We all grow up with a certain level of protective sheltering in our lives. Whether it was intentional, on the part of a well-intentioned parent, or a complete display of ignorance there usually comes a time where we need to flee our cocoon, and that's when we are most likely to find others that leave us scratching our heads. Or maybe you're left scratching your head at your own naivety. Whatever it is, it can make for some pretty awkward and funny moments, and we've compiled some of the best of these stories below. Enjoy!

Want to read more? You can find the source links at the bottom of this article. 

I have a friend whose parents are super controlling. When he moved to the states without them his dad set up security cameras outside his house. We were hanging out after work (only until like 6 or 7 pm) and his dad called freaking out because his car wasn't in the driveway yet. He is 28 years old.

DemelzaR

I was ushering my class outside for field day, and everybody is joking and having a good time, when suddenly I hear "You Dildo!" I pull the culprit aside and ask them if they knew what they were saying. They said they didn't know what the word meant, and I believed them - a lot of kids that age parrot what they hear without understanding the meaning. So, not wanting to ruin the kids's day, I talked to them about not using words we're unsure about, and had him sit out of the first two activities. No biggie, problem solved.

We're having fun with the class when the principal walks up. The principal had been talking with the kid, and asked me why the kid was sitting out. I explained the situation, but the principal still didn't understand what the problem was. The principal thought dildo was referring to an armadillo.

Yup, I awkwardly explained what a dildo was to my principal.

Nemesys2005

Guy grew up in Utah, and never left Provo until his mission. Met him while he was a missionary in Japan. He saw someone standing in front of their house smoking a cigarette and said to me "That would never happen in America."

otakufish

My friend online asked me to explain what sex is.

He meant to ask what the difference was between males and females.

He was horrified that I had suggested putting a part of his body "especially one so private and reserved for God" (still not sure what he meant by that) into another person.

I eventually learned that he was not aware females had periods either. After explaining that one to him, he vowed "I shall always be nice to women, especially when I know now that every time they are being witches it comes from the hurt inside." He then decided the cost of chocolates was "not so unreasonable, considering what it is good for" (soothing females on their periods). 

AprilSpectrum

This is a combination of sheltered and spoiled, but once someone spilled water all over my laptop and a girl who was there saw me freaking out and said, "Geez don't get so upset, seriously, just tell your dad to buy you a new one. My dad's bought me like three."

idgapho

Try dating somebody who grew up in a vastly different socioeconomic class than you.

I grew up on a first name basis with the food bank people, my ex grew up next door to a guy who played for the Dallas Mavericks. There were many head turners she popped off over the 2 or so years of that relationship, but my personal favorite will always be her absolute incredulity that I never visited Europe during high school. But baaaaabe, everybody travels for summer at that age! No. No we do not. Babe, wait until you see the picture of the death trap I bought with cash I made working at Jack in the Box over that summer you spent prancing around Scotland. You'll be terrified I ever intentionally drove that thing.

slowhand88

My young daughter, upon finding out babies happen because of sex, looks at her sister, looks at me and my wife, does some thinking and says "So you guys have had sex twice!?"

We busted up laughing.

KaJashey

I was a very 'poor' kid with a scholarship to one of the richest if not THE richest high schools in the city. I have quite a few gems.

This one boy who's dad owns about 15 Ferraris was talking to me about life after school (he was 17/18 at the time) and I said I wanted a studio apartment. He thought it was a whole floor to yourself. When I explained it was just one room, he was confused for a long while, thought I was making things up, and when he eventually accepted it said, "why would you want to live in something like that? It's pretty much a jail cell isn't it? I can't believe poor people live like that... do poor people really live like that?"

I went on to explain to him that actually poor people are a lot worse off, you still need quite a bit of money and solid savings and income for a studio. For some reason he thought the smart thing to spew out of his mouth was, "you know, I heard when poor people feel sad about being poor, they watch documentaries on Africa and stuff like that. Maybe you should try that sometime." He was genuinely 100% serious and thought it was good advice. All I could say was, "thanks, I'll try that next time!"

