Today's interviewee has recently published a humor book, Maybe Life's Just Not That Into You with Howard Books, an imprint of Simon & Schuster, which parodies the self help genre. His job prior to author was pretty interesting, too: was a staff writer for The Tonight Show with Jay Leno for 14 years. Also I think he looks a little bit like Dexter from "Dexter," no?

How did you get your staff writing job at The Tonight Show?
I was living in my hometown of Omaha around 1990 and Leno was guest hosting for Johnny Carson on Monday nights. Since my grandparents used to live next door to Carson's parents in a small town in Nebraska I'd been viewing The Tonight Show since I was about five, even though I didn't get the jokes.

So I was watching The Tonight Show on a Monday because at the time I didn't have cable. (I've since upgraded and even get premium channels.) And Leno was doing his monologue and I said, "I bet I could write that." And so I wrote some jokes, and sent 'em to Jay care of NBC. He called me about a week later and I started selling freelance jokes to him for 50 bucks apiece. Then about a year before Johnny retired I got on Jay's staff and earned a weekly salary from the network. I held the staff job for 13 years. Basically I was pretty fortunate to be in the right place at the right time. Late night TV jobs are hard to come by, especially if you're not smart enough to get into Harvard.

What was a typical day like for you there?
A lot of newspaper reading. I read six papers a day, seven if you count USA Today. I'd write some jokes, and drop them on Leno's desk. Then I'd watch the taping of the show in the late afternoon to see if any of my jokes made the final cut.

It was loads of fun for about the first nine years. There was a talented comedian named Jimmy Brogan who chose the material that got in the monologue and he did a wonderful job. The guy who took his place wasn't as sharp. When Brogan left in 2001 I think the quality of the humor declined. A lot of jokes flat out died. Of course you don't see that when you watch at home, because they edit out many of the clunkers.

Was it difficult to sell a book that parodies self-help books?
It helped tremendously that my coauthor Martha Bolton has authored dozens of books and many of them were very successful. I think she'd been around long enough that publishers trusted her when she said we had a good concept. I came up with the idea for this one, but without her frankly I doubt it would've sold. I tried to sell another book proposal a couple years ago. I thought it was pretty good and I landed a very good agent, but perhaps because I was not a known commodity in publishing it was rejected. Either that or the book was really lame.

What inspired Maybe Life's Just Not Into You?
I was reading through some self improvement books in a bookstore. I think it was a Tony Robbins' book that really sparked the idea for Maybe Life's Just Not That Into You I thought the Robbins' book was sort of pandering, although I realize for the right person that kind of advice does work.

Then I picked up some silly little book that posed "Nothing But Questions." Questions like, "If you could be a bug, what kind of bug would you be?" and that was the entire book. "Do you like your ears? If you could change your name to Fred, would you?" Just these inane little questions. And that was supposed to help you improve your life. I don't want questions from my self help books, I want answers.

I think the original idea was strong enough that the writing went smoothly. This is the first thing I've written that made me laugh out loud while we were writing it.

What's it like sharing the writing duties of a book? Any advice on how to make the process run smoothly?
It's probably unusual but I've never met my co-author. We began corresponding via email and then one day decided to write a book. We'd each write a chapter and email back and forth. Because she's incredibly easy to work with it was a great experience. So that's my advice when it comes to partnering up in any endeavor, never meet your partner. If you actually meet the other person then you start noticing little things that make it harder to work together. Like maybe you don't like the way they dress, or talk, or comb their hair. It's better to never even say hello. I think that's especially true in comedy where a lot of writers have the people skills of turnips.

This has worked out well enough that I don't plan to ever meet any future work partners. Although if it's a very long work relationship, lasting years, I may consider speaking to them on the phone. But only after testing the waters by instant messaging.