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Reddit User coolsexguy420boner Claims He Took Kate Upton To Homecoming In 2007, Shares Photo

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***** UPDATE: Turns out it was a joke. *****

coolsexguy420boner made the story up, but we have located the real guy in the photo. A possible interview upcoming.


Reddit user coolsexguy420boner has a hell of a story to tell about the fall of 2007. It was back when he had braces, and back when he outkicked his coverage by a hundred miles with a tall, blonde bombshell named Kate who wouldn’t give it up to him. It was also back before that same tall, blonde bombshell named Kate who wouldn’t give it up to him became an international superstar who boasts possibly the greatest set of natural Hindenburgs on the planet.

He posted his story on Reddit, along with this photo that he claims is from his homecoming dance in 2007:


After asked to share the details, coolsexguy420boner shared the following:

We met early in highschool at volleyball practice and through some mutual friends. We “talked” for a little while and started dating a few weeks after that. No I never “banged” her, I was like 16 years old and her family was really religious and it never really got that far. She was a really cool girl but I broke up with her because her family made it impossible for me to get close with her and it was hard on both of us to get a real connection.

I had no idea she would become an internationally published model one day, but that doesn’t really affect the way I feel about her. [sic]

The comments, as you can imagine, are hilarious:

Screen Shot 2014-02-19 at 11.30.52 AM

I want more than anything to believe coolsexguy420boner here. On one hand, coolsexguy420boner seems like a straight shooter, even with his black dress shirt. He’s got an honest face and a shitty tie knot that says he doesn’t take things too seriously. On the other hand, this story, while not outrageous, is tough to buy. How can we be so sure the dude pictured here is coolsexguy420boner? It’d be easy to track down a rare, old photo of Upton from high school and claim to be the asshole who was lucky enough to make his way into the frame, wouldn’t it?

Don’t let us down, coolsexguy420boner.

Screen Shot 2014-02-19 at 11.46.47 AM

And, as promised with every Kate Upton piece I write, here’s your gif:

[via Reddit]

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Dillon Cheverere

Dillon Cheverere (@DCheverere) is the Vice President of Media for Grandex, Inc. Email:

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