I Might Regret This

Essays, Drawings, Vulnerabilities, and Other Stuff


By Abbi Jacobson

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This item is a preorder. Your payment method will be charged immediately, and the product is expected to ship on or around October 30, 2018. This date is subject to change due to shipping delays beyond our control.

From the co-creator and co-star of the hit series Broad City, a “poignant, funny, and beautifully unabashed” (Cheryl Strayed) New York Times bestselling essay collection about love, loss, work, comedy, and figuring out who you really are when you thought you already knew.

When Abbi Jacobson announced to friends and acquaintances that she planned to drive across the country alone, she was met with lots of questions and opinions: Why wasn’t she going with friends? Wouldn’t it be incredibly lonely? The North route is better! Was it safe for a woman? The Southern route is the way to go! You should bring mace! And a common one… why? But Abbi had always found comfort in solitude, and needed space to step back and hit the reset button. As she spent time in each city and town on her way to Los Angeles, she mulled over the big questions — What do I really want? What is the worst possible scenario in which I could run into my ex? How has the decision to wear my shirts tucked in been pivotal in my adulthood?

In this collection of anecdotes, observations and reflections–all told in the sharp, wildly funny, and relatable voice that has endeared Abbi to critics and fans alike–readers will feel like they’re in the passenger seat on a fun and, ultimately, inspiring journey. With some original illustrations by the author.


A Note on the Illustrations

As I drove across the country, so much of my time alone was spent listening to music and podcasts, and I wanted to include them here in the journey. Each album or podcast encompasses part of the country, and part of my experience. Visually, I wanted to express my love for the variety of incredible album art in my own illustration style, and take the time to appreciate the full impact and thought behind the covers as well as the music. I listened to more records and podcasts than those included, but these are some of my favorites. Maybe you’ll be inclined to seek these out yourself.


Before I make a decision, I tend to think about all the possible outcomes. I like to be prepared. This tendency unfortunately mainly includes obsessing over the ways in which things could go terribly off course, but it’s better to be informed. So, before embarking on a solo cross-country drive that I would then write about in a book, I made a list of possible worst-case scenarios. The road trip alone was terrifying, but writing about it afterward? A lot could go wrong. So, what’s the worst that could happen?


Heinous scenarios where I’m badly hurt or die that I won’t go into.


I adapt to eating only fast food while on the road and become someone who advocates for this new lifestyle. My politics change. I attend rallies for meat farms and even faster food. I go around encouraging people to stop caring, we’re all going to die anyways!


I become a car fanatic. I learn the lingo, up my horsepower, and create an Instagram account just for my cars. I become the young Jay Leno.

After having not spoken to anyone for three weeks, I lose my voice completely. I have to find a voice double to dub in my voice on every acting project, and one day, while on the subway home from work, I break down because I realize I’ll never become the singer I always dreamed.

I don’t make it to Los Angeles. I take a wrong turn and end up in a small town somewhere in the middle of New Mexico. My car runs out of gas, so I have to stay the night in the local motel. While wandering around town the next day, I stumble upon a little shack and see a “For Sale” sign out front. I buy it and decide that this is my new life. I meet a lady bartender when I go to her bar alone and play The The on the jukebox. She likes that band too and we spend the night together. She moves in almost immediately. Typical. I start to carve wood after seeing a local artisan carving wood in his garage and I become his apprentice. I’ve always wanted to try carving wood. We start the New Mexican chapter of the Competitive Dual Wood Carving Association (CDWCA for short) and beat anyone within a hundred-mile radius in the Annual Southwestern Carvers Competition (ASCC). Also, is dual wood carving a thing? Shouldn’t it be? I die next to my bartender, content, in our bed that I carved myself.


I get picked apart because driving across the country isn’t the best thing for the environment. Or because my almond consumption is exhausting water supplies, or anything else I’ve done or written about in this collection that is bad for the earth. I know. I know, I know. I’m a shit and I’m sorry. But what about the fact that half the country eats a fucking cheeseburger two times a week? What about that undeniable imprint and impact on the climate? We’re all monsters, including me and my almonds.


