It’s Halloween night, and young adults stream through the Chevalier Theater’s open doors. Some are dressed in traditionally spooky garb: witch hats, black. Others are costumed as Abbi and Ilana from Broad City; crop tops, scrunchies, and pigtails abound. These Halloweeners are all congregating in a small town on the outskirts of Boston to attend the second stop on Abbi Jacobson’s book tour for I Might Regret This, her collection of “essays, drawings, vulnerabilities, and other stuff.”

Onstage with Boston Globe reporter and fellow Jewish lady Meredith Goldstein, Jacobson is personable, sharp, and at times, self-deprecating. Her comedic timing is exactly what you would expect from one of the creators/writers/stars of Broad City: spot on. During the two-hour event, she answers questions, discusses the literal road she traveled in order to create I Might Regret This, and reads a short passage from her book to the audience.

During the summer of 2017, after filming the fourth season of Broad City, Jacobson embarked on a three-week solo road trip across the country. On the road, she listened to music, took photos, kept notes, and visited parts of the United States that, believe it or not, are good for more than just flying over. (“Maybe I should plan a road trip,” I thought to myself more than once while reading. “Do I know anyone in Utah?”) Out of these odds and ends, I Might Regret This was born.

Organized by trip leg, Jacobson’s collection is an “emotional journey” that mirrors her cross-country drive. Between New York and Asheville, she sets rules of conduct for herself during her trip: “Stay hydrated.” “Find silence wherever you can.” “Don’t listen to Sia’s ‘Breathe Me’.” (Yes, Six Feet Under is Jacobson’s favorite show.) On the drive from Asheville to Memphis, she asks the big questions because “being Jewish is all about asking questions”: “Are we living in a computer simulation or what?” “Why do so many people hate women?” On the leg between Santa Fe and Kanab, Utah, she lists adult concerns: “Are scrunchies back?” “Climate change.” Between these lists and questions are essays and drawings meditating on everything from growing up in Pennsylvania as a young Jewish girl to becoming comfortable with being alone. Some are hysterical, others heartbreaking.

Although Jacobson’s collection is infused with humor, her broken heart acts as the driving force behind I Might Regret This. Onstage at the Chevalier Theater, to an audience of hundreds, she explains that she made the decision to hit the road alone because she was overworked, overwhelmed, and fresh out of a relationship with the first person she had ever loved. “No one knows I date women,” she says. “Everyone assumes I’m straight.” Judging by the soft murmurs of surprise that arise from the audience, many in the crowd assumed so, too. Jacobson clarifies that although she’s out in her own life, the world has made heteronormative assumptions about her sexuality. “There’s hardly anyone in Hollywood who’s queer,” she notes. Or at least, queer and out. Now, Jacobson can proudly count herself among them.

As much as heartbreak influenced her essay collection, so too did her relationship with Ilana Glazer and her work on Broad City. As she explains to Goldstein, “The longest chapter in the book is about Broad City and to Ilana.” Jacobson has been working on the series for nearly ten years; it’s no wonder her work on the show and her relationship to her character have impacted her growth as an artist and as a person. In the Chevalier, Jacobson confides to the audience that it has been dizzying to hear fans of the series claim to feel like they know her, blurring her real-life identity with her character’s. Although they share a name, Jacobson and her fictional self are not the same. “I’m more introverted in reality,” she says onstage. “Abbi and Ilana are exaggerated, five-years-younger versions of me and Ilana.”

Jacobson has this to say to the crowd about the show’s final season: “I’m really proud of it. It’s okay that it’s ending. It’s okay that things end.” It’s as if the process of roadtripping across the United States and writing a book has led her to this exact realization; she’s reassuring herself as much as she’s comforting the audience. I hear faint sounds of approval around me. It works.

Jacobson calls I Might Regret This the kind of book she would want to read, but acknowledges that, like everyone else, she doesn’t know what she’s doing. “This is the hardest thing I’ve ever done,” she says to Goldstein. “This book could be a total failure.” It’s not. Give it a read. I promise you won’t regret it.

Thanks to Brookline Booksmith for co-sponsoring this stop on Abbi Jacobson’s book tour with the Jewish Women’s Archive. I Might Regret This is one of JWA’s 2018-2019 Book List picks.