For a writer, Sloane Crosley’s a pretty fancy young lady. For starters, she’s been in the New York Times—for her fashion sense; she’s gone head to head with comedic Scottish bulldog Craig Ferguson and held her own; and she’s been knighted—OK, not yet, but she is the author of two bestselling books of rabidly funny essays, I Was Told There’d Be Cake and How Did You Get This Number, which has a pretty nifty Moby-winning book trailer. And if you don’t already hate her, check out her writing space.
We planned on meeting at a coffee shop in the West Village, but ended up wandering along the banks of the Hudson, where we were promptly swarmed by one too many middle-aged dudes in gold Ed Hardy t-shirts.
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The Rumpus: You’ve written about everything from douchebag ex-boyfriends to cat porn and Portuguese clowns. It’s frightening to think where all this stuff comes from.
Sloane Crosley: It’s a “Where do babies come from?” kind of thing, where I—although wait, that’s actually an unfair analogy. Because that’s an easier question.
Rumpus: “Where babies come from”?
Crosley: Yes, because there’s an answer to that. A singular one. It’s not like, oh, they come from someplace different. Some people get them from the store—Gummy-bear babies—and some people get them from sex, you know? So in a way, that’s the answer to your question about what I write: Gummy bears and sex—because this stuff comes from someplace different every time. Sometimes you have a broad theme in mind, and you hone it in. And sometimes it’s a random funny story you expand upon. I mean, if you told me to write an essay about absolutely anything right now, I’m not sure what I’d write about.
Rumpus: Well, if your first two books are any indication, it’ll probably come from somewhere in your 
autobiographical past, right? As opposed to something about, say, Goethe.
Crosley: That one’s on the docket! But yeah, that’s not exactly true. I just finished writing a piece for Playboy about mohelim, the rabbis who chop the foreskin off the babies, interviewing a ton of them, researching bris culture, figuring out what clamps they use—and that’s certainly not my own life, because I don’t have a penis and it’s never been chopped. But you’re right, I do mine my own life a lot, but then everyone does. You have to have some connection to what you’re writing about, I think. It’s really hard to get away with stream-of-consciousness ruminations about miscellaneous topics without knowing what you’re talking about.
Rumpus: You’ve been attracted to the form of the humorous personal essay, like David Foster Wallace, David Sedaris.
Crosley: David Rakoff. All the Davids. It’s funny, the Jonathans take over fiction and the Davids take over nonfiction. What’s up with that? That would be great if that was your question—why don’t you end every question with “What’s up with that?”
Rumpus: Yeah. OK. What’s up with that—that form, the humorous personal essay?
Crosley: I think it’s what comes out naturally. The interesting thing about the question “why are you writing about what you’re writing about” is— The dirty secret of the answer. That would be that I don’t know. But that doesn’t make for a very interesting interview, does it? People assume that once you have a modicum of success that everything you did up until that point happened on purpose. And that you have the answers. Because you didn’t fuck up. But you do fuck up. I mean, there are essays I wrote that will never see the light of day. There’s a novel I wrote that will never see the light of day. The writing isn’t the problem, hopefully. By now I feel comfortable saying, OK, that’s on purpose, that’s not an accident, X is what I’m doing and Y is not. Meanwhile I try to figure out what I’m actually doing.
Rumpus: You mean your voice—finding your voice?
Crosley: Not really. For me, plot is the hardest thing. Structure is the second hardest. And I feel like that’s true for every aspect of my life. Whenever I move in to a new apartment—if you came to my apartment right now you would think that I’ve lived there for eight years, and in reality I’ve lived there since October. That’s because I like to get all the little details right and then I consider the more practical things. The pictures are all hung just so—I have a power drill, stuff goes into the wall right away. But whoops, I’m sitting on the floor and maybe I should get a sofa. And I write the same way. I move in from the least logical point and figure it out later, and luckily that works very well for humor writing.
Rumpus: My favorite essay in the new book is the last one, “Off the Back of a Truck.”
Crosley: I just started writing this thing. It’s really about two different people, and that was hard, because on the one hand the facts of the case are this one person, but I’d forgotten how that relationship felt—I had no emotion about that. I remember it being bad. I just didn’t remember how it was bad. And one of the first things I wrote in that essay was the line equating the brain to any other organ in the body. If you’re kind and healing to it, it will be kind and healing to you: it’ll do you a solid. But when it came time to writing about what happened, how do you dig up the memories you threw out? I got around that by applying what I felt about a more recent heartbreak—there really have been two big ones—and so that was an extraordinarily difficult essay to write. Imagine taking the two worst romantic slights you’ve had in your life and combining them into this one two-headed monster. Now think about it constantly like your book depends on it. Because it does. It’s a lot like The Incredible Hulk.
Rumpus: Like The Incredible Hulk?
Crosley: OK, not like The Incredible Hulk I don’t know. I mean, I know it’s different than the other essays in that book, but I don’t quite know how. Which is unfortunate because a lot of people seem to have an emotional reaction to it and I wish I could replicate it, but I really don’t know how to provide them with the ingredients. Or give them to myself. Basically, I thought about writing it and because I had this intense aversion to writing about boys, I thought: How do I make it funny and not stupid? And that was where a lot of essays in the second book come from. How do I take something that’s not really funny and make it funny? A bear gets smacked by a car—how do I make that funny? Is it funny? And in “Off the Back of a Truck,” there were two ways. One, this parallel story of the furniture salesman, and, two, the universal story of getting over the breakup. I think it’s really funny, how people get so devastated over breakups and can’t see anything else in their lives. It’s the water boarding torture of the human heart.
