Raphael Bob-Waksberg Will Break Your Heart and Make You Laugh About It

“This book, I will warn you: I can’t read it in public because I will cry.”

That was one of the initial messages my editor sent me about Someone Who Will Love You in All Your Damaged Glory, Raphael Bob-Waksberg’s hilarious, heartbreaking debut short story collection. If you recognize Bob-Waksberg’s name, it could be because he’s the creator and show-runner behind BoJack Horseman, the animated Netflix series about a depressed, self-sabotaging, alcoholic, washed-up horse actor. It could also be because back in 2013, you read a long, fictional, and eventually viral post that someone had written and posted in the Missed Connections section of Craigslist. That was Bob-Waksberg, too. (A version of that original Craigslist post, “Missed Connection – m4w,” is included in this collection).

Someone Who Will Love You in All Your Damaged Glory is a masterful tightrope walk between abject sorrow and genuine hilarity, a book that Bob-Waksberg describes as “an argument with itself.” As a writer, I am struggling to describe it, because I want so badly to avoid the cliche “This book made me laugh AND made me cry!” description.

Maybe it would be better to say that shortly after I started reading the book, I sent my editor a photo of one of the pages with a single line highlighted. The line read: “I would try to tell her, Things will get better, but it came out as: Nothing didn’t get worse.” 

Or maybe it would be better to explain how a day later, I sent her a photo of the final page from a story called “Move Across the Country”; how I was crying on my front porch while I sent it; how all I said to accompany the photo was “motherfucker”; and how all she said back was, “OMG I KNOW.”

Or maybe instead, I will just say … this collection of stories caused me to guffaw AND also … occasioned me … into sobs? 

Or maybe sometimes cliches are okay.

This book will make you laugh and make you cry.

I spoke with Raphael Bob-Waksberg about Someone Who Will Love You in All Your Damaged Glory on the phone, and of course, we started out by talking about what it means to be funny-sad. 

Riane Konc: I feel like you pull off the balance between humor and sadness really, really well, in a way that I envied even before I read the book. I feel like when I’ve tried to sell BoJack to people who haven’t seen it before, what I tend to say is some long speech about how I generally don’t really care for adult cartoons (or just a certain genre of dark comedies), just because I feel like for a lot of them, the quote “comedy” is coming from the idea that: look, these are awful people and they’re miserable, and isn’t that so funny that we put that on TV? And I never feel like with this book, and I don’t feel like that with BoJack. You pull off this balance where awful, horrible, sad things are happening, and that’s not the joke—that’s just things that are happening. But at the same time, super absurd, specific, funny things are happening … because you can’t excise one of those from the others. 

So I’m curious, with BoJack, with the book, just how you handle balancing “I am both of these things, how do I put that into a piece of work?” Is that one of those things you do consciously, trying to draw the humor from the right places and the sadness from the right places, or is that just something that through writing a lot and working a lot, that’s just your style and how it comes out?

Raphael Bob-Waksberg: I think it kind of comes naturally. I think it comes from the work I have done to be the writer that I am. I think that for me, it’s always about who is the character and what does the character want, and what is the hole in the character’s soul—and trying to find that vulnerability and that desire. I think there’s a term in the world of television that a lot of writers don’t like to hear or talk about, which is “likability,” which is sort of a cliche where the studio execs want your characters to be more “likable,” and I actually don’t have a problem with that. I think we do want our characters to be likable, and we want characters that we want to engage with or root for, or we want to root for, or see on television, or read in stories. But I think likability isn’t the same as “good.” We don’t have to like a character who is decent or kind. Sometimes, there are a lot of ways to make a character likable. Sometimes I think it comes more from understanding what that character wants.

RK: That makes a lot of sense.

RB-W: That’s something that audiences or readers can relate to. So trying to find that vulnerability, or help the audience understand what the character wants. Then that helps make the character feel grounded and real and someone that we can root for, despite their flaws.

RK: Yeah, like, you’re an idiot, and you’re making the wrong choices, and I just don’t trust you to make the next right choice, but I want you to, and I think there’s a world where you might! You probably won’t, but you could, and I really hope that you will. And it’s going to break my heart when you don’t.

RB-W: Right. And I also understand why you’re making the bad choice. You’re not just making them to heighten the drama in the scene, although perhaps the scene behind the scene behind the scene shows exactly why you’re doing it. But in the scene itself, it’s explained to me in a way that I understand what you’re doing, and it makes sense. It doesn’t feel manipulative.

RK: There’s obviously quite a range in the book: it’s not a book where you’re just delivering story after story about like, “love wins, and hope is great, and it always will be fine”; but it’s also not like, “ever trusting or loving someone is the stupidest thing you could ever do and it will never work well and it will never even feel temporarily good.” There’s quite a spectrum in there.

