BEFORE I EVEN cracked the spine on Lauren Weedman’s Miss Fortune: Fresh Perspectives on Having It All from Someone Who Is Not Okay, a memoir in comedic essays, I knew the questions I wanted to address in my review. I’d admired Weedman’s work in the HBO show Looking and felt attached to her character, Doris. I imagined that, in contrast, I’d find her book lacking, and could use it as a springboard to discuss whether or not we hold celebrity writers to a different standard. How much does attachment to someone’s on-screen persona (in character or out) cause us to lower the literary bar?

But there was a problem with my plan: I genuinely enjoyed Miss Fortune. I found myself not merely smiling, but cackling — and, in turn, tearing up or sighing with sad recognition. Not that some essays aren’t stronger than others (particularly in the first half of the collection), but this book wasn’t going to serve to bolster my highfalutin musings about the inverse relationship between writerly skill and level of fame — or to determine how much bad writing I can take from an actress I love. Instead, my question turns out to be simple: why does Miss Fortune work? The answer lies in the delicate balance between humor and sincerity.

Miss Fortune is “based on my life,” Weedman writes at the outset. “It’s true, but I’ve also exaggerated a bit for the sake of the jokes, in order not to cause any human harm, and to avoid being sued.” The book opens on Weedman’s relationship with a man named David and follows her through marriage, pregnancy, the birth of her child Leo, and a number of jobs (including a glancing mention of her brief time working on The Daily Show). Along the way, there are extended flashbacks to her youth, including her time in high school show choir and, in her early 20s, living in Amsterdam working in a hotel café and for an experimental theater company.

When humor in this kind of book doesn’t work so well, it’s used as a distancing mechanism — that is, it counteracts a memoir’s purpose, which is to allow the reader into the narrator’s psyche. At times, particularly toward the back half of the book, Weedman falls into this distancing rhythm, and the jokes fall flat because they aren’t anchored in something deep and real. (As when she writes in the essay “Strippery Slope”: “But you know what they say: It’s all fun and games until someone gets titties in the face.”) At other moments, she deflects attention from herself to focus on stories of, for example, random neighbors we don’t care about. But for the most part, Weedman is skilled at using humor as a way in rather than a diversion. Even and especially at her most hilarious, she’s willing to reveal her earnest underbelly.

A lot of the self-deprecation in the book centers on Weedman’s appearance and general attractiveness. I find her quite appealing — she’s a petite, blue-eyed blonde — but it’s clear she doesn’t. In “Love of My Life,” she writes, “All of Hannah and David’s friends are so attractive. Why is that? Do attractive people hang out with other attractive people so they don’t have to feel bad about never paying for drinks or newspapers?” And in the same essay I laughed aloud when I read, “My voice sounds like Godzilla’s footsteps.” It’s a good line, but it really lands because of the context: Hannah is David’s former wife, who died of cancer eight years prior. Weedman’s feelings about her looks are a manifestation of far deeper doubts about her relationship and worth.

In “I Like You. I Really Like You.” Weedman uses a conversation with David about their pasts as a segue to tell the story of her first and only threesome. “Once upon a time, I was a twenty-one-year-old American living in Amsterdam with the low self-esteem and poor personal boundaries that only a cult leader could love,” she writes. My margin note: “HA,” a likely phonetic reconstruction of the laugh/bark I emitted. Weedman was working in a café at a hotel; upstairs was the less-classy Breakfast Buffet. “Nobody else liked having to traipse up three flights of stairs,” she writes, “but even if there had been an elevator I would have volunteered, because only buying a jumbo box of tampons made me feel as solidly female as being sexually harassed by the Buffet Boys.” I love that she admits to enjoying harassment, not only because it’s a fairly subversive thing to say in our current iteration of feminism, but also because it’s undergirded by an honest account of deep insecurity and her craving for attention.

She meets up with one of the Breakfast Buffet guys, Emad, who brings along a friend. A lesser writer or humorist might use this essay as a “look at me, I’m wild!”–fest, but Weedman’s “crazy story” hook (in fact, the description of the threesome itself lasts less than a page) is tempered by her desire for connection and ambivalence about her choices. One of the two men, she discovers, has a brand-new family. “He had a newborn?!” she writes,

What kind of person left his wife at home with a newborn while he … ech. Ech-ech. Awful people making disgusting choices, and there I was in the thick of it. They shouldn’t call them three-ways. They should call them ‘piles of idiots.’

