This isn’t a story about somebody holding up a gas station food mart.

No, that would be much more comfortable.

Late Wednesday morning, I walked to the gas station near my apartment and went into the market portion and waited in line behind a man who looked to be in his late 40’s or early 50’s. He was buying a copy of the Chicago Sun-Times and a pack of smokes. He was wearing a camo hat with a burly jacket and rugged jeans. He had finished paying before turning toward me and my eyes scanned down to notice he was wearing high heels.

Picture Larry the Cable Guy wearing high-end pumps from Neiman Marcus.

Now, my first instinct was to say something along the lines of, “You lose a bet?” This is the middle of football season and the World Series just ended, so the odds were in my favor. However, I froze and didn’t say anything because of the fear. What, if on the off-chance, that this is something that he enjoys doing. He enjoys going out duck hunting and fishing and just happens to enjoy wearing high heels – “I’m Larry David. I happen to enjoy wearing women’s panties.”

I worried that if I said, “You lose a bet?” it could offend him because why would the only reason this outdoorsman is wearing high heels is because he lost a bet? I got lost in the middle of the sea of political correctness on one side and the disingenuousness of seeing a man like that wearing high heels and simply saying, “Boy, this rain we’ve been having sure has been a damper,” on the other. It was such an elephant in the room that I seemed to get lost in it’s size.

There’s debate on whether that political correctness is good (it saved a man who happen to enjoy women’s high heels from embarrassment) or bad (it prevented a potentially hilarious interaction about the reason this guy was forced by somebody to wear these women’s shoes).

Having lived two-thirds of my life in Portland, I’ve seen men wearing high heels. I’ve seen middle-aged men wearing a free-flowing dress that only guys who wear dresses wear and it does nothing for me. Good on you, brother, I love how you do it mostly for shock value. This one felt different, though. Usually, those guys aren’t walking back to a big red truck and don’t look like they have a Skoal ring in their back pocket.

I actually found that I was upset I didn’t say something. It was so noticeable that if he was somebody who got his kicks wearing women’s kicks, he probably got it all the time and I would just be one more person piling on. However, the emotional connection we could have had talking about the game that he bet on and he could have had somebody to share and laugh over the absurdity of it all could have helped him.

You win this round, outrage cycle.