The story of a guy who went to homecoming with Kate Upton…then broke up with her

Douglas Charles Managing Editor

redditor kate upton homecoming The story of a guy who went to homecoming with Kate Upton...then broke up with her

coolsexguy420boner, Reddit


Redditor coolsexguy420boner (sweet username) told a story yesterday about how he dated Kate Upton in high school, even going to homecoming with her, but later broke up with her. Talk about your all time errors in judgement. Here’s his story. (By the way, that’s them at homecoming in the picture above. Damn.)

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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.

I think the Reddit commenters speak for all of us…

tobyqueef: you. broke. up. with. Kate. Upton….let that sink in.

Elijah6053: Is it weird I am actually almost crying for this guy. Crying for the guy who broke up with Kate Upton. That’s manly right?

TheEternalWoodchuck: Holy shit. coolsexguy420boner is has literally dumped a hotter girl than any of us have ever had. Fuck. fuck.

Yes, no matter how insane his decision to break up with Kate Upton back in high school seems to us now. TheEternalWoodchuck said it best. Man deserves some props.

And as Captrotc put it: “coolsexguy420boner has proven quite conclusively that there is not such thing as ‘out of your league.’”

Words to live by.

UPDATE: The asshole lied about the whole thing. Damn him.

Want more Kate Upton news, pics, videos, & GIFs? Just click here.

Me and Kate Upton before homecoming 2007 [Reddit]

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