There was also the time I was stuck in a global politics class where no one knew what welfare/the dole was. The teacher explained, and everyone was OUTRAGED because why should lazy poor people get THEIR money that they worked hard for? How dare they not work for it like rich people had to. My family was on welfare at the time, both my parents were made redundant around the same time because of budget cuts. I was 15 and the only one in a house of 6 people with a job. Welfare helped us eat. It took all my strength not to break down in tears during that class, indirectly hearing that I'm scum and don't deserve to eat, pretty much.

They'll do anything to show off how they donated $20 to a charity in Africa, and rave on and on about third world countries, but when it comes to fixing our own they don't say a word or they criticize the less fortunate because their money is more important than the people.

pixiebch

My friend, at age 23, believed his old pets were still living away on a farm somewhere. Including his parrot.

andygra

"What feels so great about someone blowing on your penis?"

stapletheeyes

One of my wife's friends said she'd never send her kids to public school because there are gay and lesbian students there. The private school she sends her kids to has two lesbian and one gay teacher.

SilvrSurfer

"I wish we had nice things...."

As he was seated on his father's 30 foot boat.

CHungry4More

"I don't even want to travel outside of the U.S. Its all so dangerous and ghetto."

totes-muh-gotes

My coworkers were talking about reality TV. One of them said something like, "Did you hear about that child beauty pageant show? Apparently one of the moms dressed her little girl up like a prostitute! And the judges all thought it was great!"

No one could remember the name of the TV show, so my coworker said, "Oh, I'll just Google 'little girl prostitute video'..."

I had to explain to him why that might be a bad idea.

(If you're wondering, the show was "Toddlers and Tiaras", and the girl was dressed as Julia Roberts' character from "Pretty Woman".)

captainmagictrousers

One of my very affluent friends said that they are "working class" because her parents still have to work rather than living off of stocks/interest/whatever people with "old money" do.

allisonwonderland00

I worked with a girl that went to a large suburban high school (~4500 students). She tried to tell me that her school didn't have any pregnant girls or students with drug problems, but my mom was the school's nurse. There were around 40 girls in her grade alone that were pregnant, 4 of whom were having their 2nd kid. She was also shocked when I told her that there were a lot of kids with drug related offences on their records, some had heroin addictions, and I showed her news articles of major drug busts at her school.

surveyor_of_land25

"Are you from Africa?" "What's it like in the ghetto?" First day of 5th grade, after just moving to Florida.

wulf_titan

Working in India. I had a coworker who was from a very wealthy family in the States. Lots of issues, but one that sums it up well is that he believes the sandwich shop in the cafeteria 'hooks him up'. No Greg. There aren't lines or order here. You have to pay after you get your food. You are just taking the food and not paying. No random Indian who has never spoken to you is so enthralled with your charm as to give you free food all the time. He just has no real recourse to complain as he is paid probably around 5 USD a day and doesn't feel comfortable complaining about a white employee who makes more than 80% of the people in the 14flr building. Start paying the 35 Rupees for breakfast, you brat. It is like 50 cents.

tristanjones

Yesterday my 24 year old female coworker asked me what a clitoris is.

katiebug88

From someone who grew up about an hour away from London, "Are there more than 2 train stations in London?"

Same person said "You could wear me as a hat" and didn't understand why everyone found it funny.

She also hadn't even seen a photograph of a penis until she was 20 and didn't know if the balls were above or below the penis.

Her parents wouldn't let her see her friends unless a Christian went with her, because her dad didn't trust people who aren't Christians. In England this basically means he can trust about 5 people under the age of 30.

BoxOfNothing

My ex and his family were confused to find out that I kept my pet cat inside and not tied to a tree in my backyard. They even offered to buy me supplies to do so. They couldn't understand why I would ever let anything like that live in my house.

robinreddress

My sister's house-mate is from Cambridge. When I went to stay with them I got to see her try and make breakfast. She couldn't work a toaster. She didn't understand pre-sliced bread. She couldn't crack an egg. She woke me up to crack eggs for her. Which she then didn't know how to scramble. She asked where the olive oil was, because she wanted olive oil for her toast. Alziari olive oil, which is around 3 for 100 ml. We only had Asda's own, and when I told her to use that, she lay down on the floor and sobbed that she, "just couldn't take it anymore!"

