One Man's Quest to Be an Esquire Man

In their Summer 2010 issue, Esquire devised guidelines for how men are supposed to age. They published a list that details the transitions men make and the transitions they should make between the ages 18 and 59 years old. Since I recently turned 23 I decided to check how poorly I match up with the Esquire ideal, and how I see myself aging in the future.

Age 18
The Esquire Man: I’m supposed to be making the transition from reading Narnia and Lord of the Rings to On the Road, Naked Lunch, and Fear and Loathing in Las Vegas.

In Reality: I was reading the 6th Harry Potter book, while secretly dreaming of still being able to attend Hogwarts School of Witchcraft and Wizardry. I read the first five pages of William S. Burroughs’ Naked Lunch last month in Barnes and Noble, preceded to go home and re-read Catcher in the Rye instead. Still never read Kerouac. Watched Fear and Loathing in Las Vegas while drunk at 4 am in college.

Age 20 (Apparently 19-year-olds don’t matter to Esquire)
The Esquire Man: At this point I should start thinking twice about posting Facebook photos that involve drinking and smoking along with the blackout pictures that are sure to follow. The 20-year-old Esquire man is always wary of what future employers can find on the Internet.

In Reality: My grandparents recently made a point of telling me that they don’t think a photo of me exists without an alcoholic beverage in my hand. As a journalism major I just considered it training for the real world.

Age 21
The Esquire Man: It’s time to suit up! When a man is legally able to drink, what he should really be thinking about is investing in navy, wool, two-button, and single-breasted suit.

In Reality: My father’s old Polo suits fit me perfectly and I look good in them. Esquire can’t convince me otherwise.

Age 22
The Esquire Man: Now I’m supposed to be making the transition from On the Road, Naked Lunch, and Fear and Loathing to For Whom the Bell Tolls, The Naked and the Dead, and Deliverance.

In Reality: I read For Whom the Bell Tolls! Meaning: over the course of the first four years of becoming a man I’ve reached 1/16 of Esquire’s guidelines. Points.

Age 23
The Esquire Man: Make the transition from listening to bands no one has heard of to becoming familiar with the entire catalogue of Bob Dylan and Leonard Cohen.

In Reality: Still trying to listen to bands no one ever heard of, because it’s kind of my job. And I’m comfortably familiar with Dylan’s catalogue, however I will always like Springsteen more.

*At this point, I make the leap from life experience to complete speculation, boarding on bullshit, about where I could be during milestone birthdays in my life.

Age 25 – The Quarter Century Mark
The Esquire Man: Apparently the Esquire Man has watched Paul Blart: Mall Cop and is finally making the transition to Jason Reitman films such as Up in the Air.

In Reality: The fuckin’ Esquire Man has watched Paul Blart: Mall Cop! Ugh, I might have to puke up my Cinnabon. I’ve watched and enjoyed Thank You for Smoking, Juno, and Up in the Air. Guess who’s ahead of the Esquire Man aging curve? This guy.

Age 30
The Esquire Man: No longer boot and rally. Now puking means the end of the night and shame.

In Reality: This would be a sad day. I could see it happening, but I don’t want to admit it. I’d like to say I’d be too much of a man to vomit from excessive drinking at that point in my life. I’d hope to have it down to a science, like my prowess at Jenga.

Age 35
The Esquire Man: Knows the different types of wine glasses that go with different types of wine.

In Reality: I mean I enjoy drinking it and I know white wine goes with fish and red with meat, but differences in wine glasses? Wow, tough one. All I know is my dad doesn’t like the big glasses because he doesn’t think he’s drinking too much, when he totally is.

Age 40
The Esquire Man: Is losing interest in fantasy football, because he’s taking an interest in his health. The Esquire Man knows his blood pressure, cholesterol levels, and sperm count. (Just kidding the Esquire Man stops making jokes like that at least eight years ago)

In Reality: Real fans don’t care about fantasy sports anyway because it takes away from the game. You start rooting for your sworn enemies to sack your quarterback or to hit a home run. And with the amount of steak and other manly foods I devour, I’m definitely going to stay up to date with my health stats. That is if I have health insurance by then.

Age 50 – Half-Century Mark

The Esquire Man: Stops making a big deal out of prostrate exams and becomes accustomed to probing up his ass.

In Reality: No fuckin’ way. Nope. Not getting used to that. Nuh uh. No can do.