Jacobson tells New Times writing the book was "a very cathartic experience." She's currently on a book tour after wrapping up the fifth and final season of Broad City and will talk about her tome Saturday, November 17, at the Miami Book Fair.
I Might Regret This follows Jacobson across the country on a heartbreak-induced road trip in June 2017 as she realizes she is not at all a bed-and-breakfast person, struggles with insomnia, and recalls stashing weed in the Kiddush cup from her bat mitzvah. Through her essays, she fills us in on her journey from the suburbs of Wayne, Pennsylvania, to art school in Baltimore to her short-lived enrollment in the Atlantic Theater Company. After realizing it's not for her and dropping out, Jacobson attends an Upright Citizens Brigade show at the suggestion of a roommate (who would later become the inspiration for Abbi's uncomfortable living situation on Broad City; suffice to say the two don't talk anymore).
"I found a seat in the back and watched a show, about what I couldn’t say, but I sat there in complete awe, paralyzed in a new way. This. This thing, whatever unexplainable thing they were doing on that stage, I wanted
She began taking classes at Upright Citizens Brigade (UCB) soon after, and there she met Ilana Glazer (whom she initially, hilariously, mistook for Alia Shawkat from Arrested Development). Their real-life relationship is every bit as fulfilling to read about as is watching the fictionalized version unfold on Broad City. Jacobson recalls feeling giddy as she waited for her train home after first meeting Glazer, "this brassy girl with big opinions, bold, animated, and who seemed to know exactly who she was."
For years, they worked on their improv together in New York City basements while holding down an array of random jobs to pay the rent. They continued auditioning for Harold teams, a coveted position in UCB composed of eight people (usually only two women
But Jacobson knew she was funny. She knew she was good. So rather than
"That frustration transformed into 'Fuck this.' We set out to do our own thing, partly as our only option, but also to prove ourselves to the institution we so badly wanted to be allowed inside," Jacobson writes. "It was like a door opened, but one we first built and nailed into the wall."
In the fall of 2009, they set out to make a web series, shooting in pizza shops and their apartments on weekends and evenings after work. Soon they developed a cult following. What Jacobson and Glazer were doing clearly resonated with people. They were giving women and female friendships representation that was so often left out of the usual fictionalized distaff depictions.
After a series of setbacks, they caught a big (and well-earned) break when they persuaded Amy Poehler, one of the founders of the UCB and an established comedian, to guest-star on the web series finale, in which she runs alongside Jacobson and Glazer as they race through New York City to get a cookie. From there, Jacobson mustered up the courage to ask the Parks and Recreation and SNL alum directly if she wanted to produce the show for television, and Poehler was in.
Poehler also gave some of the most practical advice Jacobson has ever received: "This is one of the things that Ilana and I talk about a lot," Jacobson tells New Times. "It's something that Amy Poehler said to us: 'Sometimes you have to treat yourself the way you would treat your daughter. So if you're feeling down or really doubtful about something not going the way you wanted it to, you have to be kinder to yourself, because we tend to be harsh on ourselves.'"
Fans of the show would be shocked to know FX turned it down for being "too girly." Though the Broad City ladies can be tomboys and certainly show a much "gnarlier" side of women (as Glazer would say)
"I think that that word doesn't have to be negative. It's not girly, but it also is too, in like a good way," Jacobson says.
Eventually, the show was picked up by Comedy Central, and when readers set out on the road with Jacobson in I Might Regret This, the fourth season of Broad City has just wrapped. Now she has no distractions from the heartache she'd been quietly struggling with the entire season.
So she drives across the country. And though she might have felt she was running away, the extended time with herself and her thoughts forces Jacobson to reflect on what happened and what it means for her. At 33, Jacobson had resigned herself to believing maybe she just couldn't get that close to people. Maybe she wasn't capable of love.
Then she met her — the woman who changed everything.
"I fell, completely out-of-control in love with this person, right then and there in that hug. In that hotel room. I was a goner," Jacobson writes. "Being out of control in love is glorious... It’s the closest thing we have to magic."
Jacobson is still careful. She never once names the person she was in a relationship with, nor does she get into details of why it ended or the problems they faced. Instead, she concentrates on something far more universal: the shock of meeting someone who upends everything you thought you wanted, the "dual-skydive of glee" of love, and how it "clobbers" you when it ends.
“It’s the most terrifying thing in the world for the person you love to suddenly stop, to disappear, and not want to be in your life anymore,” she writes. “What do you do with that?”
As she winds her way across the country, Jacobson is often plagued by insomnia. When she lies down to sleep at night, her mind won't leave her alone. It runs on and on and on, thinking of things big and small, fixating on tiny slivers of light as the culprit of her wakefulness.
One night in Utah, unable to sleep, she gets up and wanders deep into a field while clutching a wooden buffalo key chain and wearing mismatched pajamas. "I just stood there looking up at the sky, not remembering, not worrying, not planning," she says.
She lets time slow down as she gazes at the star-filled sky in the middle of nowhere. The stars "make you feel that the world is so much more than you ever could have thought, that maybe you'd only been focusing on a tiny little corner," she writes.
"I could see
Comedy Central’s Abbi Jacobson Might Regret This. 10:30 a.m. Saturday, November 17, at Miami Book Fair 2018, Miami Dade College Wolfson Campus, 300 NE Second Ave., Building 2, First Floor, Room 2106, Miami; 305-237-3258; miamibookfair.com. Admission is free with entrance to the street fair, which is $10 for general admission, $5 for ages 13 to 18 and over