Everyone will be like, learn to draw hands already!


People read the book and think, “What is this crap? A privileged white woman writes about how she’s sad on her three-week vacation? Not for me.” I am those things, and I did exactly that. I’m in no way denying how completely insane it is that I get to take off work for three weeks and drive around the country and then write about it…as more work. My life is bizarre and confusing to me as well.


Even though the book will be copyedited and proofread, my terrible grammar and lack of sophisticated vocabulary will shine through.


No one buys the book! If no one buys the book, the publisher could make me buy all the copies and I’ll have to fill my apartment with books. I guess I could create furniture out of the books, piling them up like a sofa. I could throw pillows on top. I’ve had some time to think about this, and I could really make it work. Maybe my home, with its furniture completely built from my failed, unbought books, would make it into Architectural Digest? They’d come and take pictures and run a whole article about it. Who knows what could happen then!?

I’ll get called out for not listening to the right albums, for playing the wrong podcasts, for not queuing up the most perfect playlist for the entire trip…I did my best.


All the pages somehow get numbered incorrectly!

I write about what it was like for me to fall in love with a woman and how I was clobbered when it ended and then I get banished from Hollywood! I’ll never be the starlet I’ve always dreamed of, falling in love with Prince Charming on screen. FUCK THAT BULLSHIT. I can fall in love with Prince Charming or Princess Charming because Hollywood is changing. Anyone who only wants to watch the standard narrative better start collecting VHS tapes, because we’re changing things. I want to be a part of telling real, more diverse love stories, ones I haven’t seen on screen before.

That ultimately I’m admitting that I’m scared of being alone. But aren’t we all? Isn’t that…the main thing? Aren’t we all secretly terrified that we’re not understood, not seen, not loved, not wanted? Okay, great, cleared that up.


In February of 2013, I received a love letter from 1944.


I had been out in Los Angeles for a few weeks, compiling the writers’ room for Broad City and gearing up to start Season 1. I sublet my apartment in Greenwich Village to a friend of a friend while I was away, a sweet guy who watered my plant (hard T) and collected my mail. When I returned, I trudged up the stairs of my third-story walk-up with my luggage to find a large, neatly stacked pile on the kitchen counter. I’d never seen a few weeks’ worth of mail at once, and immediately got excited—I love mail, and with a stack like this, the chances of me getting something good were higher. I’m talking real mail—a handwritten note or postcard from a friend, a small care package from my mom or dad or grandparent.

Real mail leaves an impression because it’s an event—the surprise of receiving it, the examining of the envelope, and the reveal when you open it. It’s tactile and ritualistic. When I was about seven, my grandparents accidentally sent my brother and me a postcard from their trip to London with two punks in leather jackets holding up their middle fingers straight to camera—we teased them about it for years. My other grandfather was a sort of mail connoisseur—he wrote me letters all throughout college; sometimes the letter would be covered in stickers, sometimes there’d be cash slipped inside, and other times there’d be a magnet his bank gave him for free. When I was away at overnight camp each summer, he’d send me care packages with fake cardboard bottoms he fashioned himself—he owned an Army and Navy Store, so he was often “fashioning things himself.” There was always a letter included in the package, resting on top of the boring packs of sports socks or Hanes T-shirts (to throw the counselors off), with instructions on how to pry open the perfectly fitted piece of cardboard he’d cut with an X-Acto knife. Underneath the fake bottom was neatly arranged candy and prank toys for my entire bunk. I loved finding that hidden loot. But it almost didn’t matter what was inside the package, the act of receiving that loving gesture, directly from him to me, was enough. Now sending or receiving real, handwritten correspondence is like owning a classic car; it feels more thoughtful, curated, something you just want to run your hands along, but ultimately, it’s no longer the most efficient way to drive.

