The Best-Laid Plans

In You’re Leaving When? Annabelle Gurwitch laughs at the vicissitudes of life.

annabelle gurwitch, youre leaving when
Jason Rothenberg

Annabelle Gurwitch is funny. She is wry, witty, and a master of the bon mot. The author of numerous books—and once, the “resident humorist” for the Nation, a publication not known for its hilarity—she is also an actor, a podcaster, an NPR commentator, and a television host.

Her new book, You’re Leaving When? Adventures in Downward Mobility, gathers a series of connected essays that will make you laugh out loud. “There is no upside to downward financial mobility,” she writes in her introduction, “but there is value in reassessing priorities.… I’d hoped to one day get my kitchen remodeled; instead, I had my vagina reupholstered.”

As Erma Bombeck once observed, “if you can’t make it better, you can laugh at it.” In You’re Leaving When?, that’s precisely what Gurwitch does. As the book begins, her life is in tumult. Her husband leaves her, her parents die in quick succession, her college-age child goes into rehab, and she loses her union health insurance. For some writers, this might lead to a meditation on grieving. Gurwitch, however, goes a different way. She ends her litany of loss with the phrase “and my tennis teacher fired me,” as if that sums it all up. And it does. She tells us that she understands the teacher’s motivation: she was always late and wept through her lessons.

Five years of tennis. Twenty years of marriage. Gurwitch encourages us to laugh about the one even as we know she is weeping over the other. Because she is struggling financially, she investigates renting out a bedroom, wondering as she reads about another woman who has done the same, “What kind of gloves does she wear when disposing of the odd used condom? What face when she discovers a web of hairs of unknown origin clogging the shower drain?”

This is not a romp through privileged Los Angeles—despite her experience with vaginal rejuvenation. These are scary stories of a woman in middle age in America in 2021, too young for Medicare but too old to get that tenure-track job at a fabulous university.

Eventually, Gurwitch reluctantly rents the room to a young couple with face tattoos and a pet rabbit. At first, she hides her valuables and sleeps with “the rusty hatchet from the garage” under her pillow, but soon she and the couple are sharing meals and talking about their lives. Gurwitch’s warmth and empathy are apparent. When her now-sober child visits from college, she worries about her lodgers offering drugs and especially tattoos, but instead she finds her house “filled with music, chatter, and dad sneakers”—a fashion trend she finds especially endearing.

The essays in You’re Leaving When? cover Gurwitch’s transitional period: married to single, full-time mom to kid in college, upwardly mobile to financially and professionally at sea. She accepts other roommates, some good, some not so good. She travels for work. She has great friends and a family that loves her. Along the way, she begins to realize that she was the source of drama at every family event—dressing inappropriately or running out of gas and not showing up at all. In addition, she and her ex bickered constantly, which “ratcheted up tension around the dinner table.”

It’s funny on the page although not necessarily in real life, and Gurwitch understands this. At her first solo Thanksgiving, she recalls “the oxygen [she] typically sucked out of the room” and undergoes a change, using Millie, her nephew’s dog, as a catalyst. “Hadn’t I allowed Millie to lick my face, something everyone found adorable?” she remembers. “Didn’t that count as a ceding-the-spotlight personal growth triumph?” She is aware that her behavior, charming when she was young, now makes her the “eccentric aunt.”

Resilience. Determination. Gurwitch is not a woman to collapse on the chaise with hand on forehead while waiting for a man to rescue her. Men, in fact, have become a terrifying prospect. “I’m worried,” she confides, “that my middle-aged sex face might look too much like my I’ve-sprained-my-ankle face.”

With the help of her friends and sister—and the Pleasure Chest, where she buys a new dildo—she explores the secrets of sex after menopause. Too many details? Not really. No one else is writing about this, and Gurwitch is aware that spending nearly three grand on vaginal rejuvenation is more than most women can afford to do. Throughout the book, she remains self-deprecating, chagrined to complain about her life when so many others have it so much worse.

Not every essay in You’re Leaving When? is completely successful. “They Got the Alias That We’ve Been Living Under” details too many films about middle-aged women, starting in the 1970s; while there are clever thoughts, none of them are really new. “Dear Girlfriends” is a great idea—a series of emails to a dwindling group of friends—and very funny. It stops the forward movement of the collection, however, as if a very successful writing exercise had been dropped into the middle of the book.

But then there are the three essays about her nonbinary child, Ezra, almost the last pieces in the book. They are mesmerizing. Ezra—who uses the pronouns they, theirs, and them—was born with a rare collection of birth defects that required regular surgeries and other interventions in early childhood, and they share their mother’s grit and fortitude.

These pieces are less comedic than the other essays in You’re Leaving When?, revealing the pain and fear and sleepless nights involved in being the parent of an addicted child. In one, Gurwitch decides that an escape-room afternoon will create a wonderful bonding moment before her barely sober child goes back to college. The account is absurd and hilarious and sweet. She chooses a zombie-themed room because “zombiism seems like an awfully good metaphor for motherhood. Once you’ve got it, your life as you knew it is over and you’re destined to spend the rest of your days under its spell.”

It’s no surprise that things don’t turn out as planned, but it is Ezra who saves the day. In so doing, they achieve, perhaps—like so much of You’re Leaving When?—what Gurwitch has desired all along.•

Counterpoint Press
YOU'RE LEAVING WHEN?: ADVENTURES IN DOWNWARD MOBILITY, BY ANNABELLE GURWITCH
Counterpoint Press Bookshop.org
$23.92
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