Unbreak My Heart: A Retrospective Of Jay Cutler And Kristin Cavallari

Senior Writer
07.25.11 5 Comments

Less than a week after we learned that we could buy a $2,800 knife set to show our appreciation of their love, the engagement of Jay Cutler and Kristin Cavallari is no more. According to various, terribly-written and misleading tabloid reports, Cutler broke up with the former star of The Hills.
According to People, this is possibly the worst thing to ever happen to anyone. Ever. In the world.

“She got dumped,” says another source. “She’s absolutely devastated. She can’t believe this is happening.”
“She was planning her dream wedding, the date was set, the location – everything was set,” the source says. “She’s in shock that the dream wedding she was planning is going to end this way.”

Keep in mind, she doesn’t seem to give a sh*t about losing her man, she’s just apparently upset about the dream wedding going down the crapper. So why the split then, People?

“Jay Cutler was beyond controlling and didn’t really like Kristin to go out,” the friend says. “When she did go out, he called all the time and demanded to know exactly where she was going and who she was with.”
The friend adds: “He made her choose between him and being friends with a lot of her girlfriends. I’m not surprised it didn’t last.”

I’m not one for hyperbole, but this is the most shocking revelation in the world. On no planet, in no dimension, would I have ever imagined that a 24-year old party girl would cause her reclusive NFL star fiancé to stress out over fidelity issues. I bet it’s because Cutler didn’t trust that Justin Bobby guy. He was always up to no good.
This news really upsets me, though. I know that Cutler generally comes off as an apathetic, antisocial, malcontent jerk, but there’s still just something charming and affable about the overgrown frat boy. So I reached out to my good friend J-Cutty to see if he could tell me in his own words what went wrong with America’s sweethearts.

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Things started to go downhill when we first did our registry at Crate and Barrel. I was pissed they didn’t have a Jager machine, because Greg Olsen promised me one.

And she was all bummed about something, but I was like, “Do you see how sweet my sleeve roll is?” Took me 3 hours at a ‘Crombie & Fitch to learn that.

The tabloids say that we weren’t happy, but look at how happy we were. I think I told a funny joke from Maxim here.

But then the paparazzi were always following us and I was like, “Yo bro, no flash, dude.”

Sometimes we’d go out to eat and the waiter would make a comment like, “I see right through you” or “Your girl is wearing a black bra” and he’d laugh and I’d be like, “I don’t get it, bro.”

The camera guy was like, “I don’t know which is more transparent, the glass or Kristin’s see-through shirt” and she would laugh but I still didn’t get it. Not cool, babe.

Then she finally explained it to me.

I told that camera dude that I was gonna f*ck him up.

Kristin was like, “Cool it, J-Cutty,” and then I was totes happy. Even if her boobs looked weird.

I mean, look how happy we were, Browen Wilson. And it had nothing to do with her cans looking huge.

But she didn’t appreciate it when I was like, “Knock knock… who’s there? Not your ass because it’s missing.”

She also thought I was upset that she bought me a watch to match her purse, but I just love Sour Patch Kids.

And she always had dudes throwing their gunts in her face. It was bogus, brogus.
Sometimes we’d go to the pool and she’d be like, “Why don’t you take your shirt off?” and I’d be like, “I had a lot of dairy.” Chicks just don’t understand my pecs.

In the end, I was just like, “I love boning you, but I’m not in love with you. So peace out or whatever.”

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