Images courtesy of Josh Gondelman / Plume
When we heard about You Blew It! (Plume), we knew we had to reach out to Josh Gondelman and his writing partner Joe Berkowitz—and not just because the subtitle is An Awkward Look at the Many Ways in Which You’ve Already Ruined Your Life, which sounds more than just a little useful at the moment. Josh sharpened his comedic knives in Boston before moving to New York, and in addition to writing for the brilliant “Last Week Tonight with John Oliver,” continues to be one of standup comedy’s enduring clever wits. With their new project on shelves this week and a reading at the Brookline Booksmith, we asked Gondelman and Berkowitz, the latter of whom is also a writer for Fast Company, about shit we thought not many other interviewers would ask …
The book is written with a comic’s self-deprecation, but also with some confidence, almost like a popular wiseass in middle school might have. Are you more bashful, or do you walk with some respectable cockiness when you’re not writing (or on stage) as well?
JB: Josh can better speak to the comic’s perspective on this, but for me, I tend to write with more confidence than when I talk—even if it’s about material that makes me seem completely devoid of confidence. The reason is because when I talk I tend to either ramble or say the kind of things I can’t walk back, but when I write I can just keep refining until it’s not embarrassing. Or less so, anyway.
JG: Ha! I’m definitely not bashful, but I wouldn’t say I’m cocky either. My day to day vibe I would categorize as “aggressively polite” or like “self-assured twerp.”
There’s a lot of observation in here, almost like a field guide, and a lot of it is clearly based on your own experiences, though not specifically referenced herein (with exceptions, sure, but in general). Why is that, and more importantly, what’s your most insane or disgusting personal roommate story since the college anecdote that you note in the book?
JB: We didn’t really want to give much indication of who the real people depicted in this book are, lest they read it or anyone who knows them does. So that’s why we kept the stories to a minimum and mainly used hypothetical examples. Also, we wanted the book to be more universal rather than just “here are some dumb things that happened to us because we’re dummies”—although some of that obviously made it in. Most insane personal roommate story for me would probably be the Disney animator I lived with—I went to college in Florida—who would hang up sexually suggestive, anthropomorphic images of beloved cartoon characters every chance he got.
JG: We definitely tried to protect the innocent and avoid the wrath of the guilty by gently obscuring names and identities. I’d say the grimiest roommate situation I’ve had was living with like seven guys in a house in Allston. There is not a residence that exists with enough bathrooms for seven 22-year-olds. Plus, we’d hold off on turning on the heat until the last possible moment, so for most of October I’d sleep in a hoodie and winter hat like Bill Belichick on the sidelines.
How do you know about things like work parties, you know, being a comedian and all? Did you have to step out of your element for this one at all so that it could be relevant to someone who’s not in show businesses? (BTW, the party tips are phenomenal).
JB: Between the two of us, we’ve been to a fairly wide variety of parties. I feel like this question suggests we’re not cool enough to go to that many parties, which is simply not the case. Just the other day we were at a party and it ruled. If you enter ‘Party City’ on GPS, it doesn’t take you to that store with the pinatas and kazoos—it just GoogleMaps the way to my pants.
JG: I used to teach pre-school, and I had work parties then! There were some that were at school for all the families and then others for just the staff. Pre-school teachers get after it when they’re off the clock. It’s intense. Plus I’ve done a lot of work parties at girlfriends’ offices, which can be the nexuses of various forms of party discomfort.
You mention that couples shouldn’t sit next to one another in a booth. I agree. But in passing moments like this, you don’t seem to hold a grudge against such perverse creatures. How much of the stuff in your book relates to pet peeves? And do you sweat the small stuff?
JB: We tried to limit personal preference as much as possible, again to try to get at more of the things that are maybe universally despised but unsung. It was difficult at times, because we are two people and we don’t agree on everything. For instance, one of the authors is fervently anti-brunch, and the other is NOT a monster. As for sweating the small stuff: yes. It feels unavoidable if you’re the type that over-thinks things. Nothing matters but everything’s a stress.