Nonetheless, she and Emad start dating, though the relationship is necessarily short-lived. “It had felt good to turn him down,” Weedman writes. “It wasn’t a hard call, but it still felt good, like proof that I’d finally taken control of my life.” Back in the present, in the car with David, she admits, “what I’d really wanted back then was some hand holding, a nice dinner, and tickling backs with one boring unmarried person.”

Weedman’s commitment to sincere exploration of the layers underneath the jokes extends to her discussion of work. Here, maybe, is where her level of professional success is relevant: Miss Fortune delves liberally into the difficulties of pursuing an acting career. Weedman is not an A-list celebrity, which distinguishes her from, for example, Lena Dunham, whose memoir Not That Kind of Girl was criticized for skating over her work life. Rachel Dry wrote in The Washington Post:

Dunham, it is very clear, has always wanted to make herself known. But she doesn’t explore that hunger for fame and attention or her working assumption, maybe drawn from her parents and their colleagues, that hers would be a public life. It is stated as fact, background noise.

How novel it would be to read Lena Dunham’s thoughts on the idea of failure: What would it have felt like to plod through every day confident that greater glory exists elsewhere?

Weedman, in contrast, addresses such issues head-on. This might stem from the fact that she didn’t rise to meteoric fame in her 20s, as Dunham did, but also feels in line with her forthright approach to her bodily insecurities, her feelings on marriage and motherhood, and all the rest. “Performing eight times a week for audiences that are shuttled in from their convalescent homes hasn’t quite been the diva-making machine that I’d hoped,” she writes in the opening essay.

During my curtain calls, I start mouthing “I’m sorry” as I bow to an audience of confused-looking old people. I’ve gone from deeply depressed to morbidly depressed.

After shows I start making videos of myself where I look in the camera and say, “I’m so lonely. I’ve never been so lonely in my life.”

In an essay called “Horny Patty,” Weedman gets the part of the eponymous character on the HBO show Hung. (At the audition, “The energy in the room is pretty heavy. All the actresses look so miserable. They’re all deeply focused on inhabiting the character of Horny Patty,” she writes. “It was so effortless for me to inhabit this sad horny lady that I walk out feeling … good.”) Again, she tackles work issues directly, writing with humor and realism on Hollywood’s sexist standards. She’s pregnant at the time, and worries about the way her changing body will affect her job — not to mention that she’s required to be nude for the part and happens to have an inverted nipple. “What does that mean?” her agent asks. “You know. It means that it doesn’t cut glass. The turkey’s never ready. Tokyo can’t tune in.” Funny. As is a later conversation, in which one of the writers asks her to wipe her only “makeup” — the Carmex on her lips — off:

“Should I go in the parking lot and throw some rocks at my face?” I suggest.

She squints her eyes, contemplating. “No. Not yet.”

We get a hint of the reason Weedman is so self-deprecating — about her looks, in particular — in an essay called “Skin on Skin.” She describes “the jail-cell violence” between her and her older sister. “[T]he warden who should have broken it up was an eighty-nine-pound ex-ballerina. My mother would sit licking rice crackers as my sister pinned my face down with her knee in the family room.” We later learn that Weedman was adopted, and that she also has a very complex relationship with her birth mother, whom she met at 19. Throughout, such revelations offer insight into the source of her shtick, a case study of the hothouse in which (defensive) comedy blooms. Again, because she includes an honest emotional accounting, rather than keeping her readers at arm’s length, she lets us in.

The book derives its subtitle from Weedman’s experience in Amsterdam in her early 20s. While there, she worked for a bizarre experimental theater company under the direction of Nico, an eccentric and unstable guru-type figure. “Lauren,” Nico tells her, “There are those of us who know in the deepest core of their being that they are Okay and there are those of us who have had a few doozies thrown our way and know in the deepest core of our being that we are Not Okay.” But it’s precisely Weedman’s commitment to owning her Not-Okayness that convinces us she is fortunate, indeed. As are we, for having spent time in her company. In fact, my original (snobbish) desire to use Weedman’s book as a pawn in my intellectual games is exactly the kind of thing Miss Fortune’s sincerity argues against. And rightly so.

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Jessica Gross is a writer based in New York City. She contributes to The New York Times Magazine, TED.com, and The Paris Review Daily, among other places.