Chester the Old Man's Teen Advice

By Asher Hancock:



Hello, if you are a newcomer to this column, the name is Chester, Chester Boone. My friends call me “Chester” and my readers call me “old.” You’ll come to realize that we like to joke around here. I’m 85 years young. I know what you’re thinking and yes, Benjamin Franklin was my roommate in college. I warned you about the jokes. Every once in a while when my scurvy is under control, I like to take some questions from teens and give my advice. My great grandson Charlie recently taught me about these things called “Stans” and apparently I have them. My less great grandson Sven dubbed my supporters “The Boone Brigade.” I sent out my squire to announce that I would be accepting questions and the Boone Brigade delivered. Actually, I just posted on MySpace, which is the place to be according to the latest addition of 2006 Magazine. Without further ado, I present some advice for teens from the internet’s resident old loon, Chester Boone.


Hey Chester. My name’s Chris. I’m 16 years old and I’m just starting my junior year in high school. Virtual classes are pretty new to me and I made a big mistake. In one of my classes, I didn’t realize my microphone was on and everybody heard me arguing with a stuffed animal about whether or not I should ask out my crush. She was in the class and now everybody thinks I’m weird. What should I do Chester?

Hey Chris. Now, I did some thinking while I was feeding the birds at the park. It seems to me that if you are the type of kid that argues with stuffed animals then I’m sure everybody already thought you were weird. However, I think I have a solution. I had a very similar experience when I was a 15 year old kid. My friend Clem and I were at a local speakeasy smoking cigarettes and drinking Shirley Temples. My favorite new song at the time, the Pledge of Allegiance, played on the jukebox. I was debating with Clem whether I should get up and dance. Keep in mind that dancing was illegal in my hometown, like Footloose, and I was at risk of serving 10 years if I did it. Clem kept telling me not to do it, but I knew in my heart that I had no choice. I stood up on that table stripped all the way down and started doing the twist. Before I knew it, I was being driven away in a police cruiser, which was a horse and buggy back then. After I got out on bail, I fled to Guatemala, where I lived for 3 years until the laws changed. So what you need to do, Chris, is commit to your heart and publicly ask out your crush the next time you have class to try and seal the deal. I married my first wife when I was 16, so it’s important to lock down a nice girl while age is on your side. If she rejects you, flee to Guatemala for a couple years and wait for everything to blow over.


Dear Mr. Boone. My mother keeps imploring me to make my bed and clean up my room. When I do not she takes away my Xbox. It seems to me that life’s too short to waste time on cleaning up and that the cleanliness of my room has no major impact on society. I’d love to know your thoughts on the situation and how to get my mom to stop bothering me. Sincerely, Thomas.

No need to be so formal young lad, or as the kids on my street like to say, “homie.” I do live in a home and I guess that is cool nowaways. I’ve heard of these Xbox things and let me just tell you that when I was a little kid, I had a cardboard box that I pretended was a spaceship. And spaceships weren’t even invented back then, so you can see my imagination really was amazing. When I was 7 and started smoking cigarettes, like kids did back then, I accidentally set the box on fire and my mom refused to get me a new one. After that, my primary form of entertainment became kicking a tin can down the sidewalk which got pretty wild. I understand your predicament, I truly do. Word on the street is that moms nowadays can be pretty lame sometimes. When I was younger and got in trouble, my mom used to punish me by sending me to work 12 hour shifts at the steel mill, but your thing sounds bad too. My advice would be to stick it to your mom by letting her take your Xbox away and going out and building strong relationships more meaningful than any game. Work to get straight As, go to a prominent college, and enter into a highly fulfilling career. Try to solve at least three of the world’s major issues. Never make your bed or clean your room once. That’ll show her! If that seems a little too difficult, Tommy, then just do what she says or you might have to start paying rent.


Booney Tunes. What up? It’s me, Ragnar, you’re favorite nordic teenager. I’m here in Sweden, just kickin it. I got a quick Q for you CB. I’ve been partying, like really hard, like us Swedes do. The squad has been buying a lot of soda and staying up past midnight, even on some school nights. Recently one of my friends dared me to try some non-alcoholic beer. I’m not trying to be a dweeb, ya feel, but I’ve heard it’s a gateway to some pretty nasty stuff like real beer. I’m worried the bros might ostracize me if I can’t hang. What is a Scandinavian to do without his boys? What’s the move Boone?

Ragnar, it seems that you send me a new question every week and I am still yet to understand half of what you say. You also have to stop writing suggestive fan fiction about me, it’s pretty weird. Also, according to your fan mail you turned 25 last week so happy birthday I guess. I thought it might mean that your brain has finally developed enough for you to realize the definition of “teen advice column,” but here we are once again. Back in the 60’s I did horse tranquilizers and showed up at random protests. I once ended up doing Shrooms with Paul McCartney. Here you are telling me you're scared of a non-alcoholic drink that is a gateway to nothing but further sobriety man. You’re in your twenties, have a little fun. Maybe it’s time to drink a real beer, especially considering you’ve been of age for 7 years. If you are so worried about being abandoned by these so-called “bros” maybe you should find some new ones all together or just flee to Guatemala and start a small coup to take over the country. Unfortunately that didn’t work for me as I then had to flee to Saudi Arabia, and began working in the oil fields. Speaking of which, I think it might be time for you to get a job. And no, your OnlyFans account on which you showcase your stamp collection does not count. It’s clear that your mom is the only person who is going to pay to see that. Try and get a job at Target or in Colombia laundering money for a cartel for a few years. Wow I’ve had some good times. Maybe if you take any of my advice for once you’ll stop writing to this column, and I can finally take that vacation to Colombia to pick up some laundry I left there in the 70’s.


Tune in Next Time for more advice for the internet’s resident old loon, Chester Boone!


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©2018 by The Milking Cat.