Flippin' Our Shades at Author and Comedian Dan Wilbur

photo courtesy of Anya Garrett

Dan Wilbur is awesome. Aside from writing for Collegehumor.com, McSweeney’s, and the Onion News Network, Dan also created the site, Better Book Titles. He recently wrote the humor book “How Not to Read: Harnessing the Power of a Literature-Free Life” too. A mutual friend put us in touch a few weeks ago because she thought we'd get along. Guess what? We did! In fact, we struck up a bit of an Internet pen-pal correspondence. It was great. So, when I saw that he'd be here in Philly tomorrow, Wed. Oct. 17th, doing a reading at Literary Death Match at the World Cafe Live, I figured it'd be the perfect time to ask him some questions about dating. 

SK: What's your idea of a perfect date? 
Dan: We go out with seven to twelve other people to see Titanic for the fourth time. You whisper which parts are your favorite parts as they happen, then we break up in the middle of the film and I go home alone, feeling great because it means I can play Final Fantasy VII and no longer have to watch Titanic. I have not been on a date since 5th grade.

SK: What do most guys do wrong when they're out with a girl?
Dan: Number one with a bullet: telling the person you're on a date with that you already have a girlfriend. That makes girls SO mad! Don't do that. Another common mistake is mentioning that you're a comedian. I would save that for year three of marriage.

SK: What's the worst thing a girl can do on a date?
Dan: I'm a big fan of over-sharing. I realize this might be terrible dating advice, but I love it. It's like gossiping about yourself, let's me know you're comfortable with emotional things, and it shows a little trust. So when I meet someone who actively wants something hidden but mentions it in passing because in reality she wants to reveal it, the only thing you can do is pry (me) or ignore it (awkwarder me) and there is nothing fun about either. Don't say, "Oh, then my last boyfriend..." and trail off because you think it's a mistake to talk about that. OUT WITH IT! I've had girlfriends! I want to talk about it.

SK: Tell us a secret!
Dan: Ever since my mom stopped picking out pants for me, I enjoy shopping for clothes. Also, in video games where there's a choice between good and evil (like Fallout 3), I always choose good even though I'm supposed to do whatever crazy thing I want. This might sound like I'm trying to say I'm a good person, but I'm not. It's compulsive.

SK: What advice would you give a younger version of yourself about dating?
Dan: Trust your hunches. If it feels like a person is slipping away, be the first to acknowledge it rather than asking what's on your partner's mind. There's nothing worse than asking, "What's wrong?" when you know exactly what's wrong, and hearing "Nothing [sigh]." Smoke less pot so you can be less awkward about the whole talking thing. Also, CALM DOWN. Not everything means you're married. That's what getting married is for.

SK: What would you put on a mix tape for a girl that you liked? 
Dan: Too much Dylan, not enough hip hop (that tells you something!) Also, Chris Isaak's "Wicked Game."

All this and brains too! He's @betterbooktitles on Twitter and you should follow him immediately.