RB-W: I think the book is kind of an argument with itself. I think that’s something I didn’t realize until I was done writing it. I feel like the through-line of the book, if there is one, is this idea is that love is a challenge, and love is difficult, and love is scary, and the question that the book posits is, “Is it worth it?” And I think there are parts of the book that are strongly pro, and parts of the book that argue strongly con. And I think if the book is working, then you make your own decision when you get to the end of it, which is how do you feel? And I actually think it’s more about you and where you are in your life and your experiences than the book. But I think the book will hopefully help you perhaps articulate your own argument to yourself, or reflect on experiences you’ve had or how you feel about things

RK: I feel like often have the experience of … I stumble upon realizing what I think about something or what I believe about something through the act of writing about it. It’ll be finished and I’ll be like, “Oh gosh, I didn’t know that was actually kind of what I believed, but … I guess it is.” Did you have that experience with this book?

RB-W: You know, even that succinct summary of what the book is kind of came to me in the last few weeks as I’ve been doing interviews and going on my book tour and talking about the book. Only then have I really been able to articulate what the book is. So it wasn’t really until it was in front of me, as I was writing, that I kind of found that. You know, as I was writing, I would feel like some of these stories make sense for this book, other stories are not quite right for this book. And I didn’t really know why until I got to the end and realized, “Oh, this is what I was doing.” Or even the ordering of the stories and how they juxtapose against each other: you know, stuff like that was more by feel than by anything else. But now looking back, I kind of understand what it was I was building.

RK: Yeah, I was thinking about the way that you organized the stories. One thing I really appreciated about the experience of reading it was, I would—because a lot of them, you don’t necessarily know if this is going to be a happy one or a sad one at the beginning, but some of them you can tell, there’s a different tone. But even when I was near done with one that, by all indications, was a hopeful one, and I should have been feeling vaguely hopeful the whole time, I was still kind of off-kilter from the last story I read, where my heart was just broken. So I was like, “Should I trust that this story is going to give me the ending I anticipate?” But I just couldn’t accept it until it happened, and then it happened, and it was a lovely experience. Like, oh thank God, that’s what I thought was going to happen, but I couldn’t accept that. That sort of felt purposeful.

RB-W: Well, what a great metaphor for love itself!

RK: Exactly. It felt like that.

RB-W: When you’re starting a new relationship, you don’t know what it’s going to be, and it might feel hopeful, but there’s something in the back of your head going “Well, it’s felt hopeful before, and I was destroyed, so we’ll see how this one goes.”

RK: With pieces like “The Serial Monogamist’s Guide to Important New York City Landmarks,” and there were a couple of others, they felt to me like in a different context or written by a different person, it could be a piece that you’d see in Shouts & Murmurs, where it’s more just conceptual and funny. It feels like you took that base and then put more of a narrative in it. Did you have any pieces that kind of started as “This is just a concept, and I’m riffing on it, and now I’m going to go back and give it a narrative”?

RB-W: You know, it’s funny you say that, because “Rules for Taboo” I actually submitted to Shouts & Murmurs. 

RK: But despite its evident merit …

RB-W: Yeah, they disagreed with your assessment. They felt very strongly that this was not Shouts & Murmurs material. Which I certainly understand. I think maybe that what you said earlier: that perhaps there was a little too much narrative sadness in there. You know, it wasn’t quite as light and fun as a Shouts & Murmurs should be. I couldn’t help myself! I couldn’t write the Shouts & Murmurs version, I had to write the melancholy, prickly version.

RK: I love that. Because I read Shouts & Murmurs-esque pieces and write them all day long, which is fun. But I loved seeing what feels like that base structure of you “take this concept, this familiar thing, and riff on it,” but you rarely get to see it with a sad narrative pushing it along. 

RB-W: Right, apparently the editors of Shouts & Murmurs don’t like that.

RK: They just don’t want stories! They don’t want to be sad! That’s not what they need right now.

RB-W: Right, they say, “You can murmur this one, but don’t shout it.”

RK: I was reading in the acknowledgements, in the back where you said something about meeting your wife. You said something about how if you lined up all of these stories chronologically, that you’d be able to pinpoint the moment that you two fell in love. Is there an actual story you were kind of working on around that time? Does that piece actually exist?

RB-W: No, I don’t think so.

RK: Just more the idea of it.

RB-W: I think you would be able to see the gradual shift in my writing where I become a little less cynical, a little more hopeful about the idea of love. I think the later stories that I wrote—not necessarily the later ones in the collection, but the later ones chronologically—I think are a little more hopeful than the ones that I wrote in my 20s when I was very cynical about love and what it meant to be a part of a couple. Or, you know, not.