Even owning stamps seems bizarre these days. Imagine going to grab brunch with friends and someone says, “Hold up a sec, I have to pop into the bodega and grab some stamps.” Everyone would be like: “For what?” “Bodegas have stamps?” “Also, what are stamps?” I don’t think you’d even make it to brunch if they stopped to drop the letter in a mailbox. “You can use those blue things on the sidewalk!?” “I thought those were Banksys!?” We order more shit online than ever before and constantly get packages sent to us directly from the huge conglomerates taking over the world, but the thought of corresponding via snail mail with the people closest to us is absurd. What is happening to us?

The efficiency and speed of email and texting is something I obviously take part in and use, almost constantly, but the connection between us feels altered now. Like we never have to give more than part of ourselves when talking to anyone in any situation. We abbreviate, we rush delivery, we unsubscribe, we edit ourselves. When I was in college and communicating through social media was starting to really take off, for the first time, you could connect immediately with everyone you’ve ever met and anyone you haven’t yet with one drunken click. Yearning for something more substantial, I did a project where I sent handwritten letters to twenty strangers in twenty different cities all over the country, to test what would happen. I found them randomly in the white pages, and shared something personal with each of them, a story about myself that was in some way associated with where they lived. I included another envelope (stamped already) with my address and asked them to write back sharing something of themselves with me. Would a connection be made? Would they, too, appreciate the long-lost art of letter-writing? Would this be the beginning of lifelong friendships and paper cuts (from opening so many envelopes)!? No, it wouldn’t. One person wrote back. A teacher and soap maker who had gone to art school and appreciated my curiosity. I’d written her about my experience at a restaurant in the Bay Area called Burma Superstar, and how my dad and I didn’t order, but rather let the waiter bring out whatever he thought was best. I told her about how I’d never done that before and how it was one of the most delicious meals of my entire life. She sent me back a short, sweet note about the birth of her two children and how those days were her most memorable, her most remarkable. And that she too loved Burma Superstar. The experiment didn’t go exactly as I’d hoped, but that one letter was enough for me. A small, meaningful connection with a stranger in San Francisco, for no reason at all. So, it would make sense then, if you believe in destiny (jury’s still out!), that a lost, seventy-year-old letter would end up with me.


Los Angeles had been thrilling—but also overwhelming, and I was excited to be back in New York. I sifted through my pile of mail, relieved to be home, relieved to be doing anything mundane in my space, but disappointed as it seemed to be the usual suspects, junk mail and bills. More specifically, it was mostly advertisements for stuff I didn’t need, stuff I didn’t want, or stuff I couldn’t afford, a casual reminder of exactly where I was in my life: Coupons for Buy Buy Baby? Nope. AARP membership information? I’ll pass for now. A catalog for Bose sound systems? Thank you, but my studio apartment with French doors (fancy) leading directly into my…BED does not require any speakers as the square footage is so small the audio leaking from my headphones does the trick. That’s how the Realtor should have sold it—who needs room for a sofa when it’s so easy to fill the space with music?

I saved the Con Ed bill, the Design Within Reach (if your arm is a mile long) catalog as décor porn, and the Bed Bath & Beyond coupons for good measure—I had to stock up on trash bags to dump all this junk mail, so I might as well get 20 percent off. But then, just as I was about to toss the rest, an envelope caught my eye. I’d never seen one like this: an eight-by-ten envelope that was from the post office, like THE postal service, with a transparent window on the front that you could see through. Inside, there was a smaller, yellowed-with-age envelope with old-timey cursive handwriting. Not to put cursive in a category, but it was grandparent cursive. It’s different, it’s thoughtful, it’s beautiful. They were taught to write more formally than we are now, and even though I remember practicing cursive as a kid, tracing the letters on worksheet pages, no one cared. There was no follow-through with handwriting. Am I from the last generation to even trace those cursive letters? Are children still taught handwriting?! I imagine kids nowadays come into school and set up mini cubicles, adjust their standing desks and writing tablets, everyone jacked up on five-hour energy shots, checking their social media in the middle of math class, taking selfies while their hologram teacher goes on about fractions in the background. I clearly don’t have children. I’m jumping ahead (there aren’t hologram teachers, right?), but handwriting feels almost ancient while we download and update by rote to the latest versions and systems and software. Everything is on screens now, and it all feels so immediate, and so fleeting. The more we rely on intangible pixels floating around, the harder it is to pinpoint what is real. This constant connection is distant, and actually, disconnected.

