From: Ben Karlin
To: Elizabeth Wurtzel

I’m not sure you are going to get your handbag this way. Go for it! Just put it out there that you want one. Why beat around the bush?

Everything I want is vague and ill-defined. That goes for life goals too. I have no ability whatsoever to look into the future and conjure a picture of what my life will be – or even what I want it to be. Please read this in as un-angsty voice as possible. It does not make me nervous. Just a bitch to shop for.

I am working on a bunch of crap for HBO. Though that is not how I pitched it to them. I presented it in a manner that would make them think it is going to be quite good. I am writing a pilot about the world’s 237th richest man. We have another show, written by someone else, about a UFO alien death cult set in northern Wisconsin, and a third, loosely based on my book, which is a comedy-variety show built around the theme of failed relationships. As much as I loved working on a daily show, there is something about the promise and possibility of developing multiple ideas that thrills me more. Like, even though I ground myself down to a nub running multiple shows, the idea of having multiple shows is still thrilling. This inability to learn from past experience could be labeled either “boundless enthusiasm” or “fatal flaw.”

I really don’t want to get into a New York neighborhood apologia. In the 9 years I have been here I have lived in the West Village, Hell’s Kitchen, Greenpoint, Greenwich Village proper, off the Bowery in Noho, Clinton Hill and Fort Greene. What does that say about me other than settle the fuck down? There were things I loved about each place, though I loved Hell’s Kitchen least. Right now, I do live in Brooklyn, ambivalently. Don’t hate me for it. Hate me for a number of other reasons, which I would be more than happy to elucidate herein.

I am not now, nor have I ever been a birkenstock wearer. Here, however, for the purposes of partial disclosure, are some things I have worn or done that embarrass me in retrospect, though I stop short of regret:

1. Wore an earring briefly in high school, and again in college
   
2. Goatee for about a week, also in college
   
3. Wore a bandana in that hippee-helmet kind of way, though at a summer camp, which makes it slightly less obnoxious.
   
4. Frequently wore white tube socks with sneakers and shorts while not engaging in athletic activity
   
5. Killed a man just to watch him die

One of those things actually does not embarrass me.

Next: What the memoirist and the comedy writer have in common

Life lessons: Things I've Learned from Women Who've Dumped Me Not long ago, Ben Karlin quit his job as producer of The Colbert Report to edit a book of confessional essays about breaking up, Things I’ve Learned from Women Who’ve Dumped Me. Karlin began his career at The Onion and worked at The Daily Show before helping to launch Colbert. He was used to occupying a position behind the scenes, riffing on current events and the world around him. But confessional writing reverses those polarities. Suddenly his job was to direct the jokes inward—to wring comedy out of his own life, and encourage a bunch of other writers to do the same.

Elizabeth Wurtzel knows a thing or two about confessional writing. Her 1995 memoir, Prozac Nation, took an almost masochistically candid look at her experiences with depression. It made her a household name, equally beloved and reviled. She published several more books and then, inspired by the chaos that immediately followed 9/11, applied to law school at Yale, where she’s currently finishing up her thesis.

We thought Wurtzel probably needed a distraction, so we sent her a copy of Things I’ve Learned from Women Who’ve Dumped Me and set her up in an e-mail conversation with Karlin, who now heads a production company called Superego. To say it got confessional quickly is the understatement of the year. If you’ve ever wondered what Elizabeth Wurtzel’s dog looks like, read on.

From: Elizabeth Wurtzel
To: Ben Karlin

Why superego? Why not id?

From: Ben Karlin
To: Elizabeth Wurtzel

Well, the id comes up with the better ideas but is pretty shitty at getting things done.

From: Elizabeth Wurtzel
To: Ben Karlin

Getting things done is so overrated! For every brilliant idea, there are a million shitty executions. Have you been to the movies lately?

Sorry...this is not what we're supposed to be talking about at all! I think we're meant to talk about dating, another nice concept that often fails when acted upon. But I guess that's not news.

How are you? And while I'm asking questions, the author blurb on your book says you live with your family, which would seem to suggest that you have a family to live with. Correct?

We are family: A 1979 Pittsburgh Pirate From: Ben Karlin
To: Elizabeth Wurtzel

First of all, has any one pointed out how odd it is to have a physical address as part of your electronic signature? Is that like saying, “In case this whole revolutionary form of communication that is changing the face of humanity as I type this doesn’t work out, drop me a note”?

Anyway, I do, in fact, live with my family, if wife and child constitute family. I guess that does, though I tend to think of family in more pluralistic terms – like multiple children or at the very least the 1979 Pittsburgh Pirates.

I am winding down all my book stuff, which has mostly been fun and fine, and am back to working on content to put on the TV.

This is like an internet first date. All awkward stops and starts and I am already convinced it is going terribly. Like me! Why won’t you like me!

From: Elizabeth Wurtzel
To: Ben Karlin

Yes, it is odd to have one's physical address attached to an email. They tell you to do that, though. Don't know why. I guess if you're a girl there's always the secret hope that someone might send flowers or something even better, like diamonds. Or a Birkin bag. Or a really good vacuum cleaner. Or, in my case, I could use a new sofa.

Gossip girl: You never know when a third party might be listening I could go on.

But enough small talk.

Let's start our second date.

And truly, since you are married and I'm not, it's more like an affair. Right?

Do you do that? Have emotional affairs? That seems to be the new thing--to not bother with the whole mess of physical intimacy but just get deeply intellectually or otherwise entangled with a person you're not married to or going out with as a way to relieve the tedium of foreverness. Not that marriage is necessarily tedious. Of course, I'm sure yours isn't...

Forgive me for being so forward. I just don't know anything about the 1979 Pittsburgh Pirates. I know a fair amount about the 1986 Mets. And the Red Sox of that same year. Who could forget the Bill Buckner fumble? Probably not Bill Buckner. My guess is that he still occasionally wakes up screaming over that snafu.

Anyway...

As much as you want me to like you, I want you to like me too--after all I'm Jewish, with all that implies. But I must admit, I have a few vicious tendencies. Like it occurred to me that this is the perfect forum for gossip, because we're having a conversation that's sort of being overheard, so I could say something mean about someone who irritates me and pretend to have forgotten that I was speaking to anyone besides you. Which would be a vicious thing to do, but only sort of.

Girls are so tricky...

Next: Married people have three kinds of affairs. One can't be forgiven.

Last night Jon Stewart and Stephen Colbert returned from their writers' strike-induced hiatus. It was a glorious evening for TV junkies who have steadily lost our will to live over the last couple months. Although Colbert filled (nearly) the entire introduction with applause for himself, it beats reruns, awful reality shows, and going outside to actually interact with other human beings....

Graduating from college sucks. It’s just awful. If you’ve failed to line up a job during your senior year, then commencement marks your transition from scholar to slacker. If you have managed to get your inexperienced ass employed, then it commemorates your shift from scholar to abused underling, since there’s no such thing as a good first job. Even if you’re doing something impressive to parents—med school, say, or i-banking—chances are good that you won’t see sunlight again until your thirtieth birthday. Graduation is that rare ceremony celebrating a change for the worse. Commencement speakers know this, and so usually they organize their speeches around a set of useful fictions. Follow your dreams, they tend to advise. As long as you never stop working at becoming rich, saving the world, and achieving fame, you’ll be happy. Which is why we loved the graduation speech Ben Karlin recently gave at his alma mater, the University of Wisconsin. As the ...