A few years ago I watched a movie with Miles Teller and Jonah Hill. The premise is that Teller — a massage therapist with a pregnant girlfriend — gets sucked into a lucrative but unethical business selling arms to the US government during the Iraq war.

I didn’t finish the film, in part because the opening sequence irritated me to such an extent that it poisoned my view of the story. We meet Teller’s character after a business scheme fails and he is “reduced” to massage work, where customers demean him by requesting sexual favors. The film uses this scene to contextualize — even justify — his turn to arms dealing. (The film also leans on his girlfriend’s pregnancy, but I don’t think it’s an accident that the massage scene comes first.) To have a low-paying service industry job where sexual harassment is common, this film implies, is unendurable — for a man.
Emasculation, according to this film, means to be treated like women, who populate service industry jobs and who are frequently subjected to unwanted come-ons and all-out sexual harassment. And emasculation excuses immoral, dangerous, and selfish choices by men.
This film came to mind for reasons I couldn’t initially identify as I finished reading Fleishman Is in Trouble, the 2019 award-winning novel by Taffy Brodesser-Akner. The book follows Toby Fleishman, whose fifteen-year marriage is over, and who is finding his footing as a newly single man in New York. When his ex Rachel fails to pick up their two children at the allotted time — and then is unreachable for the next two weeks — Toby frantically arranges childcare while also fulfilling his duties as a hepatologist and maintaining his dating life. He also rages at Rachel, seeing her disappearing act as an extension of the selfish, work-focused behavior he dealt with as her husband. Now that he is out of the marriage, Toby, sees Rachel as little more than a stereotypical “crazy bitch,” and, as he notes, all he wanted was to marry a woman who wasn’t crazy.
So why did this book make me think of a forgettable Todd Phillips film? I eventually realized it is because Toby’s primary characteristic is emasculated self-loathing. He is short (5’5″), and from his teenage years he assumes women are not interested in him — which makes his newfound post-divorce sexual desirability novel and intoxicating. As we learn more about his marriage, we discover that Toby took on the stereotypical female “second shift” work. When Rachel’s career as an entertainment agent took off, his more predictable schedule and lower-paying job made him the logical choice to pick up the kids and make dinner. Toby tells Rachel that he wants to treat patients, not make more money, which is why he hasn’t sought promotion at the hospital. But it becomes obvious that Toby has been sidelined, his career stalled by his unwillingness to prioritize work above all else. He occupies what is traditionally the women’s side of the marital relationship: jobs filled by women tend to be lower- paid, which means it makes economic sense for them to take time from work manage the house and kids. (This dynamic is not immediately clear, in part because Toby’s job and salary as a medical specialist who makes a quarter of a million dollars would classify him as wildly successful to the vast majority of readers. But among the wealthy Upper East Side families with whom they socialize, and compared to Rachel, who makes fourteen times what he does, his accomplishments are underwhelming.) Rachel doesn’t emasculate Toby; the conditions of their marriage do.
Brodesser-Akner has chosen a curious narrative structure. The reader at first assumes third-person limited narration, until a first-person “me” creeps into the narrative. This “me” turns out to be Libby, Toby’s friend from college with whom he reconnects during his separation. Libby is (mostly) happily married with kids of her own, having abandoned a career writing at a men’s magazine. because, at this workplace, “Whatever kind of woman you are, even when you’re a lot of kinds of women, you’re still always just a woman, which is to say you’re always a bit less than a man.” When she and Toby reconnect, Libby finds a pathway to the person she used to be, before marriage and children and moving to New Jersey.
What is most remarkable about Fleishman in Trouble is the extent to which it uses Toby’s story to depict what it is like to be a woman who balances (or fails to balance) career ambitions with child-rearing. Through Libby, we eventually hear Rachel’s experience, which includes a searing scene in which she must apologize for implying that she, a woman who runs her own business and organizes her children’s social lives, works harder than her mom-socialite friends, one of whom has a house manager and who does not work outside the home. Libby, in a diatribe about working mothers, says that said “it’s just math” that being a working mother is more difficult than being a stay-at-home mom. Women cannot say so for fear of offending moms who do not work outside the home. Brodesser-Akner cleverly explains the focus on Toby through a comment from Libby: “That was what I knew for sure, that this was the only way to get someone to listen to a woman — to tell her story through a man; Trojan horse yourself into a man, and people would give a shit about you.” The difficulties encountered by Rachel and Libby are boring and well-trod; explore these experiences from a man’s perspective, though, and we have a story worth telling.
For Libby and Rachel, erasure is the primary experience of motherhood and middle age. Libby vapes in public because “No one was watching. People didn’t look at me anymore. I’m allowed to go into bathrooms that are only for customers now anywhere in the city. I could shoplift if I wanted to, is how ignored I am.” Rachel complains that, to Toby, her parenting work is invisible, saying, “All her contributions fell magically from the sky, or were born of something inherent in her female body.” Indeed, in Toby’s story Rachel is an absentee parent. Part of the issue is that Toby and Rachel define their parenting responsibilities differently. Rachel’s friendships with the other moms in their social circle are, she argues, cultivated for their kids’ benefit, while Toby sees them as just another example of Rachel’s desire for upward social mobility. But part of the issue, certainly, is that Rachel’s parenting tasks are expected, despite her work, because she is a mother.
Nothing Toby says about Rachel is a lie — she is materialistic, her work takes her away from her family, and she can be pointedly cruel. Toby, while occasionally self-righteous and prone to see himself, uncritically, as the put-upon party in his marriage, is no villain. The problem, as Libby puts it, is “the math” of being a full-time employee with career ambitions as well as a caring and involved parent. Toby and Rachel each believe themselves the victims of this dynamic, and neither of them is necessarily wrong.
I recommend this novel, two-thirds of which I read in an insomnia-fueled binge and which I’m still thinking about.