Seventeen years ago, when Lizzy Caplan was 24, it was foretold: she was going to be a star. Following the huge success of Mean Girls, in which she played the artsy outsider Janis, Caplan had been cast in CBS’s hottest new sitcom, The Class. At the helm were Friends co-creator David Crane and sitcom legend James Burrows as director. “This was the pilot to get, the show – it was going to be huge,” recalls Caplan, over Zoom from Los Angeles. Before the broadcast, the cast of eight were flown by private jet to Las Vegas, where they were treated to a lavish dinner and a night out at the casinos. “The whole purpose was for the creators to tell us, ‘This is the last time you’ll all be able to sit in a restaurant together without being mobbed,’” says Caplan. They had done the same thing with the cast of Friends. The Class was cancelled midway through its first season. But for Caplan, the early disappointment was instructive: “This idea of being teed up for this massive, life-changing thing that ultimately didn’t happen – I am the most grateful for learning those lessons.” Of course, Caplan has not done badly since. Having gained a cult following through Freaks and Geeks and Party Down, she made the leap from comedy to drama with Showtime’s critically acclaimed series Masters of Sex, in which she and Michael Sheen played pioneering sexuality researchers. Now Caplan is at the centre of “the discourse” in Hulu’s much talked-about miniseries Fleishman Is in Trouble, adapted from the novel by Taffy Brodesser-Akner. It stars Jesse Eisenberg as Toby Fleishman, a doctor going through an ugly divorce, and Claire Danes as his Waspy workaholic ex-wife Rachel. Caplan and Adam Brody play Toby’s school friends Libby and Seth, with whom he has recently reconnected in order to relive their shared past, and reckon with where it all went wrong. The show was well received by critics and has resonated widely for its depiction of midlife malaise. More than a month after its finale in the US, website the Cut recently reported, “the Fleishman effect” had sent New Yorkers into a spiral over their chronic self-comparison, postcode envy and choices in life thus far. Caplan welcomes the discussion – in her own life, too. “It’s been the greatest joy of this show – the amount of people who have reached out to me,” she says. “Based on these conversations that I’ve had with friends, it’s made a lot of us feel less alone in these thoughts.” Growing up in Los Angeles, Caplan had loved film and television shows that grappled “with adult questions”, like The Big Chill and the ABC drama Thirtysomething (one of Brodesser-Akner’s inspirations). “It was the type of material that made me want to be an actress – and to be a grownup,” she says. But over the past 15 years, as the indie movie industry has shrunk, such true-to-life stories have been scarce on the big screen. “That makes me sad on many levels,” Caplan says, “because I think they’re the types of things that actors really want to be doing.” Fleishman, she says, “feels like it’s made up for all of this lost time, all the years when I couldn’t find anything.” Though, on paper, Libby is the most settled of her friends, with a good marriage, thriving kids, financial stability and a community, she can’t help looking critically on her life: how did she go from an ambitious young journalist in New York, to a fortysomething suburban mom? Now 40 herself, Caplan got married (to British actor Tom Riley) in 2017 and had their first child Alfie in 2021. This she credits with sparing her the brunt of Libby’s discontent: “I have been married for only five years; I had my first child 16 months ago … No part of me feels like I’ve been cast off to the suburbs.” Nonetheless, Caplan says of Libby: “I identified with her more than any other character I ever played.” Their similarities were even “a bit eerie”: they are both Jewish, took “that Israel trip” as teenagers, and remained close with friends from that time. Then there are their shared circumstances as working mothers. Alfie was three-and-a-half months old when Caplan was shooting Fleishman. “Obviously I think most women of this age can identify with trying to figure out where they fit in their professional worlds,” she says. “Even though I didn’t feel stifled, I can fully identify – as I think we all can – with mourning the loss of youth.” For all its relatability, Fleishman also surprisingly radical for exploring that restlessness in a woman, especially without a romantic object. There is nothing really wrong with Libby’s life, yet she struggles to feel part of it. “She had lost so much of what made her herself,” says Caplan. Divorce is never touted as the solution, and though she and Toby are close, neither of them mistake their mutual dissatisfaction for desire: another way in which her melancholy rings true, says Caplan. “So many of my closest friends are men, and there’s never been even a whiff of romantic entanglement. We’re conditioned as audiences to expect that, but it doesn’t really reflect real life.” Instead, through Libby, the show depicts the quietly simmering side of the discontent that, over eight episodes, we come to understand dramatically came to a head for Rachel Fleishman, ending her marriage. “We’re used to seeing men’s stories; we can handle the more subtle version of a man’s midlife crisis – the Libby version – but when we see a woman’s midlife crisis, it usually resembles Rachel Fleishman’s: the big, huge, explosion,” says Caplan. “The idea that you could fit both into one story so effectively is just another thing that impresses me about Taffy.” Brodesser-Akner adapted her own novel as a first-time screenwriter, with the dramatic reveal of the final act brought into heart-rending relief by Danes as Rachel. She and Libby spend most of the series as satellites in Toby Fleishman’s orbit, in service of his story – until they are finally brought together, in those emotional final episodes, and find common ground. Though very different and not natural friends, Fleishman’s two female leads together embody something about the daily struggle of modern women, even those who are privileged – and especially those who worked and parented through the pandemic. Now exhausted audiences might identify as “a Libby” or “a Rachel” in the way that, in simpler times, they did Carrie or Charlotte, or Monica or Phoebe. “I love the female friendship in this series, even though we barely see it. I like to think that they stay in touch,” says Caplan. But Libby’s new understanding of Rachel is also subtly devastating because of her realisation that the men in their lives seem unable or unwilling to share in it. “There’s a very unique version of heartbreak when your friends disappoint you,” agrees Caplan. When she was young, she, like Libby, defined herself as a “guy’s girl”. “That felt like a superpower, and I look back now and it was the opposite. Your superpower is your relationship with other women.” But it can take time to realise, Caplan says. “Especially if your profession is more of a man’s world, it feels like you’re sidestepping the patriarchy if you’re one of the boys.” There’s that rueful laugh again. “But that’s just not it, unfortunately.” Set in the lead-up to Trump’s election, Fleishman makes a sharp critique of the palatable, placating approach to feminism that has only been exposed as more toothless in the years since. Caplan herself pushed for the script to include Libby’s quip that, as T-shirt slogans go, “The future is female” is as meaningful as “Free beer tomorrow”. “It’s such a heartbreaking truth: you wouldn’t be allowed to say that in front of all the boys if it were true … We’re all buying the T-shirt, which is placating us, and not actually solving the problem.” But the trouble in which the Fleishmans have found themselves is not simply a battle of the sexes, or even a failed marriage or post-divorce struggle. What distinguishes the series is Brodesser-Akner’s journalistic attention to balance – and her compassionate view on our very human failings. All the characters “are a mess”, says Caplan. “They’re all projecting their own stuff on to each other the entire time, even though I think they believe they are helping each other.” Indeed, friendship emerges as a lifelong lifeline. “These relationships couldn’t be more important in their lives, and I feel that way: I’m married, and I have a child and my friendships are right beneath that,” she says with emphasis. “It’s how we survive.” As for Caplan, she seems to have only relatively recently struck the jackpot of balance and reward – personally and professionally. She loves motherhood, she says, and has started writing her own projects with Riley; one, a film, is currently in development. “I just feel a sense of calm that eluded me for my entire youth. In retrospect, I’m very happy I never had to experience that shot-out-of-the-cannon, life-changes-overnight thing … but again,” Caplan adds wryly, “this is how it feels looking back.” Fleishman Is in Trouble is on Disney+ on Wednesday