Rumpus: Yeah, there’s a sadness in the second book.
Crosley: This is what happens when you write a funny book when you’re a little more than casually depressed, I guess. This is what comes out: Round 2. I think some people are disappointed by this book, to be frank.
Rumpus: What? Why?
Crosley: I think they think it’s not funny enough. It’s like with Saratoga Springs, New York—there’s more bars per square block in that town than anyplace outside, say, New Orleans. And I think that’s what people wanted with the second book—just replace beer with jokes. It’s not like I got bullied into anything. I knew what I was doing eventually. But when people complain that the second book isn’t quite enough like the first, I’m, like, listen people, there’s a line of progression here. It’s not like I gave you a pop album and then produced an album of ukulele music.
Rumpus: You’ve been called the “voice of your generation” and “the lady Larry David”—or was it Larry Charles?
Crosley: Larry David is another David! A hidden David.
Rumpus: But the pressure’s on, you’re supposed to be writing for some generational zeitgeist, right?
Crosley: I didn’t even know I had a generation. There’s a great line from Dazed and Confused: “The 60s were great, the 70s sucked, so the 80s are going to be amazing!” And as a viewer you’re like oh, man, little do you characters know the nostalgia that will develop for the 70s. It’s that whole idea from Midnight in Paris, of not loving the one you’re with. For me, when I get too detailed with my childhood references, I’m just glad that people get it. So I don’t see myself as the voice of my generation, whatever that is. I think it would be unfortunate if that were true, because then I should be saying a hell of a lot more.
Rumpus: Now it’s like The Gossip Girl generation, and nobody seems to be saying anything important about that.
Crosley: Is that our generation as well? God, I hope not. I think I come from the Facts of Life generation. I wasn’t allowed to watch Married With Children or I might have come from the Married With Children generation. But the Facts of Life generation was very floaty and weird, because I just feel like we didn’t have the technology. I very specifically remember—
Rumpus: Before email. We grew up before email.
Crosley: Yes. My senior year of high school, there was this girl named Leah. We were kind of friends in high school. We weren’t great-great friends, but we were both chatty enough to be like “are you on AOL Instant Messenger? I am too!” And I remember typing to her the next day how weird it was that we had this alternative life, this disconnected conversation. Then I went to a small school for college and—I wonder if they still have this—there was a list you could check to see who else was online at six in the morning, and it would only be a few people. We were still learning how to use all that email stuff to inform our romantic relationships. It wasn’t supplementary to human relationships. It was completely separate. Then it went through a phase of being supplementary to human relationships, and now the majority of our relationships with people are online or via text messages. And then after my generation, I don’t know. There were a lot of people named Cindi.
Rumpus: After us?
Crosley: Before us. Sorry. But that’s what I mean, is you and I are in this weird in-between land of hyper-colored shirts and Kudos bars. Do you remember Type 1 versus Type 2 tapes? Those are ours. But a detail like that is so fucking subtle. And I think that’s why nostalgia is such a powerful thing for us. We had so much change so quickly. It was so hard to hold onto a movement or a trend. Then with the web, our actual day-to-day interactions with each other fundamentally changed from the time we were in high school until college. We’re on the line. We didn’t grow up with the Internet and we didn’t grow up without it. [Dude in a gold Ed Hardy t-shirt walks past.] See, that’s not us. That’s someone else’s generation. The D-bag Generation. Oh, which is also something we didn’t have. We didn’t have the term “douche.” Or we did, but it was literal. It was something you did to yourself.
Rumpus: Now we want nostalgia right away. We want it packaged up, like Twitter or Facebook—we want to record our own history while it’s still happening.
Crosley: Yeah, but that’s just wanting fame. That’s nothing new. But I do think we’re more obsessed with nostalgia because of all this stuff. Honestly, if whatever you want to do with your life is ingrained in your personality enough, the latest technological fad is not going to affect it. Not at all. If you feel that being on Twitter is going to encroach upon what you’re going to write, then whatever you’re writing is probably pretty weak and not of huge value. I believe in distraction. I’m distracted right now but it’s not the Internet’s fault. It’s like saying looking at real-estate porn all day is affecting my ability to be an architect. I mean, it’s distracting as hell, but so are a lot of things. TV is distracting, living in New York is distracting, flowers are distracting. Look at the birdie out my window. I didn’t have the Internet at home for a long time, but now I do. And it’s really distracting and sometimes I want to punch it but my computer was really expensive.
Rumpus: You should pull a Jonathan Franzen and cauterize your Ethernet port.
Crosley: I should totally do that. It’s so funny to me when writers get extremely Spartan. I was talking to a writer I worked with once who said she was so disgusted by her own TV-watching that she unplugged the TV, wrapped the power cord around it and threw it in the closet. I mean, don’t be so dramatic about it. Just turn it off. Also the Internet can be a good thing. Sometimes you’re working on something that calls for a Google search.
Rumpus: As long as you don’t spend all day Googling yourself.
Crosley: I guess that’s better than spending all day douching yourself. Or is it the same thing? How does a douche work anyway? Clears everything out? I should Google that.
