Tough Questions: What’s the Most Trouble You Ever Got in Before You Were 18?


Every week we ask everyone who hangs out around here to answer a tough question. This week:

What’s the most trouble you ever got in before you were 18?

Rules are simple: when did a grownup threaten to send you to jail for something you did before you could drive? Read on to hear some stories about stupid kids being stupid kids at their damn stupidest. Sidenote: these are some of my favorite responses all year. Ain’t no one over ANY of this.

Alex Russell

In 8th grade the principal at my middle school gave a speech one morning about how students shouldn’t hand out in the hallways, but should go straight to homeroom when they got to school. I had a visceral reaction to this and I flipped off the intercom. It wasn’t anything I thought about, I just did it. My teacher at the time was one of my favorites I ever had, but she had to take me to the office, I get that. I had no perspective at all on this middle school principal or if he was happy with his job or how he’d respond to a young teenager flipping him off indirectly. Turns out it was worse than I could imagine. I didn’t get in trouble a lot in school and I never really adjusted to it with the “COME AND TAKE ME, Y’ALL” attitude I always hoped I’d exude in the moment. I freaked out, even when it got ridiculous and he turned red and threatened to send me to jail. That actually happened. He said “maybe we should send you to a correctional facility?” I got suspended for three days, but if they want me in jail for that one NOW YOU GOTTA COME TAKE ME.

Brent Hopkins

I was pretty lame as a kid so the most trouble I got into was for cyber-bullying before that was a major thing. I kinda snapped on one of my classmates/friends on a message board and this led to a super awkward guidance counselor conversation and a mild threat of police action if it continued (knowing what I know now, this was not actually possible). I obviously backed off and haven’t had an issue like that since, but apparently I was the hipster of cyber-bullying doing it before it was mastered by 4chan and the likes.

Andrew Findlay

In 10th grade English, we were given an in-class assignment to write a sonnet. The sonnet is such a limiting and exact form that no 10th grader will ever, ever write a good one. I was offended that my teacher would so clearly set me up for failure, and wrote “This is bullshit” on my paper, just for me. She swooped down the aisle, picked up my paper, and next thing I know I was in goddam in-school-suspension. Which, I gotta say, is bullshit. You sit in a cube, talk to no one for eight hours, and do schoolwork nonstop. Even if it doesn’t quite knock it down, it seriously treads on the toes of the 8th amendment. I did a bunch of stupid shit as a teenager, but as far as consequences, that was the worst. It’s weird – my dad was super strict, but whenever I did something involving wheels-falling-off stupidity, he reacted really differently. For example, I once got grounded for a month for talking back, but I received no punishment whatsoever the time the police woke him up with a phone call to tell him about the stupid shit they’d caught me doing (it involved fireworks).

Jonathan May

Man oh man, when my parents found out I was smoking cigarettes, I was in a shit-ton of trouble. I was 16 and working at a party supplies store that basically functioned as a pre-alcoholic training facility. There was always a cooler filled with whiskey and tea in the back, and believe me, people would help themselves. People were also free to smoke cigarettes (among other things) in the back of the store as well. One day, my brother and sister stopped by to visit and found me smoking in the back. I swore at them up and down when they promised to tell my parents, which they eventually did. My parents were fuming! I had to quit that job and take one closer to home, because they also took away my truck for a few months. I forgave my brother and sister for being uptight prudes, and thankfully they’ve come around to being normal human beings. But I still haven’t quit smoking. Yet.

Tough Questions: What’s the Dumbest Thing You’ve Done to Yourself Lately?


Every Monday we ask everyone who hangs out around here to answer a tough question. This week:

What’s the Dumbest Thing You’ve Done to Yourself Lately?

Rules are simple: everyone does stupid things and everyone does things that aren’t in their own best interest, but when have you last combined the two mistakes to form a delicious fusion mistake? You do it to yourself, you do, and that’s what really hurts.

Alex Russell

I went to Dallas last weekend on a last-minute trip. I booked the tickets just a few days before leaving because I originally wasn’t sure if I was going to be able to go or not. In my haste to do so I apparently booked a trip that left Chicago on February 20th and returned from Dallas on March 24th. I discovered this when the helpful woman at the Spirit Airlines desk alerted me to what month it is. Turns out that I don’t know what month it is, and Delta Airlines was happy to take $200 from me to fix my stupid mistake. I briefly considered lying when retelling this to make myself look better, but no, I sincerely just booked the stupidest plane ticket of all time. No need to sugarcoat it. I can’t believe I can dress myself (most days, kinda, debatable).

