Fleishman Is in Trouble is not the kind of story that makes you want to start a family. The miniseries, a Hulu adaptation of Taffy Brodesser-Akner’s 2019 book of the same name, is ostensibly about a crotchety New York dad, Toby Fleishman (Jesse Eisenberg), and his divorce from his wife, Rachel (Claire Danes), narrated in the highly subjective voice of Toby’s journalist friend, Libby (Lizzy Caplan). But Fleishman unexpectedly evolves into a much more nuanced story about Libby and Rachel, exploring all the ways they chafe against where they’ve found themselves in middle age. As each experiences a midlife crisis driven by their mixed feelings on where motherhood has landed them, Fleishman becomes less of a divorce plot and more of a knotty portrait of two women at their wits’ end.
“If I had read my book while I was pregnant, I would have thrown it across the room,” Brodesser-Akner says. That did not stop Caplan, who welcomed her first baby shortly after she was cast, from doing everything she could to be involved with the series adaptation. As it turned out, the actor didn’t have to do too much finagling anyway. For Brodesser-Akner, who wrote and helmed the adaptation of her own book, Caplan was already at the top of her list to play Libby.
Between her college trip to Israel, her long tenure at an unnamed men’s magazine, and her reluctant move to the suburbs, Libby bears more than a striking resemblance to Brodesser-Akner, who, before she wrote the novel, spent years writing profiles at GQ and then the New York Times. “Libby is designed to seem a lot like me,” Brodesser-Akner says cagily, adding that she feels she’s put pieces of herself into all three of the story’s main players. Caplan feels a deep connection with Libby, too. “Everything about her felt so familiar to me that I trusted everything about who she was,” she says. But there was one crucial part of Libby’s narrative that Caplan couldn’t identify with: “I haven’t reached that suffocation point of motherhood … I’m sure I will eventually.”
What was casting the show like for each of you?
Lizzy Caplan: I wrote an email to one of the show’s producers, who also produced Masters of Sex. I said, “I love this. What do I have to do to be in this?” And that led to a Zoom with Taffy.
Taffy Brodesser-Akner: You were pregnant and wearing braids.
LC: I was very pregnant and very into wearing braids whilst pregnant. I know it wasn’t so seamless on their end, but on my end it felt pretty effortless.
TBA: My only heavy lifting was saying, “Do you think Lizzy would do this?” Anyone else would have been my second or third choice. Our producing partner started saying I was into witchcraft because I could summon things. I got everyone I wanted.
Taffy, did it ever feel like you were casting someone to play yourself?
TBA: Libby is designed to seem a lot like me, but I feel like all the characters are me. It’s like they’re ghosts of past and present. There are very few people in acting under 40 that seem extremely real to me, that seem like people who have more interest in expressing their vulnerability and their humanity than protecting themselves. I felt like Lizzy was a real person, and only a real person could play this role.
LC: I love to be called a real person. It’s true that you’re all of them. I don’t think you could write them so well if they weren’t all pieces of you.
TBA: People who know that I grew up with some financial instability, having seen episode three, understand that Rachel is even more like me.
LC: The birth scene in that episode, even though we’re supposed to feel a certain way about her at this point in the story, it still breaks through as something that’s gut punching.
What other factors went into the casting process?
TBA: It made sense to cast people that we think of as children, the way we think of ourselves as children. When we were first talking, you described the role as “grown-up.” It feels like everyone arrived here at this bewildering moment of Oh my God, it’s real. Time happened to all of us.
LC: Some actors have aged into this type of material, which is the stuff that made me want to be an actress. Just grown-ups talking about life. Adam Brody is a genius actor, and he should have aged into these really cerebral, cool parts, but there’s no material to support it.
TBA: When these scenes were going on and everyone was like, “Are you sure we should be just sitting here talking for eight minutes?,” I said, “Let’s just see if it works!” I had this confidence as if I’d done this before. But those scenes are my favorite. When these three friends are talking, you could just watch them forever. There’s great television out there, but I do hear this idea that a grown-up thing is hard to find these days. This is my contribution to the grown-up oeuvre.
What was filming like?
TBA: I thought there would be more of me explaining what I’m like. Turns out that’s what actors do. When you write, there’s a lot of negative space around the characters. The actors’ job is to build the things you didn’t write, and everything Lizzy built was specific and true and honest. We didn’t have to have a conversation like, “Listen, I know your kid is young now, but in 12 years, it’s gonna get a little ugly.”
