Having a Quarter-Life Crisis with Toby Fleishman
Seth Cohen and Janis Ian are shepherding me into middle age and I guess that's okay
When we were younger, characters on screen and their off-screen counterparts created a blueprint of the future for us. They showed us what it would be like to be teenagers, then what it would be like to be in college, and eventually become young adults. At the time, I wouldn't have guessed that one day, they'd lead me into middle age. Although maybe I should have.
I recently wrote about how watching The O.C. was like opening a time capsule of the early 2000s, and how Adam Brody’s character Seth Cohen helped welcome in a new kind of teenager in the media, and made Brody a staple of that era. When I finished the show and I couldn’t watch Seth proceed into adulthood, I did the next best thing: I watched Brody return to the small screen in an adult role. In Fleishman Is in Trouble, Brody plays another Seth, an old friend of the titular Toby Fleishman who Toby reconnects with amid a grueling divorce. Seth starts out as a classic bachelor — the one Toby goes to when he needs to replace his loneliness with a night out. While the two Seths are really different characters, to me, they existed side by side, a messy illustration of the passage of time.
I often use TV as a way to reminisce, to explore nostalgia through the lens of beloved shows, and to remember what it was like when my biggest concerns were whether or not I would ever be allowed to wear a tube top or smooch a boy. Rewatching the shows I first saw when I was a child or teenager puts me in touch with a past self, one who didn’t know what was in store for her, but could make predictions based on the lives she saw depicted on screen. It was much easier to catch glimpses of the future when there was so much of it stretched out in front of me. This becomes more difficult as you age and the artifice of television becomes more apparent. There are a lot more shows showing the ups and downs of even the mundane days of being a teenager or young adult than there are of being fully grown. But I occasionally find myself in the same position as I was in my family’s living room when I would watch reruns of Lizzie McGuire, wondering if too would one day impress my classmates and thwart my archnemesis with my ribbon twirling abilities. A show like Fleishman Is in Trouble once again allows me to look into the future. More specifically, it illustrates middle age — a time that is still far off for me, but inches closer with every wedding invitation I stick to my refrigerator with a magnet.
The show hit Hulu in 2022 and is based on the novel by journalist and author Taffy Brodesser-Akner. It tells the story of 41-year-old Toby Fleishman (played by Jesse Eisenberg), as he goes through a painful divorce and embarks on dating, reconnecting with old friends, raising his children and failing to take down a set of blinds in his new, downgraded apartment. When it first dropped, I didn’t watch. A show about two people in their forties whose marriage falls apart didn’t seem like something I could relate to. I was probably busy worrying about Jennifer Coolidge’s White Lotus character (and I was RIGHT to do so) and recovering from season eight of Bachelor in Paradise. I had no time to think about divorce, let alone the trials and tribulations of owning a brownstone.
But I was eventually lured in by the genius casting, which, in addition to Brody, is full of familiar names. While the storytelling and style alone would be enough to make me love this miniseries, the cast is what really makes it sing. Yes, they’re talented, but that’s not what made them perfect for this show. The creators filled the screen with faces we’ve watched grow up, who have iconic roles from their (and our) younger years. It’s hard to see Eisenberg without thinking of Adventureland, Zombieland and of course his portrayal of Aaron Sorkin's fanfic version of Mark Zuckerberg as a man with a semblance of rizz. Few people threw around as many iconic lines in one movie as Caplan did in Mean Girls; every time I see her, I hear her 22-year-old self shouting “your mom’s chest hair.” Danes burst on the scene in 1994 as the star of My So-Called Life and became a household name to most people in Baz Luhrmann’s Romeo + Juliet but became a household name to Rachel and I when she swiped Mary Louise Parker's husband Billy Crudup. Fleishman also features Josh Radnor, whose face will forever be associated with How I Met Your Mother.