Scott Phillips

I’ve done some stupid stuff in my life. Most of it as a result of drinking. But since I’ve slowed that down and started to become an adult, my dumbest thing I did was probably go through this ridiculous Chicago winter without a hat and gloves. I got a new winter coat courtesy of my girlfriend and I never decided it would be necessary to cover my hands and head for the rest of winter. Which was really smart, because it’s February 26th and we STILL had subzero temperatures when I left the house this morning. Definitely not the brightest move in my book, but now it’s nearly March and I’m too stubborn to get them at this point.

Austin Duck

Recently, shit got real, and I started smoking again. Worst. Mistake. Ever.

Alex Marino

Thrillist put out a list of the best pizza places in Chicago by neighborhood and I was dumb enough to read all the idiot fucking Yelp reviews about them. Yelp reviews are the smallest step above right-wing blog comments sections except I rely on Yelp for restaurant ideas while comments sections are mostly avoidable. I read this one particular review that gave a place two stars because it wasn’t as good as the pizza they grew up with in NYC and what they had when they traveled to Italy. The person that wrote it should have their Yelp posting privileges revoked by court order, their computer thrown off the top of the Leaning Tower of Pisa, and the pieces of the computer baked into a thin crust pizza they can shove up their ass.

Brent Hopkins

I think if there was a way to win the tough question I actually may win this one. The dumbest thing I did to myself happened right before I came home from Korea and I was going to my new job to maybe meet my new employers. I was cleanly shaven and honestly fresh to death, as they say, but I had one problem… My nose. Specifically, my nose hairs had grown to unruly lengths as my trimmer had broken and I hadn’t picked up another one. I was alone in my apartment and — I have no idea why I thought this was a good idea — I decided that the best way to to handle the problem was to channel my inner military tactician and “burn the fields,” so to speak. I grabbed a lighter and proceeded to burn the nose hairs in one nostril and then, as the smell of seared hair filled my nasal passage, I dropped the lighter and said “What the hell is wrong with you? Are you an idiot?” Luckily, I managed to hit only the nostril and didn’t sear off my eyebrows, but I had the smell of cooked nose hairs for a few hours to remind me that spending that much time alone can be dangerous to your health.

Jonathan May

Of the myriad dumb things I’ve done to myself recently, I’d have to say pissing off the checkout lady at my regular Walgreens takes the cake. I simply asked if they had more iced tea, but after ten minutes of searching, she said she could look in the back. As I was on my way to school, I blurted out, “No thanks, I’m in a hurry.” I realized as I said it that I had officially pissed her off. A blizzard passed between us in those ten seconds following. Fuck, I thought. So now I have to go to Walgreens the night before, when all the weirdos are out.

Andrew Findlay

I recently went to a movie downtown. Finding parking in DC is usually mildly time-consuming, not terrible. I found a likely spot, left my car, and walked away as I pulled up the parking meter phone app. When I clicked “pay,” the program said “parking not available in this location at this time.” I have no idea why this information simply made me shrug my shoulders and keep walking to the movies, but it did. Come time to go home, my car is gone. My wife calls the number on the parking meter, and the dispatch lady tells us it was deposited at 10th and G, a block away from where we are standing. We walk down a ways, find it, and there’s a 100 dollar ticket for parking in a rush hour lane, a 100 dollar charge for the tow, and a pink sheet itemizing the damage the tow truck did to my car. You know the amazing scene in Forrest Gump where he tells Jenny that he’s not a smart man, but he knows what love is? The first part of that, only the first part, was playing on repeat in my head for a while after that night.

Mike Hannemann

The dumbest thing I’ve done to myself lately was to take what I like to refer to as an “unfamiliar bus.” The bus is terrifying to me, but I figured what the hell, I can do this. I decided that I would take a bus route home from work, rather than the train, so I could stop off at a Best Buy to get a new video game. I had the entire thing planned out hours beforehand (I Googled several routes) and knew what I was going to do. Then I ended up on the wrong bus. So I got off after one stop and got on another one. It was also the wrong bus. Five minutes later I realized this and got on another bus. Spoiler alert: It was not the right bus. After a total of five buses I got where I was going. The best part of the story is that, at 30, I got this lost trying to buy a Donkey Kong game. At the very least, I earned the adult equivalent of a participation ribbon.