JG: So much of the book is about peeves, but less pet than public. We tried to stay away from things like: “Everyone knows cilantro tastes like soap, right?” We stuck to things that are either widely considered garbage or we think should be widely despised. There are a lot of actually horrible things in the world, but we chose to wrote about how even when things are good, they’re like … moments away from feeling like they’re terrible. Even on your best day, everything can fall apart if two people are making out really hard on the stoop to your apartment building. Who are they? Why do they deserve that? Don’t they know you have Bob’s Burgers on DVR to watch?
I hate to ask about process, since it’s nerdy, but this is a real, actual book, with some substance to it, as opposed to, say, Richard Lewis’ latest, which I love, but is about 150 words in total. How do you stockpile this stuff? Refine? You go to a log cabin? Do you write drunk? Stoned? Backstage?
JB: We both had a few ideas kicking around when we started the book, but from the time we were shopping it around through a day or two after we got the deal, we were really making as much of an effort as possible to take in all the angles of situations we got into and mine them for everyday awkwardness. After that, we were able to sort of diagram out everything we wanted to cover, some sections in greater detail than others. And from there, it’s just that the few weeks we’re working on the Friends chapter, you pay a little closer attention to how you interact with your friends—what they do that annoys you, but mainly, and way more importantly, what you do to annoy them.
JG: I’m always happy to talk about nerdy process stuff. We would meet up, usually at a bar, and outline chapters. Then we’d break up assignments. We’d email each other to ask for extensions on the deadlines we wrote for ourselves. My actual writing, I did lying down on my couch like a Victorian handmaid who had fainted from exhaustion. I don’t drink and write, but I need an iced coffee at least as a reminder that I’d at least intended to be productive. Eventually we’d actually send each other some work, edit over email, and then meet up again to do some more outlining and question whether anything we did was any good and why we bothered even trying.
BONUS: Some of our favorite moments from You Blew It! …
On Handshakes …
What was once a simple clenching of fingers for the purpose of making sure the other person wasn’t going to stab you with a sword is now a minefield of unregulated finger gymnastics.
On Family …
A family reunion is, at the most basic level, a celebration of an entire group of people who, over the course of generations, did not let anyone get eaten by wolves. (If someone had, they certainly would not be welcome at Aunt Linda’s place on the Cape.)
On Tinder …
Online dating is a smorgasbord of snap judgments and no second chances. The quicker you eliminate individuals as potential love connections, the quicker three nearly identical people emerge to take their place like sexy whack-a-mole. As the automatic dismissals pile up, revealing that you do in fact have a “type,” you begin to refine whom you really are interested in. Some of these folks will be fast- tracked into the messaging stage because of sheer hotness, but for everyone else, a profile that doesn’t suck is how you level up.
On Roommates …
People can start almost anywhere on the stranger- to- friend spectrum of roommates, but unlike young couples living together, there’s no chance of these relationships blossoming into something more. Friends will not become best friends, and barely tolerated Craigslisters won’t become buddies. The best that most of us can hope for is just coming out on the other side free of litigation and future blackmail attempts. Beyond dirty dishes and late rent, roommates must often deal with plenty of other quietly crushing situations that even Steve Jobs couldn’t help to prevent. Or maybe he could’ve! That’s something we’ll never know. Because Walter Isaacson is very bad at his job.
On “Unimprovement” …
Telling someone he “cleans up nicely” means the rest of the calendar year he dresses like a Dickensian chimney sweep. If you’re too emphatic about how great your friend looks now, he gets embarrassed about how he looked before— like when you go see your barber and he gives you a look that says, “How have you even been walking around like this?”
On Your mom’s Facebook page …
If you thought getting chain e-mails full of urban legends with subject lines like: “Fw: Fw: Fw: Fw: Fw: Fw: Obamascare” was annoying, it turns out that’s just the beginning. A parent who runs amok on social media can complicate/worsen your life in many different ways. Regardless of one’s age, level of physical fitness, and gender identity, a parent leaving the comment “gorgeous” or, even worse, “hawt” on any and/or every Facebook/Instagram picture is an incredibly effective cock block (or, for women, a “vajector seat”).
On Nerdery …
The term “nerd” has lost all meaning. Not because nerds have become cool. (They have not. If anything, they’ve become even nerdier than previous generations of nerds could calculate.) It’s that everyone has become a nerd about something at a time when technology and brands have turned public obsessing into a national pastime.