Lonely this Valentine's day? Ben Karlin feels your pain. As the editor of Things I've Learned From Women Who've Dumped Me, the former Emmy-winning executive producer of The Daily Show With Jon Stewart and co-creator of its sister program The Colbert Report turns his focus from the political to the personal, collecting hilarious-yet-touching essays on ill-fated relationships from various well-known writers, comedians, musicians, and a former U.S. Senator. CollegeHumor recently spoke with Karlin about the book, Valentine's Day, and the comedic merits of getting kicked in the nuts.

What's your opinion of Valentine's Day? Sweet-natured holiday or Hallmark scheme?
All I know is St. Valentine died for our sins and we honor him by eating chocolate shaped like a bunny. If that doesn't make you weep, I don't know what will. I should mention I was home-schooled.

Do you consider yourself romantic?
I consider myself romantic in the worst possible way. Like, hopeless and pathetic and pie-in-the-sky, not "romantic carriage ride through Central Park while 'That's Amore' is playing somehow in the background." My romanticism is rooted in the impossible and unknowable and I am basically damned to life of eternal disappointment because of it. Piece of advice: Saying the above does NOT work as a pick-up line.

Many of the contributors to Women Who've Dumped Me are comedians. Is there a specific correltation between heartbreak and comedy?
Turning something bad into something useful is probably deeply coded in all of us, but comedians and artists are particularly adept at taking things like rejection, or being an outsider and using it to fuel an interesting point of view on life. Also, all comedians and writers are heinously ugly — ergo eminently dumpable.

Was it a big adjustment switching from the political humor of The Daily Show and Colbert Report to a topic as personal as breakups?

I don't really see it as different, in the sense that the process for me is the same. Figuring out a take on something that is in line with my sensibilities. Obviously, subject matter and format shifts, but I sadly only know how to do things one way. Because the audience is largely unknowable — the fact that some of this stuff is personal doesn't really register with me. If I was famous, and people were coming up to me and were like, "Dude, stop sharing," it might affect me more.

What's funnier: politics or relationships?

#1 Source of Humor: Getting kicked in the nuts; #2 Source of Humor: Human relationships; #3 Source of Humor: Britney Spear's vag/public dismantling; #4 Source of Humor: Politics.

That's not my list. There have been studies done to back that up.

Some of the sections, including Steve Colbert's and Bob Odenkirk's, are written in a format more unusual than a straightforward essay. What guidelines did you give the writers regarding their pieces?

The only rule was to not talk about Fight Club — which really confused some people for a while. Eventually I relented, and just asked people to make sure their piece was somehow grounded in reality and formatted in some way like a lesson. Beyond that, I let them decide everything else.

Did any of the writers surprise you with the emotional content of their essays?

Dan Savage, who is hilarious and normally extremely blunt, really surprised with his extra blunt-ness. When I first read his piece, I think my eyes bugged out a bit – which is highly unusual and Zero Mostel-y of me. There isn't a lot of sentiment in the book, but I thought Damian Kulash was as honest as one can be about the death of a relationship, while still being really funny.

What advice could you give to younger readers experiencing their first brushes with heartbreak?
Depends on how young we are talking. From what I understand by looking at the internet, today's teenagers are plowing through relationships and doing it at a pace that virtually guarantees the entire world will have had sex with each other by 2019. Then again, the internet may not be reliable. The best thing I learned from doing this book is that life is actually quite long and human beings are pretty fucking resilient. They bounce back from almost anything — even when it seems like what happened is un-bouncebackable. None of the essays in the book are bitter or hateful, even though they could have been. That's kind of hopeful.

Also, don't be creepy.