The aged, worn envelope with grandparent cursive on the front was postmarked December 2, 1944. WHAT NOW? How was this happening? At first, I thought it might be some weird prank, or mistake. How was this being delivered in 2013, almost seventy years later? I had so many questions: The letter had been opened, but why was it sent again, now? Had it ever gotten to its rightful recipient? How had a postal worker seen this and not been as fascinated as I was? Were letters like this floating around, re-sent all the time so it was just a common occurrence? Was I a character in a Nicholas Sparks novel?!

The note inside was a love letter from a lieutenant, Joseph O. Matthews, to his wife, Betty, who was living in my apartment on MacDougal Street while he was deployed. Joseph was at Camp Lejeune, a military base in North Carolina, and this letter was sent right before he was shipped off to the war in Okinawa. It wasn’t excessively romantic, he didn’t write about being afraid or longing for her touch. But it was intimate, and sad, beautiful and simple. A brief look into their relationship, their dialogue, their shorthand, without overly acknowledging the weight of the situation.

As much as I knew I wasn’t involved in this soldier’s handwritten note to his wife, I felt I was being pulled into their story, their private life for a moment. Who were Joseph and Betty? What happened to them, and what was this love story that had existed in the same room I was sitting in?

There were a few ways in which I could proceed in a scenario like this: (1) I could brush it off. The postal service is clearly disorganized—they keep sending me elderly membership cards and diaper discounts. This letter slipped through the cracks—weird, but who cares? (2) I could tell a few friends and save the letter as a keepsake, a fun conversation starter. OR, (3) I could see this as an adventure, and follow the clues from an old piece of paper for no reason other than curiosity.

This felt like the type of thing that could only happen in New York City—a twist in time, a clumsy mistake in the system, a lost letter landing in the hands of a hopeless romantic. If that’s not a movie (CONTACT MY AGENT) I don’t know what is. The city, traced through the history of one apartment, one tenant to another. Maybe I romanticized it, maybe I blew it up into something bigger than it was, but this city has an energy, a lifeblood that beats and pulses and makes you feel like you’re a part of something. I’d just gotten a seventy-year-old letter sent to me in the mail. I was a part of something! It felt like magic. On top of that, my grandmother Estelle was from Brooklyn, and grew up there in the ’20s and ’30s. I don’t know a lot about her life in New York, but this made me feel closer to her—the date on the letter was only a few years after she would have lived there, and this couple was her age. I imagined what it might be like to see a correspondence from her back then, recirculated into existence. Who was she writing love letters to? What did she think about and worry about? Did she trudge up the stairs to her third-floor walk-up, looking through her stack of mail hoping for something good? Did she see the city like me, and wander the streets to lose herself in thought? Did she struggle with hair removal and what was the best and least painful way to go about it too? If her letter was out there, lost, I would want someone to find me.

So, I decided to Tom Hanks it. I Cast Away’d it. I WOULD DELIVER THIS LETTER IF IT KILLED ME!


When I knew I was going to deliver the letter, I got in touch with my friend Todd Bieber. Todd and I had known each other for a few years, we met auditioning for improv teams (neither of us got on one), but we’d hung out in the comedy community ever since. In 2011, while cross-country skiing during a blizzard in Prospect Park, he found a roll of film in the snow. He then documented his journey to find the people who owned the film; developing it and posting some of the images and information on where and when he found it online, imploring the internet for help. Thousands of people responded, and his project went viral. He traveled to Europe on a wild adventure, meeting new friends along the way who offered to put him up in their apartments or take him out for drinks. He documented his entire, inspiring experience. I remember watching his video online, it was so exciting—he made something incredible out of nothing, out of merely being curious. He returned the film to its rightful owners, but the story became way bigger than just them. He could have walked right past that film, not developed it, not given it a second thought, but he didn’t. He saw a possible connection, something outside his normal life. I knew he was the guy to help me, I could be his next documentary about found things being returned.