LC: I hadn’t worked in a minute. My baby was 3-and-a-half months old when I started filming. I’d forgotten how to do this other side of myself, being an actress. I had some private meltdowns. But it never felt like I was supposed to be doing an impression of Taffy. Everything about Libby felt so familiar to me that I trusted everything about who she was. Even the parts I had not experienced or may never experience, if Libby felt that way in that situation, chances are I was gonna feel that way.
TBA: The only great decision I made was going in and saying, “I’m not gonna even pretend I know things.” At some point, Jesse explained to me that it’s not his job to be looking at the whole thing. It was my job to be looking at the whole thing and convey some kind of confidence that this would work out. I’ve only learned since doing these interviews that showrunners aren’t always there on set. I thought that was the job! But it must have also been a lot of pressure for you to have me there.
LC: I’ve been on shows where there isn’t somebody sitting there every day who knows the answers to all your questions. That’s a gift.
Were there any points of contention between the two of you?
LC: I started to get a little twisted up about narrating while also playing the scenes and being present in the moment. How is this person who’s so verbal, talking over everything that happens in the show, sitting in this scene and not being as verbal as she would normally be? Taffy had to tell me a bunch of times, “Don’t worry about it. It’s not gonna feel like you’re just sitting there.” I had to just trust Taffy. And she was right. So la di da.
TBA: The first time you brought it up was in the diner scene in episode one with the three of them. But you’re so present in that scene. You’re doing what journalists do, which is observing and reacting.
Fleishman paints a pretty complicated, and not always flattering, picture of motherhood and domesticity. Do either of you connect with that?
LC: The point that I’m on in the motherhood “journey” is so early and not, like, having bratty kids who are driving me crazy. I haven’t reached that point of motherhood, that suffocation point that I think is very universal and everyone experiences it at some point. Hopefully it’s just moments and not years. I don’t feel stuck in my role as a mother. I’m sure I will eventually.
TBA: When I was pregnant with my first child, I did not know how motherhood would change my life in terms of limiting my choices. If I had read my book while I was pregnant, I would have thrown it across the room and said, “This woman is broken. That will never happen to me.”
LC: I couldn’t stomach a version of parenthood that didn’t have the honest-conversation component. That feels very new. Taffy, when you had your kids, I’m sure it was a lot of, like, gauzy curtains floating in the breeze. Thank God the conversation is a lot more layered now. A lot of being a mother is a fucking drag. And I really like it! The fact that most people still can’t admit to that is very isolating for new mothers.
TBA: The Fleishman point of view on motherhood is that I can tell you my arm looks fat and I hate it and you never assume that means I want to cut it off. It is well established that mothers have a bond to their babies. Now let’s talk freely about the other things. You don’t need to say that Libby would do anything for her kids. She’s subverted her whole life. She’s wearing a tankini at a pool and serving grilled cheese. She’s allowed to have some questions. And some complaints.
LC: It’s one of the last stigmas in the arts. A mother who leaves her child is unforgivable.
TBA: A lot of people who read the book could not get over that. It was only men.
LC: I find that women are just as hard, though. Periodically, I look at baby message boards, and the guilt and the shame — it might as well be 1950. For a lot of people, motherhood is perfect, and if you say it’s anything other than perfect, there’s something wrong with you.
TBA: I’ve been away for a year and a half making this show. My family would FaceTime me on Friday nights over the kiddush wine, and wherever I was on set, everyone had to come look. I feel very guilty about that time — like it’s 1950.
Beyond understanding Libby as a character, did you find that you two personally had a lot in common with each other?
TBA: We both have a visibly Jewish urban upbringing. I would have been exactly like Lizzy, but when I was 12, my mother decided she was going to be extremely Orthodox. Lizzy, have you ever played a visibly, actually named Jewish character?
LC: Casey Klein from Party Down. “Klein” feels Jew…ish. I’ve gotten a lot of texts that they’re putting Fleishman Is in Trouble coffee-cup sleeves at bagel shops. Feels deliberate?
TBA: Lizzy is a lot cooler than I am. When I would talk about my misery in the suburbs, people would be like, “I don’t know, you kind of make sense in the suburbs.” Whereas if you try to stick Lizzy in the suburbs …
LC: The dirty little secret is I covet the suburbs. I liked how there were so many actual suburban friends of yours playing the extras in the show. I didn’t ask enough questions about that. We were skewering the suburbs. How did they take that?
TBA: They are the only people who are still my friends ’cause they accepted my misery not as a referendum on their choices. When you’re looking for authenticity, go straight for it.
LC: We went to a Seder at Taffy’s house for Passover, and all of your friends are exactly how I’d imagine the dream New York literati life. It feels so far from my own life. You, my friend, are too cool to be in the suburbs.