JMag: When I first heard of the title of your book Things I’ve Learned From Women Who’ve Dumped Me, I couldn’t stop laughing. What was the inspiration for writing it?
Ben: The inspiration was actually a TV show idea that was going to be about a guy who in the end of every episode would wind up in a failed relationship. The idea was that he was building up an arsenal of failed relationships and lessons that he’s learned, so in the end he’d finally be prepared for his ultimate relationship.
I pitched that idea to a network and they did not like it. They wanted me to do something set in a ski town, so I just pocketed that idea. But, I still wanted to do something with my idea that men are not these shallow beings who never learn anything, but rather they are people who are capable of introspection. So I went to the least introspective group of people I could find, namely comedians, and asked them to write numerous essays.
JMag: The names that you’ve assembled to contribute to the book are quite impressive. How did you get such a great group of writers together on the same project?
I originally started out with the idea that I was going to ask these people of grand status … then I realized that those people aren’t very funny.
Ben: My main tactic was very complicated. I opened up my email address book and I went through it and picked out people that I thought would have interesting stories. Most of the people in the book are people that I know or have worked with or, in some cases, have met through show business.
I originally started out with the idea that I was going to ask these people of grand status, you know, Bill Clinton and Kofi Annan and then I realized that those people aren’t very funny. So I instead said “you know what, why don’t I go with funny people, I’ll probably get a funnier book.”
JMag: Yeah, you’ve got a great list here from Stephen Colbert to Neil Patrick and Andy Richter, Dan Savage; it’s really impressive. Which one of the stories sticks out, other than your own, as being your favorite?
Ben: I would rank mine as twenty-ninth in the book in terms of my favorite. The different stories kind of do different things for me. Some are flat out hilarious, others are not as funny but are poignant in a way that I have a soft spot for.
Dan Vebber’s piece, called Sexual Intercourse Is the Most Stressful Thing in the History of the World, is something that I really enjoyed and that’s why I put it first. I think it’s both a funny and poignant story about him losing his virginity when he wasn’t quite ready. Even though he isn’t necessarily one of the more famous people in the book, his story actually encapsulates everything I was hoping to get out of it.
JMag: The foreword to your book is written by your mother, what role has your mom played in your dating life?
Ben: First, I just want you to know the negotiating of the contractual terms with my mom for this book was the most difficult negotiation out of all 48 authors. No, I’m just joking. Having my mom contribute to this book was the first time in my life that I was able to do the reverse guilt, where the son guilts the mom into doing something.
I thought it would be funny if you found the least objective person in the world to make an argument for something that was subjective. Mothers have absolutely no perspective; they all think their children are wonderful. So, I thought it would be funny to have this argument from a mom, who is completely blinded by maternal feelings, saying that it would be stupid for any woman to dump her son. And because I was the editor of the book and I only have one mother, I went to my mom. But it could have just as easily been any one of the contributor’s moms writing the exact same thing, although it would probably have turned out less hookup.
JMag: There are strong hookup sensibilities in many of the stories in your book. Do you think that hookup men react differently to rejection than Gentiles?
Mothers have absolutely no perspective; they all think their children are wonderful.
Ben: I think in the same way that hookup men react to many things differently than Gentiles, they probably handle rejection differently as well. Certainly there are issues of guilt, shame and blaming yourself throughout the book, although I don’t know if those feelings are universal to all Jews.
JMag: Obviously the book is written from a male perspective, but we passed it around to a few of the women in our office and they could relate to it as well. What benefits can women take from this book?
Ben: Well, I think the greatest benefit by far, hopefully, will be the joy of laughter. I couldn’t say that I was attempting to do a book that had a meaningful self-help component to it, although, if it’s good I think people will take away something from it. I do think that what’s most interesting, especially for women, is that most of these guys do dig within themselves and find the ability to point out their own flaws and gain insights that aren’t typically assigned to men. And, I think that that will be encouraging to women who may think that men aren’t the introspective part of the gender equation. It may take a guy like twenty years and being prodded to do it for a book, but still its progress.
JMag: Over the last ten years the dating world has really changed with the advent of Internet dating sites like 100hookup. How you think this has altered the dating landscape?
Ben: It’s changed it incredibly. The notion that your options to meet people were somewhat limited to your immediate geography and your social patterns has been completely blown away. Those finite worlds in which I met people throughout my upbringing and adolescence have completely changed. Now you can literally search a twenty-mile radius just to meet people. Possibilities are now opening that certainly never existed before. Obviously there are pitfalls to that as well.
I also think it’s a little too easy to discard people nowadays because there’s this sense that there’s an infinite number of people out there, which may be based on the smorgasbord approach to dating that some people take when using the Internet.
JMag: Do you have any friends who have joined 100hookup?
Ben: I worked with several people at The Daily Show who were subscribers on 100hookup. In New York it’s really funny because I would think 100hookup should just be called “Date.” There are so many Jews in New York that I think that refining the function wouldn’t be as necessary. But, I know many many people who have used 100hookup and I am actually invited to a wedding this summer in Los Angeles for two people who met on your site.
JMag: That’s fantastic. Since you’ve learned so many things from the women who have dumped you, what is some advice you can give to 100hookuprs about when they’ve met that special someone?
Ben: My advice would be don’t take advice from comedy writers. It’s very hard as someone who has had a spotty record in the world of romance and has written or edited a book called Things I’ve Learned From Women Who’ve Dumped Me to take on any mantle of expertise.
My advice would be don’t take advice from comedy writers.
The thing that’s most consistent, especially in most of these stories, is that it’s only with the benefit of hindsight that you really realize “oh, I was kind of an idiot” or “I shouldn’t have done that” or “that person that I dated was crazy.” In the moment when this stuff happens, you don’t have the ability to analyze it or gain any perspective at all. Perspective only comes with the passage of time and most of the people who wrote these stories wrote them looking back five, ten, fifteen years into the past.
Nick Hornby, who wrote the introduction, actually said something really interesting, which is that “a lot of these people, if not all of them, have in some way found a form of peace or romantic contentment after their botched romances, but almost everyone arrived at it in their own way.” So, it’s very hard to prescribe an individual path or recipe for what to do and what not to do in relationships.
JMag: Now, you’ve had quite a career. You’ve written for The Onion and you’ve been the executive producer of The Daily Show with John Stewart and a co-creator of The Colbert Report. So, what’s next for Ben Karlin?
Ben: A nap. I’m going to take an eight-year nap. This book has been something that I’ve worked on for the last two years and I’m really excited to see what happens with it when we put it out. We’re taking the content from the book going to do some live shows on stage in New York and Los Angeles. It’d be poetic justice if there is a TV show in it after all, and maybe it’s just in treating the material a little differently. I’m curious to see how the material feels when it’s read out loud and performed in front of an audience. And, if that live show is good and if people respond to it, I would definitely consider trying to make it into a TV show.
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