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Wednesday, January 28, 2015 |  Madison, WI: 25.0° F  Overcast
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Tell All: A naked biking first date
A good idea or not?

Dear Tell All: I'm a 25-year-old man who prides himself on having a good body. As secure as I am about the way I look, however, I'm really insecure around women. When I'm interested in someone, I always seem to say the wrong thing - if I can think of anything to say at all. As a result, I've had surprisingly little experience with sex or romance.

I currently have a crush on a woman at work. She's gorgeous and intelligent, as well as being a couple steps higher than me in the company hierarchy. I have a sense that she could be THE ONE - a real soul mate. But I'm afraid to say much to her for fear of blowing it, given my awkward way with words.

This brings me to the World Naked Bike Ride. I've been following plans for Madison's version of the event on June 19. I have this crazy idea about asking my coworker to go on the ride with me. She has a sense of humor and a bit of a wild streak, and I think she might say yes on a lark. I wouldn't present it as a "date," but I'm hoping that sparks would fly during our naked jaunt through Madison. I could show off my good qualities - the ones she can't really see in the office, when I'm fully clothed.

Hopefully she'll be impressed, the ice will be broken, and I'll have an easier time talking to her in the future. Do you think it's a good idea?

Strong Silent Type

Dear Strong: You cut me to the quick. Do I think it's a good idea for you to bike naked through the streets of Madison with your hot coworker? OF COURSE I THINK IT'S A GOOD IDEA! What am I, one of those tut-tutting advice columnists the Wisconsin State Journal runs? Let me know how it goes.

Or better yet, I'll head down to the World Naked Bike Ride route and see for myself. This sounds like a first date everyone will enjoy watching.

Do you have a question about life or love in Madison? Write Tell All, 101 King St., Madison, WI, 53703. Or email

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