A question I’m often asked is why do you always wear a hat? When people see me without a hat they are surprised I have hair. Usually, they just assume I’m bald. I’m not… yet.

My answer to this question isn’t what you were expecting to read right now, it’s actually kinda deep.

The quick and surface answer to why I always wear a hat is because I like hats. I always joke And say I wasn’t hugged enough as a kid, and wearing a hat is like getting a head hug. But there’s a much more complex reason as to why you rarely see me in public or take pictures without a hat.

Many of you already know I was born with poverty genetics, genetically challenged. I have the thinnest, stringiest hair on the planet. There are seven-year-olds out there with thicker hair under their armpits then I have on my head. No matter what haircut I get or what style I try to do, my hair always looks like crap. So there’s that reason, but that’s not the real reason why I always wear a hat in public and in pictures.

In my last relationship, my ex-wife brought a scary truth to my attention. She told me because I’m so transparent on the air and share my entire life with the listeners that she feels like there’s not much I keep just for her. She said she feels less special because I share myself with the world and her so there is no longer that one on one private connection. This hit me hard because she was so right. Nothing was safe, if we had an argument I would talk about it on the air, the listeners had seen me naked, they knew my deepest secrets…I really didn’t leave much for just her. I was so focused on being 100% honest and transparent with the listeners that I lost touch with my ex’s needs and privacy.

After a “come to Jesus” moment, I finally understood my ex’s feelings and her needs. In one of her requests to keep exclusivity and to regain some privacy, she asked me to never get naked again on video or for pictures. She wanted to be the only one to see my naked body, which I totally understood. If the roles where reversed, I’d lose my mind if she got naked in front of her coworkers.

Another thing she requested was that I keep one thing about myself secret for her. Something about my body or life that only she knows. She was worried I was whoring myself out for a cheap laugh and losing my privacy in the meantime. Again, she was correct. I joked with her and said, “nobody knows what my feet look like”. She didn’t bite on that and didn’t laugh at my cheap joke.

That’s when she said, “you always wear a hat on the show. Nobody knows what your hair looks like. Why don’t you always wear a hat for pictures and videos?”

At that point, I knew I screwed up big and was almost willing to agree to anything. But when she threw that easy answer to a big problem, I took it. So from that day on, I have worn a hat in every picture or video, and I’ve worn a hat at every appearance and event.

And now that I’m divorced, it’s just habit. I feel naked without a hat on. I have taken new photos without a hat on though, The freedom feels amazing. It’s like posing for the centerfold in Playboy.

So long story even longer, that’s why I always wear a hat. It started as a silly compromise to a big relationship problem and it turned into a habit.

(Side note about hats. I’m a huge fan of minor-league baseball hats, Have you seen the Chicago Dogs hats?! They are awesome! I’ve got to get my hands on a hat!)