People tell us

People Tell Us About the Worst Things They Did On a Dare

Sometimes it's good to be a truther.

by Justin Caffier
08 November 2017, 3:36am

Vice President Mike Pence touches a piece of equipment labeled "Do Not Touch" after being dared to do so by Florida Sen. Marco Rubio during a tour of Kennedy Space Center. Picture by REUTERS/Mike Brown.

Kids are easily manipulated. They'll do just about anything you ask if you frame the request as a dare that challenges their fragile, budding senses of self worth. Sometimes, these challenges get a bit out-of-hand, other times, they can have truly tragic outcomes.

Dares can be character-building experiences in one's formative years, however. The sobering rush of pain or embarrassment that comes from completing an ill-advised dare is often a catalyst for youngsters realizing that maybe they shouldn't just go along with what any old asshole asks them to do as they go forward in life.

We asked people to dredge up the past and divulge the worst, cruelest, craziest, and otherwise most regrettable dares they went through with.


Back in the fifth grade, someone dared me to scrub a Teddy Graham off the bottom of my shoe and eat it. Now, in my young mind, I was indestructible. Plus, there was a girl right next to me that I really wanted to impress. Using my imbecile fifth-grader logic, I scrubbed the graham off the shoe, ate it, and came down with a 106 degree fever. The next couple of days were a blur. I haven't taken a dare since.
- Kevin, Los Angeles

When I was young, a friend dared me to stab beneath my frenulum with a sewing needle and thread string through the hole, the goal being to then pull the thread and stretch my dick out longer. It was painful as hell and, of course, did not affect the length of my penis.
- Anton, Mexico City

I bought some cock-numbing spray (supposed to make you last longer) at an adult store in Guam before heading to a brothel my friends were taking me to. They dared me to jack it to see if the spray worked, so I jacked in a taxi full of people. I'm not sure if the numbing spray worked or it was stage fright. Not my proudest moment.

- Eric, Hoboken, New Jersey

I visited LA in my early twenties and was an audience member at a Jimmy Kimmel taping. Justin Bieber was the guest but I wasn't really familiar with him at the time. My friend dared me to act like an insane fan of his and outdo all the teenage girls in the crowd. I went so ballistic when Justin came out that Jimmy called me out on camera.
- Patrick, Los Angeles

I made out with my sister. We never spoke of it after.
- Stefanie, Las Vegas

I'm ashamed to admit this but, at a summer job when I was like, 15, my friend dared me to sleep with one of our coworkers who we both thought was pretty cute. To make matters worse, I was completing this dare for the measly sum of $10. To make matters even worse still, once I'd gone through with it and seduced and slept with her, I was dared to, for another $10, tell her that the entire thing had been nothing but a game. I did that too.

I felt so terrible after and I think that was a catalyst for me growing up and trying to be less cavalier with romantic partners going forward. I never got to apologize to her so, if you're reading this, I'm so sorry. That was incredibly shitty of me, my age is no excuse, and I hope it didn't fuck you up too bad.
- Sean, Pittsburgh

Photo courtesy of Ryou

About ten years ago, I got into a fight with my ex-boyfriend and he locked me out of his apartment. I was texting my friend about it while it was happening and this friend dared me to pee through the key hole to get back at him. But the key hole was too high, so I wound up squatting and aiming the stream of piss at the gap between the door and the floor.
- Ryou, Tokyo

The entire party had been spitting its chewing tobacco into a Mountain Dew can and, for only $5, I took an enormous chug of it and swallowed. I spent the rest of the night vomiting on the driveway.
- Chris, Tempe, Arizona

Photo courtesy of Taylor

My relationship with my boyfriend was going down the tubes because he'd stopped having sex with me so, to spice things up, while I was high on ecstasy, I thought it'd be a good idea to send him a video of me eating a friend out in a Vegas club bathroom. Apparently that was the wrong move and things unraveled from there.

He broke up with me a few days before my 21st birthday. We'd had tickets to see Blade Runner on some rooftop but, because that was no longer on the table, I instead got drunk with a good gay friend of mine and we decided to get tattoos. Turned into him ending up with a bee and me getting dared to just get this classy, fun, timeless one to commemorate the series of events.
- Taylor, West Hollywood

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