10 Craziest Things People With "Chill" Parents Were Allowed to Do

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Having chill parents can come with some unexpected benefits, particularly when it comes to the freedom they allow their children. While many parents impose strict rules and limitations, some take a more relaxed approach to parenting, allowing their kids to explore and experiment with a wider range of experiences. This can lead to some truly wild stories, as children with chill parents are often able to get away with things that their peers could only dream of.

1. Young Adventuring

“I was allowed to saddle up my horse, take my Savage 22/20 gauge over/under gun, some beef jerky, a canteen, a sleeping bag and bed roll tied to my saddle and ride up into the Ochoco Mountains and camp over night. Then ride back the next day. Also did the same with my motorcycle. I was about 13 or 14 at the time,” one guy shared.

2. Lighting Fake Trees on Fire

“My friends mother was an extremely relaxed parent, he could do pretty much anything and she would say Patrick, Stop. Well one fine December day my friend thought it would be funny to see how flammable the fake trees are, he lit a match and held it to the plant, we were still in his house at this point when the plant caught fire. He picked it up and tried to put in to the sink to spray water on it, but the faucet didn’t reach the plant. My brother picked up the plant, now this thing is fully on fire, and threw it into the snow. His mother stood there the entire time, watched this whole thing go down and only said to Patrick, don’t do that again,” one person recalled.

3. Supporting the ‘Rebel’ Phase

“My mother told me at an early age that one day I would rebel, and instead of fighting me she’s going to guide me through it. Said that she’d rather know what drugs I’m doing and which women I’m dating so that she can provide said guidance than for me to hide it. Said that she wanted me to “sow my wild oats” while I was young, so that I could buckle down when it really mattered. And, well, that’s exactly what she did.

And all of it was absurd.

We were dirt poor, living in a mobile home in the bad part of town when I turned 12. Between child support, disability and welfare she was only getting about $600/mo. (when she went after my father for more child support, raising it from $50/mo to $400/mo he counter sued for custody… that was fun…) So, she had to sell drugs to get by. Making our trailer the trailer everyone always hung out at. My teenage years were a non-stop party. I’d normally wake up to find upwards of 10 people crashed on the floor. In a single-wide.

I started smoking, drinking and being sexually active at 12. Weed at 13, acid and meth at 14. I was also 13 when I had my a girlfriend move in for the first time. She kept running away from home, the last time getting in a truck with a random dude who was going to take her to texas… and our mom’s agreed maybe it was best she stayed with us for a while. From that point forward my mother had no qualms with girls sleeping over. That said, I haven’t had an empty bed since I was 15, and have zero experience being single. (which I see as a bad thing, but what can I do …)

While my home life was a constant party, school life was miserable. I was always the hated kid. The poor, dirty, dorky kid, that people loved to mess with for the sport of it. The rest didn’t want to associate with me out of fear of being targeted. …Because of the contrast between home and school I had a tendency to, well, not go. Got sent to BD school in 7th grade, and expelled 4 times in high school.

To her credit, she was able to use the situation to make friends of all of my friends, and use them to control me. They would do whatever she wanted because they didn’t want to lose their invitation to the party. If she didn’t like someone she would turn the group against them. She knew everything I ever did, too.. She was like a mob boss, who’s only purpose in life was me. …And she was right about sowing my wild oats – by the time I was 18 I was pretty over partying. Didn’t care much for most drugs anymore, was tired of chasing ass and just wanted a real girlfriend, etc. And went into said relationship with ample experience for my age…

I ultimately got an engineering degree and will have been married 16 years in 4 days. Live a nice, quiet middle class existence,” one guy shared.

4. Enabling Substance Use

Not my parents (who were moderately permissive), but had a friend in HS whose parents would get high with him, supplied his younger brother alcohol and Vicodin on request, etc. Fast forward to today: both have major addiction and self-medication issues. Anecdotally: you can be a chill parent, but don’t enable and encourage your child’s substance use,” one individual cautioned.

5. Satisfying a Crab Cake Craving

“Upper middle class upbringing here. My parents got me a car and didn’t give care about what I did as soon as I got my license. I once drove 150 miles to Baltimore after high school one day to get some crab cakes,” one guy remembered.

6. Having a ‘Sober Babysitter’

“I wanted to try mushrooms when I was about 16, I told my mom and she agreed to trip sit me- basically, let me and my friends do mushrooms in the living room. She helped us steep it into tea, and then once we were all gone, she carefully timed her steps and ordered a pizza, baked cookies and watched movies with us, making sure everyone was having a “happy hippie trip”.

To this day, my mom advocates her “happy hippie trips” of doing drugs with a sober babysitter. I’ve now moved out, I do smoke cannabis with prescription, but I’m a rather functional human being with no party drive, but a deep love of quality time with my mom over a pizza,” one guy reminisced.

7. No Weekend Bedtime

“From the age of 15 I didn’t have a time that I had to be in at on the weekends. I would stay out until 3 or 4am drinking on the streets with my mates, come home and go to bed. Not a word would be said to me the next day by my parents.

When I was 16 myself and a group of my mates decided to get the boat from Ireland to Wales and get a train up to Manchester to see if we could score some football tickets. We left on the Friday morning and didn’t come home until the following Monday My mum called me on the Sunday asking me where I was, I told her I was “at the football” and she said enjoy, that she wasn’t putting a dinner out for me so,” one person shared.

8. Experimenting With Life

“I had crazy arbitrary rules growing up, but my friends always insisted i could do whatever i wanted. The biggest was that i was allowed free range to try new things. Want to make cookies from scratch, having never even seen it done? Give it a whirl. Want to make an entire lean-to survival shelter from things you get out of the woods? Watch out for snakes and be careful with the machete.

Want to ramp the road by the railroad with your bike? Listen for the train and pay attention to traffic. I was allowed to make a mess, get hurt, make my own fun from an early age. It was pretty great,” one guy shared.

9. Getting An Introduction to Alcohol

“My mom was worried I was not getting drunk with my teenage friends (we’re talking age 15-16). So she would gently coax me into drinking, offer wines to taste and to make me cocktails to get used to the taste of alcohol, and so forth. I never took up drinking, despite all her efforts. I grew up as a straightedge designated driver.

Also, starting Junior High she told me “you can skip school if you don’t feel like going. But only a couple days a year”. I ask her “can I carry those days from year to year?” she told me “sure”. I ended up never skipping a single day of Junior High or Highschool. :-/ That lady knew what she was doing, let me tell you that,” one girl shared.

10. Sleepovers With Boys

“When I was a younger girl, most of my best friends were boys. Mom constantly allowed me to have sleepovers at these boys’ houses. Guess what happened? We’d stay up all night playing video games and watching movies. /shrug,” one girl recalled.