the presentation of ageing that’s stayed with me the most. 

In flashback scenes of the characters’ early twenties, when they were living in Jerusalem and had the world laid out before them, the actors are shot in shimmering soft focus. In the present, a rather sharper focus is placed on the fact that these once bright young things made choices that have locked them into life paths they weren’t totally aware of choosing. Libby wishes she hadn’t quit working. Rachel is battling burnout. Seth has noticed all the other party boys at his firm are a decade younger than him. And Toby has been spat out into singledom at a time when he expected to have settled comfortably into middle age. 

In the first few episodes, things look pretty much par for the course: divorced guy finds out about dating apps, hates his ex-wife, and fumbles being a single dad. There is also the alienating fact that the world the Fleishmans move in is insanely rarefied: the upper echelons of moneyed New York. It would have been all too easy for the show to have us sneer at these characters. Sometimes, it’s true, their privilege is a little exasperating. 

But the ageing stuff builds beautifully as the series goes on. By the final episode, when Libby’s story comes most fully to the fore, you’ve all but forgotten Toby’s Tinder troubles and angst about homeownership in the Hamptons.

Libby describes to Toby a book she wants to write, about a recently divorced man whose wife dumps the kids on him and doesn’t appear to be coming back. “How are you gonna write it, there’s no ending, it has no ending yet?” he asks her. “I don’t know, maybe this is the ending,” she replies, gesturing around at the engagement party they’re attending, an event that more obviously suggests a beginning. Rather than offer neat conclusions, Fleishman suggests that life isn’t shaped much like a story. 

The last note of the show emphasises the point. “What were you gonna do with the fact that you couldn’t win this fight?” Libby asks in voiceover. “That was the problem. You were not ever going to be young again. You were only at risk of not remembering that this was as good as it would get, in every single moment. That you are, right now, as young as you’ll ever be again.”

Then she says, “And now,” perhaps 20 times, as scenes flash up from Libby’s early marriage, late marriage, college years. “And now. And now. And now.” It’s devastating.

You don’t have to be in your forties, or married, to find Fleishman an affecting lament for lost youth. Maybe it’s come at the right time for everybody, post-pandemic: a show about waking up suddenly and finding that a chunk of your life has passed by, almost without you noticing.