RK: After that shift, when you were then an In Love Person and not an angry, cynical 20-something-year-old person, did you feel like, “Oh, this batch of stories that I have, these don’t work anymore. I don’t actually believe these,” or was it more like, “I’m not in this place, but these are still true at some point in time”?

RB-W: I’d say the latter, exactly. I felt like, “Oh, I don’t know if I can write some of these stories the way i’ve written them then. But I like that they exist.” And in re-reading them, I think they are compelling and interesting, and again, I kind of like the ping-pong match that’s kind of set up. I don’t want to overstate the idea that these are two different guys who wrote these stories, because they’re definitely not. Some of the later ones are more melancholy or cynical as well; it’s just not quite in the same way, or coming from the same place.

RK: It doesn’t feel like I’m reading a Jekyll-Hyde situation, or even a Will Grayson, Will Grayson situation. Like, one person has written this book, and I don’t think it feels dichotomous.

RB-W: Even at my most cynical, I was a little sentimental, and even at my most sentimental, I’m still a little cynical.

RK: I think that’s why the sad stories and the hopeful ones resonate really well, because they don’t feel like … I am just reading a story by someone who is just tunnel visioned either in hope and love or despondency. I feel like it makes the sadness and the hopefulness—when it comes through—I buy it a lot more.

RB-W: It’s kind of a crapshoot every time.

RK: I notice, when I’m writing, especially with humor pieces, I start because I have the punchline or I have the final image or the final sentence, and I have to work my way backwards to create the rest of the story to come up to it. And sometimes I just write from the beginning like a forward-facing person. Do you tend towards one method or the other? Are there any of these stories where you had a joke or a line or an image, and were like, “Oh, I have to create a story to get to this place”?

RB-W: Rarely. I kind of jump around all over the place, but usually my first way in is kind of the gimmick or the world or the voice of the story. So I’ll be like walking my dog, and I’ll be thinking, “What is this guy thinking right now?” and I’ll start putting sentences together in my head. Or I’ll come up with the format of “What if a party game’s instructional booklet could tell a little story, and was passive aggressive about it?” So I’ll kind of come up with a format first, or the gag of the bit, and then the next task is “Okay, what is this story really about?” 

I like to think that every story I write has kind of two hooks to it. The first hook is kind of like, the fun realization … this is a game. “This woman is doing an impression of a play.” And then the second hook is kind of what is the emotional grounding, what is the thing that makes you go, “Oh, this is about people, this is about a relationship, this is about something.” And so I usually find that first hook first, and then I have to figure out what’s the second hook that justifies this format that I’ve chosen.

RK: I think that’s really highlighting the difference with the format-first structure of doing things. For what I do, I get to cut off what I’m doing really quickly at the joke. It’s like, “Alright, we got the structure, you guys are going to figure out the game, this is super fun.” But then you take it to the next level, like, “Okay, who here died of a drug overdose?” That’s the second game. I feel like that’s difficult. To make it believable, to be able to make jokes shitting on theater people that are super funny, and also real life that’s happening at the same time. Because no matter who in your life has died, or dumped you, or whatever horrible thing has happened … theater people are still easy to make fun of. I feel like that’s important.

RB-W: Right. And sometimes the pain of your grief will make you lash out even more. 

RK: Yes. At deserving crowds.

RB-W: They know what they did.

RK: Last thing: is there anything you’ve been wanting to say about this book, but you haven’t had the chance? Or is there any question that you wish someone would have asked? You can do both sides of the job for this last question.

RB-W: I feel like everything has come up! But I will say: this book is very good. And people don’t always ask me that.

RK: I’m glad you said that. I agree with you!

RB-W: If anyone reading this interview has made it this far, and you’re on the fence about whether or not to buy this book, I would say … do it. 

RK: Wow.

RB-W: I think you should buy it.

RK: That’s really insightful.

RB-W: It makes a great gift. It makes a good, great vacation read. It’s great on airplanes. The audiobook is fantastic. Really, you can’t go wrong. I don’t know that I get to talk about that enough.

RK: Yeah, and just to piggyback off of that: I can see this book being useful on a boat. I can see it being read in a car. I can see it on land. I can just see it in a lot of travel and non-travel situations.

RB-W: Absolutely. You can read it in bed, you can read it on your couch, you can read it on your roof.

RK: If you’re single, you can read it. If you’re happy, you can read it.

RB-W: Just read it! Read it to a friend, read it to an enemy, mail it to a lost love. Get it out there. Get the word out.

RK: Type it line by line to someone you hate. I think that there’s a lot of things you could do with this book.

RB-W:  Yeah, Tweet it. Do what you gotta do.

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