As much as I have loved Broad City, Abbi Jacobson and Ilana Glazer’s show about two funny, Jewish 20-somethings making it in New York, I was a bit off of season four last year. It wasn’t the fault of the show, which is a brilliant ethnographic expedition into millennial girls. It’s like an S. Ansky dive into the shtetl, but with laffs.One hilarious season four episode seemed emblematic of this problem. Ilana, unable to have an orgasm, goes to a sex therapist. She’s diagnosed. It’s Trump’s fault. Then, as in a comic book, a pantheon of female superheroes (including Hillary Clinton) appear to save her. Kaboom! Still, the show’s insouciant rags-to-semi-riches and wacky fourth-wave feminism was less watchable in our mean new political era. (The show will end after a fifth and final season in January.)So when, post-#MeToo, post-Kavanaugh, I started to read I Might Regret This, Jacobson’s new graphic breakup road-trip memoir, I worried that I would find it to be just one more memoir-by-girl-comic gimmick. We are at a strange cultural moment in publishing: There are now so many of these memoirs that we seem to have stopped having the conversation about whether women are funny. On the other hand, the publication of these memoirs has done nothing to stop misogyny.Told in the voice of a humbly sweet, disarmingly doofy young woman like the character Jacobson plays on TV, I Might Regret This is less pretentious than Lena Dunham’s That Kind of Girl. It is less defiant and less raunchy than Sarah Silverman’s Bedwetter. It is better written than Amy Schumer’s The Girl With the Lower Back Tattoo, published last year, but not as funny as Tina Fey’s Bossypants.The biggest thing separating I Might Regret This from the girl-memoir pack, however, is its grayscale drawings. Jacobson went to art school and in 2016, she produced Carry This Book, a best-selling pictorial rendering of the contents of people’s pockets and wallets. (Trump carries “Building Walls for Dummies.”) In a cool bit from season one of Broad City, an animated drawing Abbi sells to a whites-preferred dating website runs on TV at the moment she is trying to convince some woke African-Americans that she should sublet their spare room.In I Might Regret This, the drawings do more than illustrate what Jacobson ate, drank, or saw on the road. They act as a supplemental interior monologue. Or they redirect the reader’s attention, translate the sometimes haiku-like prose into visual puns. Even when they are aspirational, as when she draws the covers of Susan Sontag’s Against Interpretation and Joan Didion’s The White Album, I believed them. I believed that she read the books on her trip and that they meant something to her.But I had more trouble with the actual writing, what little there is of it. This is in part because Jacobson is strangely evasive, for a memoirist. She feels like a cipher. The reason for the book, the personal crisis that the author underwent—Jacobson fell in love for the first time with a woman and then broke up with her (or was broken up with, it’s not clear)—is underdrawn.“I can fall in love with Prince Charming or Princess Charming because Hollywood is changing,” she declares as in an advertisement for #MeToo. Maybe Jacobson is just discreet (not a quality I associate with memoirists). But I think it’s also possible that she was unable to free herself from one of the rules of the Upright Citizens Brigade, where she studied improv technique: Never talk about the past. The problem is that, in writing, that generally doesn’t work.In part because Jacobson gets confused about how much of herself and how much of her character to draw from, her attitude toward, say, her Jewish roots, can sound clichéd. It’s clear enough that on Broad City, Abbi is the introvert, the straight-haired Main-Line Jew that Ilana Glazer, the Long Island one, keeps asking if she is Jewish (because anyone with hair like that can’t be). But in the book, the title of the first chapter is a question that could have come from anyone’s Jewish mother, in many eras: “What’s the Worst That Could Happen?”The “worst happening” is an idea Jacobson rejects over and over. That’s partly for comic effect. But it’s also realistic. The worst that could happen often does.So in the charming, slightly twee Chapter 2, Jacobson gets a love letter postmarked Dec. 2, 1944, and spends considerable energy trying to return it to its rightful owner, using “non-Internet” gumshoe techniques. The real ending to this story is less romantic than the one she imagined. But she is unfazed. Or maybe a better way of putting that is that she prefers her comic vision to reality.Once she actually gets going on the road, she is able to juggle darkly hilarious collisions with reality, neo-shtetl humor, millennial ADD, and political memes. She is a kinder, gentler, Larry David, a prettier Seth Rogen (sorry, Seth). She skittles between her ingenuousness, her ingenuity, and her life. First stop Asheville, North Carolina. Here again, she draws from improv techniques she learned at the Upright Citizens Brigade. Having booked herself into a bed-and-breakfast, Jacobson realizes she has made a category error. She wanted to stay at an inn, like the one on the Gilmore Girls, not a B&B, where you have to eat scones and drink coffee in cups with saucers with other people.That’s funny enough. And, for once, she does riff about the past, diving into a long diversion about the kiddush cup from her childhood: “Being Jewish is all about asking questions, and my curiosity was piqued: Did water become holy because it was in the cup? Would it be OK to put ice in it? Would I dare use it to eat ice cream out of? Would people be intimidated if I was using the cup in a casual manner at the kitchen table?”I began to warm to these loopy, stoner, improv-based detours. But I still wanted something more literary, something more revealing. And then I would read things like the chapter titled “On Snacks,” followed by a listicle where there is a perfect meeting of form and content. The title, an homage to Sontag, surveys the snacks available in the lobbies at different comedy networks.Comedy Central: She doesn’t mention the snacks because “pictures of Me Are Everywhere.”HBO: “There is nothing in the lobby (food- or drinks-wise) and no one asks you if you want anything.”Amazon: “I might have had to sign a nondisclosure agreement to even enter the parking garage here. Also has “abundance of pink and red Starburst.”Jacobson’s tour of Memphis, Austin, Marfa, Santa Fe, Sedona, Jerome, and Palm Springs only occasionally hits the clever notes of the lobby tour. At times (and this is another problem with translating long-form improv to the page), Jacobson doesn’t know when to stop. I could have withstood fewer details, for example, about her insomnia. And I would have liked more details about her and the love affair driving her. We learn about her anxiety-driven fantasy of seeing her ex while getting her hair cut or in the middle of chewing an extra big bite. But nothing about the love affair itself.In fact, we learn a lot about anxiety and worrying about the “worst that could happen,” which seems essential to Jacobson’s definition of her Jewish roots. In “Minor Regrets,” written en route from Marfa to San Antonio, she waxes guilty that she was not more Jewish growing up. Maybe that guilt is Jewish, she thinks! Then, rushing on to another regret: not having sex with a guy in the bathroom after a bar mitzvah where she was working. Maybe sex is Jewish!There is a whole chapter on bagels. And the book ends on a Jubu moment as Jacobson visits a wellness center in Sedona. As usual, she starts off sarcastic, shooting gefilte fish in a barrel. “Nothing says tranquility and enlightenment like a hard-core itinerary.” But at a reading of her chart, she is unexpectedly moved. “From that poorly lit room on the top floor of a tiny mini mall in Sedona, a stranger told me exactly what I knew already.”What was that exactly? She describes knowing that she was different from other girls because her ambition isolated her from thinking about marriage. “I was preoccupied daydreaming about being on SNL, or having a one-woman show on Broadway like Gilda Live.” Does that ambition have a happily-ever-after for nice Jewish girl millennials? “If I learned anything, it’s that hopeless romantics don’t give up after they get one seventy-year-old letter in the mail and it doesn’t go as planned.”***You can help support Tablet’s unique brand of Jewish journalism. Click here to donate today.