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Fake News

8 Times I Regret Wearing Jean Shorts Instead of Dress Pants

1. My First Date (April 25th, 1997)

I remember this one very well. It was the first time that I decided to ignore the wishes of my mother, father, sister, grandma, grandpa, aunt, uncle, cousins, and friends by going ahead and wearing my jean shorts wherever I wanted to. This was for my school’s junior prom. I asked Sally Hander to go with me and boy, was nervous. I wore my jean shorts to try to help relax, as they have always done for me in the past, but everyone kept staring at us when we were at the dance. (Dancing in jean shorts is really comfortable, by the way.)

Sally finally hit me on the head with her purse and walked out because I kept telling her that everyone was snickering and pointing at us because of how bad she was dancing and how bad her makeup looked and not because of my jean shorts.

2. My Wedding (August 25th, 2006)

This was just ridiculous on my part. Honestly, I don’t know why I thought this would fly. My wife (now ex-wife) even specifically mentioned to me the day before to not “even think about wearing” my favorite jean shorts. I think I just wasn’t ready to settle down with some nice dress pants yet. Or that woman.

3. My Brother’s Wedding (July 19th, 2008)

I thought this would be a good joke considering what had happened at my own wedding a few years before. It’s not MY FAULT my brother asked me to be his best man and I ruined the stupid photos. He could have just had us all wearing jean shorts.

4. My First Professional Job Interview (May 6th, 2003)

Before you jump down my throat telling me how obvious this one was, the interview was at a company that SOLD JEAN SHORTS. Sure, the guy interviewing me had a suit on, and so did everyone else in the office, but I thought it would be good to show my support for their product.

Fine, you know what? Whatever. You sound just like my ex-wife.

5. My Visit to the “International No Pants Swingers Party” in Atlanta (June 2nd, 2004)

I was definitely misinformed as to what this event was celebrating. It did feel odd being overdressed in my jean shorts, though.

6. My Press Conference Announcing of My Formal Bid for Mayor (May 29th, 2007)

As the Tri-County Free Press reported of the incident, “We just rid ourselves of one mayor who treated our city finances like a joke, do we now need a man who treats his wardrobe and our sense of public decency as such?”

7. My Father’s Funeral (December 14th, 2014)

This was a really sad day for me. I told everyone that I would be most comfortable in my jean shorts. When I gave the eulogy, it didn’t help that my Aunt Carol kept tugging on my mother’s sleeve asking why I was wearing jean shorts. It was really rude and distracted me and I got off-track, which is why I started talking about how the moon landing was staged.

8. My Mother’s Funeral (February 12th, 2015)

Mother didn’t last long after father passed. Everyone was shocked at how quickly she went, but apparently not as shocked as they were to see me in jean shorts again.

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