Chloe Caldwell Mines The Messy Glory of Her Twenties

In the valedictory essay of her new collection, I’ll Tell You in Person, Chloe Caldwell recounts a trip to Berlin during which she attends a street rally. She’s proud to have punctuated her otherwise aimless stay with meaning, only to realize she’s unclear as to the protest’s cause.

If this isn’t an encapsulation of twentysomething meandering, I don’t know what is. Caldwell’s reputation as a chronicler of just that experience gets another nudge from her new book — this following an earlier glittery essay collection, Legs Get Led Astray, and an autobiographical novella, praised by Lena Dunham, about falling in love with a woman. I’ll Tell You reads like a coda to her years spent bouncing from city to city, job to job, and BFF to BFF. “I was always aware that this time would prove fleeting, and felt I had to try different things,” Caldwell, who turned thirty this year, tells the Voice. “Eventually I decided to build a life because I didn’t have anything. I didn’t have a lamp.”

But stumbling around in the dark can make for good stories. In “Prime Meats,” Caldwell describes working at a jewelry store on Bleecker while her friend Ana manned the sister shop across the street. They’d pass entire shifts chatting via walkie-talkie and then go out drinking, one night returning to the store to sleep on the floor beneath a fur coat. Of their dive of choice, Caldwell writes, “Like everything we did, going to Wogies began as a joke, and then a year went by.” The essay title refers to a Craigslist ad the pair posted seeking men who would buy them steak and scotch. If this was unsafe, it didn’t seem that way, simply because they were together.

Friends take on protective powers throughout. Another essay looks back to Caldwell’s high school years, when she found refuge from her parents’ separation among a group of guys who shared a fondness for weed and Top 40: Nelly and Nelly Furtado and the American Pie soundtracks. (Readers of a certain age and suburban milieu will also thrill to mentions of Baby Alive, ElimiDate, and Chi straighteners.) Pack-like, they paged through magazines in the lobby of Caldwell’s therapist’s office and talked on the phone in the middle of the night, unless they were already head to toe at platonic sleepovers. The strongest scenes reflect Caldwell’s preoccupation with the relationships we tend to discard — “people you don’t talk to anymore but who shaped you,” she says.

Abandoned pastimes also get some play, to varying effect. In “Failing Singing,” Caldwell recalls walking away from voice lessons and auditions, having found herself somewhere in between good and good enough. Like many of the pieces here, it’s more anecdotal than artful, though surely relatable to anyone who has ever quit anything and wondered if wanting it more would’ve made a difference. “Soul Killer,” in which Caldwell describes falling into a heroin habit while attending power yoga five times a week, packs more of a punch. A scene in which she gets high in an Urban Outfitters dressing room before attending her own book reading and falling into bed with an ex pays homage to the freewheeling-writer archetype. Others, like one in which she snorts heroin before driving to Stop & Shop to buy Light & Fit yogurt, are just plain grim.

Despite Caldwell’s brush with addiction, these essays don’t sit within the train-wreck subgenre. When a babysitting charge asks if she’s had a sad life, she says no. But this isn’t the work of an extremely well-known and wildly successful person either, as is so often true with tell-all collections by funny females. Caldwell is refreshingly regular and, German sojourn notwithstanding, unspoiled. She moved from upstate New York to Brooklyn instead of finishing community college, and not once does the word “internship” appear. When an unnamed famous writer (a thinly veiled Dunham) plans to visit her, Caldwell is racked with anxiety and feelings of shabbiness. What’s more, she doesn’t ask us to find her adorable. There’s a line about how she reads books out of order (hasn’t Kate Hudson played this quirk?), but usually Caldwell adopts a non-performative, take-it-or-leave-it tone, as though she’s an old friend you’re catching up with over glasses of wine. Maybe you haven’t seen each other in a long time and stay late into the night.

Eventually, I’ll Tell You‘s featured drinking buddies give way to fellow writers, who understand and encourage Caldwell’s work in ways former boyfriends never could. “They were always pretending to get it,” she says, adding that she’s sometimes had to fight the impulse to apologize for taking up space. One essay details her budding friendship with the grunge-era slam poet Maggie Estep in the months before Estep’s unexpected death. “We put sticks of gum and rose petals in the casket,” Caldwell writes of this hit of grief and sobering reminder of mortality.

Unsurprisingly, Caldwell’s vices are now milder and her ambitions clearer. A self-confessed TV addict, she loves Difficult People and “anything Jill Soloway touches” and is looking forward to Pamela Adlon’s Better Things. Someday she hopes to ditch her freelance lifestyle and join a writers’ room in sunny L.A., but who knows. As she writes about Cheryl Strayed, a pal whose work she discovered in The Sun Magazine as a child, along with that of Poe Ballantine and Sparrow, “There is one decade between us, and I’m curious what that decade will make of me.”

I’ll Tell You in Person
By Chloe Caldwell
184 pp., Coffee House Press
October 4