While actors and actresses can often be associated with their former work, this casting feels somewhat unique. We’re watching the characters on screen figure out middle age after years of watching the real-life actors and actresses navigate their twenties and thirties. We’ve watched them wrestle with fame, dodge being pigeonholed by their famous early roles (to varying degrees of success) and now here they are: married, having children and settling into middle age. I’m not saying that I think Jesse Eisenberg in real life suffers from imagining his wife messing around with the guy she told him not to worry about like Toby, or that Adam Brody is out with the boys until sunrise because he’s afraid of his own loneliness, or that Lizzy Caplan is drowning in boredom in the suburbs — those traits are (hopefully) their characters’ alone. But the show’s entire plot hinges on aging, and it’s that much stronger because we’ve watched the cast leave childhood and solidify who they are despite the challenges thrown at them.
Watching entertainers we love and grew up with is top of mind in recent weeks, as people around the world mourn the death of Friends actor Matthew Perry. I have always been more of a Seinfeld or The Office girl if I must watch a sitcom, but thanks to my fiancé and his family’s love for the show, I’ve seen most of the episodes, laughed at Chandler Bing and even found myself at a Friends trivia. (One thing I hate is not being able to answer anything at a pop culture-themed trivia night, so I can promise you I did not have a good time.) Even though Friends was just in my periphery growing up, it was still a cultural staple of what it meant to be in your twenties at a time when I had no idea what being in your twenties meant. Being in my late twenties and watching a middle-aged Perry struggle with addiction and eventually die in a tragic way after years of seeing his youth captured on screen is crushing. It shows time is passing, but it’s also a reminder that when I was young, I looked at adult characters for insight into adulthood, like what it would be like to hang out with all my friends in a big loft in New York City and meet up for coffee at Central Perk. As a child, you don’t realize how much you romanticize the future — and the scary thing about looking into your future as an adult is you can’t be so easily fooled. Perry’s death is a reminder that Friends was a sanitized version of adulthood.
Perhaps it’s a stretch to compare the death of a beloved TV actor to a show about aging like Fleishman Is in Trouble, but the uneasiness in my gut when I learned of Perry’s death and when I watched the Fleishman crew tackle life was somewhat similar. Okay before anyone gets mad at me and starts screaming “40 is the new 30!” I am not saying looking down the road at middle age is the same as looking down the road at death. But it does mean struggling with being alive when you no longer have a blueprint.
TV is a way to see into another world, and when I was younger, I used it as a means to see into the future, to imagine a life that seemed far away but that would eventually be mine. As I gear up to enter my thirties, the future can’t hold the same shiny, exciting sheen as it could when I was younger — the stakes are higher, the responsibilities are becoming heavier. But Fleishman’s casting allowed me to enter the future without being terrifying by pumping the middle age story with nostalgia. Much of it is bleak. Without spoiling too much, I’ll say there’s a shift in point of view that forces us to reckon with the fact that the story Toby has shown us isn’t the whole truth. It’s his truth, and that means something. But the sudden change feels like a gut punch, reminding the viewer that no matter how strongly they feel they’ve been wronged or how carefully they’ve acted to ensure a future they want, the other people in the same situation may feel differently. The other people in our lives may have different plans, and we’ll constantly have to reconcile with that. The switch up centers Toby’s wife’s Rachel’s story, and shows that much of her behavior comes back to trauma from her first pregnancy. It’s one example of the show narrowing in on a fear that seems specific to the character, but is somewhat universal, at least to people who have thought about becoming pregnant. As a release, Rachel lets out a shattering, animalistic scream, and I felt it deep in my bones, a reminder of how much I fear that having children one day will mean losing control of my body.
But I felt like I finally had a blueprint for middle age and was being guided by characters I’d begun to trust in the same way teenage me watched shows to know what it was like to be in your twenties. Fleishman jumps through time, bringing us back to when the couple initially met in college, and when their difference in career aspirations hinted at trouble to come, and when they decided to have children, and when they decided to divorce. It forces Toby to ask: Did things go wrong here? Or here? Or here? It’s usually never one big event that causes a life plan to crumble — it’s a small decision, a slight disagreement, a twinge of jealousy that festers. While things like suburban life and motherhood seem so far for me now, Fleishman left signs for me to follow: Here’s everything to fear from an ordinary life. One day you may wake like Toby, and realize the perfectly crafted world you’ve molded for yourself is not all it’s cracked up to be.
