BK: That’s what I wanted. To me, the hard thing to do here is to not have it be something that was sappy or treacle or feel-good, but also not be something that was just cold and clinical and funny, but had no soul. So the challenge was, how do you have it be funny and have people be laughing, but also, when they finish an essay or finish a piece — not necessarily every time — but [they] feel like, “Oh, wow, I just got a little window into that person’s life or that experience,” or “Yeah, I felt that way”? … That’s what we tried to do on The Daily Show, really, is kind of connect to what people care about, but not be over the top in terms of [being] so broad that there’s no substance to the humor, or so serious that there’s no humor.
OW: Was there a lot of editing, then, because of that, with some people? Did they go too far over the edge?
BK: No. … The hardest part about it from an editing standpoint was just reminding people that in some way the pieces had to be lessons. … There had to be some kind of takeaway that the author, either ironically or seriously, learned from this experience. … All I cared about was that it was something real and that, when you finished reading the piece, you felt that that was a true enough experience.
OW: When I first heard about the book, I thought, “Oh, this is going to be a ‘guy’ book.” But from when I read the opening essay, it really seemed to suggest that women have a lot to learn, too, and as a female reader, I got a lot more out of it than I had anticipated.
BK: The goal was to write a book from the male point of view that has — I don’t know whether you’d call it male humor — but just … is written by male humorists that, at the same time, does provide some kind of window into men’s processes and how they respond to things that would be interesting or informative for a curious woman.