Stuff I Read: Fleishman is in Trouble by Taffy Brodesser-Akner

A newly divorced father experiences a new life in New York’s Upper West Side via dating apps. But when his ex-wife disappears, leaving their two preteen children in his care indefinitely, it puts a damper on his escapades for the summer. Taffy Brodesser-Akner explores selfishness, parenthood, divorce, and dating in her debut novel, Fleishman is in Trouble.

Fleishman is in Trouble by Taffy Brodesser-Akner

Toby Fleishman is a moderately successful hepatologist in New York City, recently separated from Rachel, having agreed to joint custody of their two children. Rachel gets them most of the time, while Toby gets them on alternating weekends. This leaves the 40-something Toby to sample the dating pool for the first time in his adult life—only to find that he is in demand! To Toby’s great surprise and delight, the market for a middle-aged, divorced, nebbish doctor is quite robust. With apps like Tinder having changed the landscape of modern dating, Toby is having more dates (and sex) than he ever had previously. He also uses his newfound freedom to reconnect to his best friends from college: perpetual womanizer Seth, now engaged to a woman half his age; and Libby (our narrator), a former magazine writer who harbored an unrequited crush on Toby in college and is now a married mother herself. Neither of his friends ever really liked Rachel and are thrilled to reunite like old times. One weekend early in the summer, Rachel deposits the kids—sullen 11-year-old Hannah and good-natured 7-year-old Solly—at Toby’s apartment. While at first it seems like a normal weekend, it goes haywire when Rachel doesn’t return and is suddenly unreachable and casts an enormous disruption in Toby’s career and burgeoning sex life. Now he has to try to balance work, dating, and raising kids in the social media era.

There’s a lot to like about this story, and it starts with the main characters. Brodesser-Akner wisely makes observations about Toby and his world from Libby’s eyes. It creates a nifty parallel character development. As Toby’s life melts down, he becomes an increasingly unlikeable person, both to the reader and to the woman who crushed on him so hard 20 years prior. It highlights the absurdity of holding on to a version of yourself from so long ago through Seth, who is on a mission to maintain his youth by glomming on to someone else’s. And it shines a bright light on the hypocrisy inherent in parenthood. Toby is a doctor and a father, whereas Libby—a talented writer—merely describes herself as a mother. Toby is considered the struggling parent, inherently irresponsible, where Rachel is assumed to be better suited as a mother. All the main characters are in the midst of some version of a midlife crisis, and it’s all handled beautifully. I also enjoy that there is ample time spent skewering upper-crust New York stereotypes. Being a child of the city, it’s a particular kind of schadenfreude I can’t get enough of. Yeah, I’m petty. Sue me.

Any negatives I have on this book come in how certain female characters are handled. One is a woman Toby dates, initially a powerful object of sexual obsession who Toby thinks could be someone notable in his life. However, once she shares her backstory and makes herself vulnerable to him, he cools on her. I’m sure this was the point, one more stop in Toby’s slide from put-upon father to full-on asshole, but it felt a little ham-handed. On the other extreme, there’s an attempt late in the book to humanize Rachel by showing the time spanned in the book from her perspective. The intent seems to be about highlighting the difficulty of a woman balancing parenthood with a high-powered career. Given certain facts in the story, though, the attempt to humanize falls flat for me. I’d also be remiss if I didn’t note that this version of New York is somehow completely devoid of people of color. Only one named character, no background people, not even a doorman at one of the high-rises. That’s a detail that nearly breaks the spell for me.

Fleishman is in Trouble is a solid and fun read that makes smart points about dating, parenthood, having a high-powered career, and middle age, with modern New York as a backdrop. Alternating between clumsy and poignant, it’s a good read to start or end the summer or fall, even with my minor character gripes.

Pros: Good story, smart commentary, great character growth

Cons: Insular in its avoidance of POC; clumsy handling of certain themes

Rating: 3.5 out of 5 stars