But watching scary things play out on screen makes them feel less scary. And there’s hope in Fleishman, too. When television shows rip apart our sense of what a life should be, they tend to also put them back together — not always cleanly, but enough to move on.
“Nothing could make her unmake the choices that she made, she just didn’t know when she was making the choices that they were going to limit all the other choices that she could make in the future,” Caplan says in a tearful monologue during the last episode. She’s talking about Rachel, and she’s talking about herself, and she’s talking about you and me. “How can you live when you used to have unlimited choices and you don’t have them anymore?”
With this performance, Caplan is once again paving the way for me like she did when I was a kid. Her character is right: It feels like there are fewer possibilities in front of me than when I was watching Mean Girls for the first time. There are also fewer blueprints to follow in television and movies once you reach a certain age. But it’s in its wrestling with that fact that Fleishman brings me comfort. The middle-age characters don’t have life figured out, but I now know their 20- and 30-year-old counterparts didn’t either, despite what I thought as a kid. We’re all lost together, grappling with our shrinking pool of choices.
B Plot
Question: Whose the best TV villain?
Mallika: Okay stay with me… did anyone else watch Revenge with Emily VanCamp circa 2011? Why is the image of Madeleine Stowe as her mother-in-law in that putting the fear of god in me? It has been so long since I watched but I remember being genuinely terrified of that woman. It’s perhaps giving Lily van der Woodsen but without the redeeming qualities. Or maybe I am remembering wrong and she was also Mother with a capital M.
Oh, and Bob from Twin Peaks.
Rachel: There are probably a lot more iconic TV villains, but one of the most genuinely horrifying ones is David Tennant as Kilgrave in Jessica Jones. Like Revenge, that show also feels like a distant memory, one at the core of Kristen Ritter’s well-deserved peak (seriously where did she go?? Her guest appearance in Love & Death was not enough, my woman needs to star in some more prestige television pronto!), but the image of Tennant’s portrayal of a mind-controlling psychopath who haunts Jones’ PTSD fueled nightmares has stayed with me all this time. Kilgrave is rotten to the core and has tremendous control over any situation, frequently rendering our heroine powerless in a way that makes you squirm as an audience member. With Tennant (who as an actor has the uncanny ability to either thoroughly charm you or deeply unsettle you, matched only by Andrew Scott’s repertoire), the show captures a uniquely feminine fear, of someone taking over control, shattering the illusion of safety. I haven’t seen anything quite like it since if I’m being honest. In second place is Vecna from Stranger Things, which I just finished re-watching over the weekend. He wields a similar power that feels impossible to overcome.
C Plot
When we say we sometimes want to delete all of our social media, throw our phones in the trash Serena van der Woodsen style and live in the woods, we mean we want to be as off the grid as Winona Ryder walking into her first Netflix meeting about appearing in Stranger Things and asking, “What is Netflix? What is streaming? Is it like TV but different?” And our girl still got that check! It’s also apparently Stranger Things Day (aka the day baby Will Byers went missing and began a long journey of absolutely going through it at every turn) so Netflix is streaming the whole first episode on TikTok à la Mean Girls.
Carmy, Syd, Cousin and the gang are officially coming back for The Bear season three. Yes, Chef! Meanwhile, season three of Euphoria is not expected until 2025. HBO… babe… we fear we’ll be over it. How much bacon is Jacob Elordi going to have to eat to play Nate Jacobs as a full ass adult?
Alyson Hannigan did a little Buffy tribute on Dancing with the Stars. While we don’t condone people actually going on Dancing with the Stars, we do condone acknowledging your roots.
And finally, as Hunter Harris pointed out, hot girls can’t drive.