Todd filmed me talking about the letter, about my hopes to find Joseph or Betty or their family, and about my excitement in general to begin whatever this was going to be. Maybe we would deliver the letter to an adorable old couple, living together in one of those tiny but perfectly lived-in New York apartments—the ones where every single thing in the room has its own story. Maybe there’d be photos of their family lined up on the mantel, evidence of their life since this letter was written? Maybe we’d get to see the love story closer to the end and then hear how it unfolded? You almost never get to see real love stories closer to the end.

Besides figuring out which songs this elderly couple and I would sing together accompanied by their in-home grand piano, and what pastries I’d bring along, the thing that interested me most about the letter was that it was real, and simple. I was so caught up in this false intimacy spending so much time online can provide, that this felt so pure. We were looking for two people and their family, simply to return something that belonged to them. I didn’t want to rely on the internet, but rather try to find them the old-fashioned way, by foot, and see where we could go in the city to find information. I wanted that human contact even in the search process, the face-to-face interaction. So, Todd and I began our quest: We went to the municipal archives and scanned census records for my address, their names and any others mentioned in the letter itself. We went to the Greenwich Village Society for Historic Preservation and the New-York Historical Society library and talked to the employees there, but we kept coming up short—nothing led us to the family. After exhausting our in-person options, we went back online. We made a website, www.lostletterproject.com, Todd uploaded the video he’d shot of me, we posted it to all our social media platforms, and we asked for help the same way he had with his found roll of film. I remember watching the engagement happen in real time—people were spreading the story and commenting, it happened so fast!

Receiving a seventy-year-old letter in the mail somehow wasn’t the most astounding part of this experience, but rather how people reacted when they read about my story. A lost love letter made people sit up, engage, want to help. It made them feel something. They excitedly shared our posts, commenting on Twitter, on Facebook, everywhere about the story, “Greenwich Village Woman Receives Letter Sent 70 Years Ago.” I should also note, for the five and a half years I lived in Astoria dreaming about one day living in Greenwich Village, this headline made my life. The story got picked up by various news outlets online and was in the NY Post. My brother and sister-in-law called me—they were in a doctor’s office waiting room and Kelly Ripa was holding the article from the NY Post, talking about my letter on Live with Kelly and Michael. Kelly didn’t know me at the time (I was just a Greenwich Village woman!); this was before Kelly was on Broad City, before Broad City was on TV. She just found it fascinating, a true New York story.

Random strangers were curious enough to band together and help me deliver this letter. My romanticized idea of snail mail as this time-honored, tangible form of correspondence was put on pause—the internet can be kind, loving, and intimate too—we had found the family! The letter had been lost somewhere inside the US Postal Service, or floating around the country, behind countertops or hidden under a pile of paperwork for almost seventy years, and the internet found its rightful owners, in forty-eight hours! That’s pretty inspiring. The end of the story doesn’t quite match the beginning, but it wouldn’t have left as lasting an impression on me if it had. Some of the best experiences don’t end with a bang, but rather a dose of reality.

I didn’t end up delivering the letter to an adorable old couple who invited us in for breakfast—no toast or jam—no telling us about their lovely relationship or what it was like to fall in love in my apartment on MacDougal Street. My heart didn’t melt, seeing them together, holding hands after seventy years in their quaint but beautifully decorated apartment filled with Betty’s original oil paintings as we sipped some rare tea they’d gotten years ago on vacation in India (my imagination really ran wild). There were none of those perfect, ribbon-wrapped images of what I imagined might happen.

