With Valentines Day less than a week away, we’ve decided to run a little contest. The prize: an Iris Pleasure Object by LELO. The challenge: to submit your most embarrassing Valentine’s Day story– you can redact or change names if you want, but give us something that will make us cringe. On February 14th, Josh, myself, and Carmel the Intern will pick the most embarrassing tale of ‘best intentions turned worst nightmare,’ at which point we will priority mail the prize to the winner in hopes that it will help the poor sap out. The Iris boasts powerful and pleasuring performance through a pair of individually balanced vibrator engines that operate in harmony with each other. This contest is open to guys and gals– have fun with this one!


Justin Thursday, 02.08.07 @ 4:53 pm

At first, I didn’t remember that this was a Valentine’s Day story, but when I saw the phrase, “best intentions turned worst nightmare”, I not only remembered, but I knew I could win this contest.
You see, this happened in high school, some 15+ years ago. I swear every part of this story is 100% true.
I was a timid, awkward teenager, but this was my senior year and I had started to become a lot more social. I had a lot more friends that year, but I was still very shy when it came to girls. One girl in particular caught my eye and I admired her without ever saying anything to anybody about her. Her name was Erin. She was a smallish, fair complexioned Irish girl and my way of getting her attention was quite the machination.
I devised the plan after seeing a hallway sign for our school’s Valentine’s Day Dance. I thought about the impossible feat of Erin and I becoming the Valentine’s Dance King and Queen and I suppose you can say this is where the trouble starts. I scoped out the ballots and voting boxes and realized how easy it would be to stuff them! In true deviant teenager fashion, I was at the copier, copying off ballots, in about 30 seconds after devising this plan. I was trying to be careful, so I only put in about 25 votes for Erin and myself. I didn’t want to get caught, but with 25 or so ballots in, I didn’t really think that it would work either.
So, a week or so later, with this scheme already out of my mind, my friends and I were at Erin’s house having a party. We were having a great time, smoking, drinking, and whatever else we were told not to do by the adults. Sometime during the evening, Erin received a phone call from a friend, who told her she won the dance queen contest but she had to be there to claim the throne. Miraculously, there was no mention of yours truly on that phone call.
So, Erin and her giggly girlfriends were obviously excited. They were running around, getting her spiffed up and trying to get her to the school auditorium as fast as possible. We actually all went, everyone wanted to be there for her big moment. We piled in to a couple of cars and sped off.
When we got to the dance, they were minutes away from the announcement and we all came in as a group. The music stops, the lights go dim, the Student Council President comes on stage, “Our Valentines Dance Queen is….”
[uber-popular, snobby, socialite, cheerleader, very hot] “Julie.”
Oh crap. Erin runs out in tears. Her friends follow her. She is, of course, devastated after getting her hopes up. Or maybe she thought she was the victim of a joke. I didn’t really notice because seconds later came the results for the King….
Me.
(Uh-oh.)
While I am dancing with the cheerleader, who is completely and utterly disgusted with me and the fact that she has to dance with me in front of everybody, I can’t believe what is happening.
I was shocked and dumbfounded. I guess I accepted the crown because I couldn’t pass up an opportunity to buck the system, to shake things up so to speak. I probably shouldn’t have accepted. But when we all showed up to the dance, somebody noticed that I was there, but didn’t see that Erin was also there.
The plan worked! I stuffed the ballot box! They fell for it! and Erin loves me and thinks that I did the most romantic thing in the world for her!
Not exactly.
Erin was an emotional wreck. Seeing me win just made things worse. The party was a bust, and I never told Erin about my intentions, or the scheme, for fear she would blame me.
The school year would be over in a few months, and we were all off to college. I never let her know I liked her, and I never saw her after high school.


Erin Monday, 02.12.07 @ 1:04 am

You do realize that the vibrator prize costs $134 USD?!? That’s a lot of value for a story about how Single’s Awareness day can be shitty for most.


Funny MySpace Pictures Monday, 02.12.07 @ 5:58 pm

Freshman year of high school… I was super shy. And this girl in my homeroom kept looking at me. Every day she’d be looking over at me and every day I would sweat, trying to summon the courage to get up to talk to her.

Finally, on Valentine’s Day I bought a little stuffed teddy bear and wrote her a poem. In homeroom, I got up to give her the gifts… but when I sat down next to her, she didn’t even look at me.

She kept looking over in the direction of my assigned seat… that was directly below the clock.


Justin Wednesday, 02.14.07 @ 10:23 am

What happened to the story I posted last week?
I e-mailed about it and didn’t receive a response.
hmmm…..
Please explain!
Thanks! :-j.




Sponsorship:

Joshspear.com brings a dedicated, young, and influential audience to brand advertisers.

Please contact us for more information.

Regular content continued below...





Four Seasons Jackson Hole
Quackie Kids Storage
HERE Film
Teenage Engineering Updates
SOPA Time
SIHH 2012: IWC Top Gun Launch
Me-lo-dy Musical Airport Floors
Obliteration Room
My Year In Cities: 2011
GoDaddy Debacle