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What’s the Sneakiest Thing Your Teenager Has Ever Done?

One day they’re an innocent, apple-cheeked, sweet toddler, or an artless elementary school student who wears every thought and emotion on their face. Then suddenly, you find out your teenager has been lying to you—regularly, smoothly, convincingly.

It’s a moment for which few parents are prepared. But in retrospect (and you’ll have to take our word for it), we at Your Teen actually have fun swapping stories about the sneaky, devious or deceptive things our teens did. What is the sneakiest thing your teenager has ever done?

Our Teenagers’ Sneakiest Stories (That We Know About)

This didn’t happen to me, but it’s so sneaky I am in awe. I have a friend with a daughter who is 15. Homecoming was coming up, and my friend is kind of a stickler for modest dress. She told her daughter that her dress had to be knee length, and she had to see it on her to approve it.

The daughter ordered the dress, modeled it, and received her mother’s approval.

The night of homecoming arrived, and the teenager came downstairs for photos and to meet her friends. My friend was surprised and shocked to see how very far above the knee the dress was. “Wow, honey, you must’ve really had a growth spurt since you ordered that dress!” But it was the day of the dance and there was nothing to be done, so off to Homecoming she went.

The next day, my friend was again marveling at how much her daughter had grown in a few short weeks. Then her daughter fessed up:

She had ordered two different sizes of the homecoming dress and tried on the larger size for her mother to approve, but then wore the shorter one to the dance.

My own kids? One son wet his toothbrush for months without actually brushing his teeth. My daughter apparently wore a Sex Pistols t-shirt under her school uniform shirt for months. Then there was the St. Patrick’s Day parade where one procured Hard Mike’s lemonade for his sister and her friends. They’re in their twenties now, but I’m still too scared to ask for the really sneaky stories.

Jane Parent, Senior Editor

My naivete has been shot to hell. Group text. “What did you do in high school that we don’t know about?” Until five minutes ago, I would have said no way.

But apparently, we hosted an after-after-prom in our house with drinking in our basement.

We were home. We were asleep. We never knew anything.

Susan Borison, Editor

My son was a freshman in college and home for Thanksgiving break. He was headed to a friend’s house to meet up with all his high school friends. I told him we’d be happy to drive and one of his older brothers would pick him up just in case there was drinking, and he wanted to have a beer. I drove him to his friend’s house and as he got out of the car he said, “Thanks Mom, and can you pop the trunk?”

So I did, and then watched him walk past me with a case of beer.

Thanks, older brothers, for the purchase and the ride home.

Mindy Gallagher, Social Media Manager

My daughter and her three friends, who were spending the night, wanted to TP someone’s house. I said no because it was after curfew.

They set alarms and snuck out of the house at 5 a.m., after curfew was over.

When caught, she said they had not broken curfew. Semantics!

Eca Taylor, Circulation Manager

Like Sue, I am sure that there is a lot that I don’t know about, and unlike Sue, I am not quite ready to ask. My kids don’t seem to be so good at being sneaky, although I am sure they are. Once, my daughter texted to tell us she had a ride somewhere and promised that she would be the only passenger in the car with her friend (per the law in Ohio).

Then she posted a picture on Instagram which my son promptly showed me.

In his defense, I had already seen it. At the end of the day, we certainly had our concerns about her safety, but the bigger issue was the lying, and that is something that we spent a lot of time talking about. It was a very poor effort on her part, and I am grateful for that.

Jody Podl, Online Editor

Just last weekend, my son asked to go to one friend’s house (where the kid and parent were known friends) and instead went to another house.

Not sure it really counts as sneaky because he knows we use Life 360. It was more a case of “do what you want now, even if that means lying, and ask forgiveness later.” He came home completely wasted and confessed that he did not tell us where he was headed because he “thought we would say no.”

Just the week before, my daughter asked to walk to Starbucks. Life360 showed her walking past Starbucks to the house of a boy in her grade.  When asked, her twin brother chimed in to say that Life360 must have been “glitchy” that day. Only when I confronted her with the fact that the friend she was with had ‘fessed up to her mom would she admit she lied to my face multiple times.

In a much more innocent time, my twins once snuck each other the answers for each other in the eye doctor’s office because my son could see the eye charts and my daughter couldn’t.


My son’s friend put his regular phone in his locker after school so that his parents would think he was staying after for practice/homework/club.

He got a secret burner phone to use for talking to his girlfriend. He spent afternoons with his girlfriend having sex, drinking beer, and smoking pot (and posting about this on social media, which is how his parents found out what was going on).  They ended up installing a secret tracker in his car so they could see where he actually was.

He’s now happily and successfully at a four-year university, having outgrown this sneaky stage.


In middle school, the group chat entered my daughter’s life.

We found out she was up ‘til all hours contributing to a group chat with dozens of kids at school.

We told her she could not use her phone after she went to bed, and that we would take it away at night if she couldn’t abide by that. (In hindsight, it should always have been the rule to dock the phone in the kitchen every night, but she liked using it to listen to music to fall asleep and to set her alarm to wake up in the morning, and we wanted her to learn to self-regulate her cell phone use.)

Of course, she couldn’t stay away from the group chat—surprise, surprise—so we decided to cut the Wi-Fi off for our entire household at 11 p.m. every night. This caused us inconvenience, and she protested that she sometimes still needed it past this hour for homework. But we stayed firm and told her to plan ahead. We thought this solution was working well until she much later confessed that she had rigged up her own hotspot. Teen: 1, Parents: zero.


Jane Parent, former editor at Your Teen, is the parent of three.

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