I didn’t deliver the letter to Joseph or Betty (they both had passed), but instead to their son, Scott, and his half sister Marna. Scott lived on the Upper West Side in Manhattan, only a subway ride away from my apartment, so not the travel-around-the-world-to-deliver-a-letter type of adventure I had hoped for. When I sat down with Scott and Marna, I finally heard their actual story: Joseph and Betty had gotten divorced a little over a year after Scott was born, leaving Joseph a single dad. Scott didn’t have a relationship with his mom growing up, and only reconnected with her much later in life. This love story I’d been fantasizing about couldn’t have been farther from the actual events. But the letter I delivered did give Scott an intimate look into his parents’ brief love for one another when it was real. Neither Scott nor Marna had ever seen this side of their father, his delicate writing, his use of the word God, his soft side. It wasn’t what I’d hoped for, but maybe it was something they’d needed.

Through whatever bizarre twist of fate, and postal service mishaps, I had ended up with a seventy-year-old letter on my kitchen counter, and I’d concocted a story. I wanted so badly to see real love play out, a story of two people that began right there in my apartment. But things don’t usually unfold so gracefully: love, adventures, and in many cases, mail. We grow and change over time, just like our rapidly expanding ways of correspondence. We fuck up just like the post office. We idealize the past, fantasize about the future, and cross our fingers but more often than not, we get a punch in the gut. 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. Nothing is for sure, but it’s all worth it, all the love lost and all the lost letters.


I had never been in love before.



  • "Poignant, funny, and beautifully unabashed, I Might Regret This takes readers on both a cross-the-country adventure and a deep dive into Abbi Jacobson's gigantic heart."—Cheryl Strayed
  • "As a passionate fan of Abbi Jacobson's comedy, it was no surprise to me that this book is hilarious, peculiar, and very smart. But I was unprepared for the courage she shows in making herself vulnerable on these pages: Jacobson cracks herself open and explores love and loneliness, travel and independence, success and self-loathing. I wish I hadn't finished reading this...I miss her already."—Ariel Levy, New York Times bestselling author of The Rules Do Not Apply
  • "Intimate and brave in a way her audience has yet to experience, I Might Regret This is a funny, vulnerable, generous, and excruciatingly honest look at the beautiful heart that beats inside Abbi Jacobson."—Samantha Irby, New York Times bestselling author of We Are Never Meeting in Real Life and Meaty
  • "Anyone who has had their heart broken will recognize the emotional contours of Abbi Jacobson's post-breakup cross-country road trip...A sweetly wistful collection which includes her hand-drawn illustrations."—Washington Post
  • "Jacobson was seeking to establish a 'small, meaningful connection with a stranger,' and that's exactly what she did. And that is exactly what she's done here, with each one of her readers."—The New York Times Book Review
  • "A truly exceptional memoir...Jacobson is tuned into the ways that physical objects, details, smells and tastes shape the bigger things in our lives. Our loves, our insecurities, our heartbreaks, our griefs: She understands that these things are intricately constructed, that their incongruities and moments of humor lend them texture and weight. The ability to understand that sadness and joy and ridiculousness are necessarily intertwined: This is what has always made Jacobson's comedy so tenderly funny. Like "Broad City," I Might Regret This is in a league of its own."—Michigan Daily
  • "While asking many questions about adulthood--like what the impact of tucking in her shirt has had on her life--Abbi Jacobson infuses her sharp and witty voice to tell stories about loss, love and finding yourself."—TIME.com
  • "Part travelogue, part diary, you come for the delightful observations about road snacks and the life-changing magic of tucking in your shirt, and stay for the endearingly honest, quirky reflections on life, love, art, and work."—Queerty

On Sale
Oct 30, 2018
Page Count
320 pages

Abbi Jacobson

About the Author

Abbi Jacobson is one of the series creators, executive producers, and stars of Comedy Central’s critically acclaimed hit show Broad City. She is the New York Times bestselling author of the illustrated book Carry This Book, and has also created two coloring books: Color This Book: New York City and Color This Book: San Francisco. She is the host of A Piece of Work, the Webby Award-winning podcast from the Museum of Modern Art and WNYC Studios.

Learn more about this author