The worst Truth or Dare game I ever played

An embarrassing naked dare story

An embarrassing naked dare story

(Photo from MONOKO)

This story goes back to when I was a freshman in college living in the dorms. I was young, innocent, and excited for what college life had to offer. I felt the need to get to know as many people as I could and do whatever it took to be accepted. As a result, I was very susceptible to playing revealing games such as "Truth or Dare" with people I barely knew. Little did I know, my poor decision to choose the dare option would haunt me for the rest of my college career.


It was a Friday night of the second or third week and my roommates Phil and Sean, like me, were stuck in the confines of the dorms because none of us had cars. Alcohol was a commodity we did not have access to because we were all 18 or 19 and had not developed any personal relationships with upper class men yet. Rather than stay in our dorm room, we decided to venture out into the common room to see what our other suite mates were up to.

truth or dare stories a half naked guy
(Photo from CatherineSherer via flickr)

We were immediately greeted by high-pitched laughter and jubilant conversation from the others as they were all sitting in a circle around the main table; they were obviously playing some type of game. "You guys want in?" Katrina, a girl from the suite across, asked us convincingly. I looked at Sean and Phil who both looked at me nervously, and blurted out "Why the hell not!".

To this day I wish I would have never uttered those words. We joined the circle and were immediately inducted into their game of "Truth or Dare". At that point, I thought nothing of it. This was a dumb game I had played throughout my juvenile years that usually resulted in someone wearing boxers on their head. I was one of those people that would always stick to "truth" anywas because I didn't have that colorful of a past so admitting to anything was not incredibly embarrassing.

There were four others in the circle, not including me, Phil, Sean, or Katrina. They were two guys and two girls whose names escape me. The game resumed and Sean was the first to be asked "Truth or Dare" by Katrina. Sean safely chose "truth". "How many girlfriends did you have in high school?" she said on the verge of laughing.

This question was comical in the sense that Sean was an obvious nerd that had never been in a relationship or held more than a 10 minute conversation with a girl. "Zero" he answered half ashamed, half embarrassed. I quietly laughed to myself. The game continued on for another thirty minutes with everyone choosing truth making it incredibly boring and uneventful. Eventually, I decided I was going to choose dare because I was over it and wanted to leave.

One of the girls asked me "Truth or Dare?" to which I immediately responded "DARE!". Everyone was obviously surprised. Some background information to my school: I went to a college in San Diego, CA located right next to the ocean. Our dorms were located at the top of a hill with a path that led down to the local Blacks Beach.

This beach is a half nude and half normal one with the two sides being separated by a line of traffic cones. "I dare you to run down the hill in your boxers to Black's and bring back one of the traffic cones!!!", she uttered hysterically. "crap..", I thought to myself. I had really set myself up for that one. The hill was extremely steep and considerably dark at night. The beach would be even darker because there was no moon out.

Knowing that this was going to be an adventure, I stripped down to my boxers in front of everyone without saying a word and took off to the stairwell to make my way down to the beach. It was extremely cold and moist outside making it hard to keep my eyes open. I ran across the street and along the beach path until I reached the top of the road down to the beach. I began sprinting down it to keep my body temperature up.

After a 15 minute jog, I had reached the base of the hill and felt the cold sand lodge itself between my toes. The divider line between the beach sections was another half-mile down. I could not see anything except the black outline of the ocean thirty feet away. I started running again, hoping I would see something that represented a traffic cone. Eventually, I finally found the line of cones after nearly running into one.

At this point I was panting and all I wanted was to be back in my room passed out. I grabbed the stupid thing and began running back to the hill. I finally made it up the hill to the street with the dorms on the other side. I crossed it and just when I was about to reach for the door to the stairs a flashlight suddenly blinded me accompanied by the words "What the hell do you think you're doing?".

It was a campus security guard and from his tone, I could tell he was extremely pissed off. He grabbed the cone and began asking me for my information. I heard murmuring and echoes of laughing from upstairs. Everyone was watching me get written up from the common room window. "This was a horrible idea ", I thought to myself with regret.

30 service hours and four years of college later my former roommates and suite mates still bring up that night whenever I bump into them or talk to them on Facebook. I had to take the cone back to the beach the next day and meet with the disciplinary provost to talk about respecting San Diego's beaches. I will never forget that night of eternal embarrassment.



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Jan 21, 2012
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Nice one
by: Ben, the daredevil

Haha. Awesome story, bro!
You know, if you really wanted to get back at the girl who dared you, when she said "get the cone in your boxers" you should have said "Fine...but you're coming with me...NAKED!"
And eventually...on the beach...those boxers would have come off and you would've had the best night of your college life.

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