What's something dumb you did as a kid/teen that felt petty at the time but feels terrible in hindsight?
Here's my story for that.
When I was in middle school back in 2011-2012, there was an old still-running Pepsi vending machine in my (very small) town that was owned by a local business. It sold pretty much all of the major soda varieties at 50 cents per can. They were ice cold, too. I happily used it like I was supposed to for quite some time, often stopping by it while walking home from school. But of course being a broke young teen who wasn't old enough for a job and whose parents weren't terribly well off themselves, I didn't always have change on me for the machine, so getting my 50 cent soda was still more a privilege than a daily thing.
Well, eventually, one of my more streetwise friends found that the machine could be easily opened up, and you could reach through the outside cage and take the sodas for free. And well, us being the roaming group of bored poor kids we were, once he told us, we all got in on nabbing sodas from that machine. Most of the time 1 or 2 of us would just swoop by and nab 1 or 2 sodas, but there were a handful of times where we came over as a group and made a whole organized heist out of it, with 1 or 2 kids working the machine and filling a backpack with sodas, and the rest of us posted up all over the area keeping watch in all directions, even using hand signals to warn each other if a car or person was coming nearby. There were no cameras nearby that we knew of, and we generally did this at night, but there were a couple more bold operations carried out in broad daylight.
This happened off and on for... I wanna say around 6 months before we realized hey, maybe some of us don't want to get in trouble. The business owner almost certainly knew what was up as well, as he installed a motion light over the machine and eventually fixed the lock that we kept prying open. But, he never confronted us, we were never caught, so, after growing out of it we sorta just forgot about it.
Until a few years later in High School, when the business owner came to the school to be one of those motivational guest speakers. Me and much of the old squad happened to be sitting together attending his speech, and towards the end of it while talking about how your actions can affect others and whatnot, he brought up how some years ago some kids were stealing sodas from his vending machine, forcing him to fix and secure it better which was very difficult for him. He was a disabled Veteran (ofc we didn't know this at the time of the soda stealing), and he kept repeatedly looking right at me and my buddies during that specific part of his speech.
We all agreed that the old man more than likely knew it was us, but for one reason or another, chose not to confront us, call the police, or say anything about it until that day years later. If his goal was simply to make us regret our past stupidity, well, it worked. We all felt terrible for the rest of the day.
TL;DR: Stupid Middle School Me and his equally stupid Middle Schooler friends stole cans of soda from an old vending machine repeatedly, came to deeply regret it years later when we found out the owner was an old disabled veteran who struggled to restock and repair it- something he seemed to directly tell us during a school speech.