NaNowhyMo

Rich girl I dated in college. 

Her - "My washing machine is still broken, what am I supposed to do if the apartments don't fix it before I run out of clothes??" 

Me - "Do them at a laundromat." 

Her - "Those aren't real. " 

Me - "...what? What do you mean?" 

Her - "Those are just something in old movies." 

So I drove her to a laundromat that was a few blocks away from her house. She laughed. I laughed at her and quietly wondered what I was doing with her. A few days later she asked me, "Why do they even call it olive oil? There aren't even any olives in it." Not the brightest girl ever, but she actually was very fun to be around.

Rustyshaklford

Stories from this girl are more or less how I have all my karma. Here are a few pearls of nonsense that have flopped out of her face.

"It's not sex if he uses a condom."

"I had anorexia! When I had flu I didn't eat for like two days!"

"I'm allergic to sugar!" She lives off bread and drinks neat vodka regularly because it's not overly sweet, so it doesn't have sugar in. She would also insist on eating some cake or fruit I was eating and then make gagging noises and say how awful it was.

Acyts

Not something they said, but I had a home-schooled friend who's father completely controlled him, and didn't allow him to have real life friends. He controlled who he talked to when playing online video games.

Our fathers worked together, and eventually we became friends, playing games online together. At one point our parents agreed we should meet up and hangout in real life. First time he came over I wanted to show him my computer in my basement, both of us around 12, I head down the stairs and turn back to see he didn't follow me. He then plumps his butt on the stairs and does that all the way down the flight of stairs.

Over our about 2 year friendship this never changed. Still talk to him via steam but no idea if he is still this way.

Pgaylolol

My ex went to bible college. Her roommate was part of a "I'm not doing it!" group that performed vague skits about abstinence. She was kicked out because the baby bump she had became pretty obvious. Her boyfriend insisted they never did it. They eventually found out that she let her previous boyfriend do things that she didn't understand. Those two had a shotgun wedding days before the baby was born. Her mother had told her that babies come from seamen, and being from Nebraska she was far from any sailors. I wish that last sentence was a joke.

DarrenEdwards

Guy I know was talking about how New York City was the worst place he'd ever been to.

He'd been to the LaGuardia airport. His connecting flight to Aruba was delayed overnight. This was the one time he's been to New York City.

Barkingpanther

I have a friend from a super-wealthy background who doesn't really understand things like frugality, because he's never had to be frugal himself. And he seems genuinely surprised by people who live less extravagantly than he does. It's all 'this is the lifestyle I like', which is basically expensive wining and dining, all the time. Like he's entitled to live a life of leisure without working hard in order to afford that lifestyle.

He's one of those people who just pisses away money and expects people to give him money when he hasn't got any himself.

He's had jobs here and there and he actually has a bachelor's degree too, but he's never not had his parents paying his rent for him and giving him an allowance, and seems to have zero desire for any kind of career. He's 27.

ioncehadalife

"Rent is what, like $30 a month?"

Entegy

My old roommate brought over a girl he was dating one summer day. I was outside mowing the lawn when they pulled into the driveway and they walked over for a quick introduction. The first thing she said was "What are you doing?" I thought it was just like a rhetorical question so I just responded with "Haha yeah it's pretty hot out today." But then she asked again, so I said "Ya know, just mowing the lawn." She was really nice and everything, but the look on her face was like when you explain something to a kid and they say "Oh okay" but on the inside they're trying to wrap their head around this wild new information you've just given them.

JaceComix

My old roommate and I about a year ago were joking around about how female roommates use more toilet paper, and he started to get genuinely annoyed. He started saying stuff like "What the heck? Why do they use so much more? I don't get it at all, it's just rude!"

Had to explain to this 28-yr-old that women generally wipe when they pee.

TerraAdAstra

A woman I went to undergrad with didn't understand that you have to pay credit card companies back because her father paid her balance every month.

worksafemonkey

Thanks for reading!

Sources: 1, 2,3