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The Most Jay Cutler Thing That Jay Cutler Did on ‘Very Cavallari’: Week 5

In which Jay Cutler commits himself to a task. (The task is oral sex.)

Jay Cutler with a coffee cup E!/Ringer illustration

All this time we were trying to force Jay Cutler to be a great NFL quarterback, when really we should have been letting him fulfill his destiny as a perfect reality TV character. On his wife Kristin Cavallari’s reality show, Very Cavallari, Cutler uses his trademark quality of “not caring” to turn himself into one of the best comedic characters of 2018. Because it’s obviously completely necessary, from here on out we will be checking in on Jay Cutler’s non-antics on Very Cavallari, discussing his highlights and lowlights and best quotes, and handing out a weekly award for Jay Cutler’s Most Jay Cutler Moment. Let’s get to Week 5.

Important Question: Does Kristin Cavallari Like Jay Cutler?

I know Kristin Cavallari loves Jay, but I can’t be all that sure she likes Jay. So far on Very Cavallari, it has been made clear that Jay and Kristin live in two different worlds—Jay in a world of dead fish, goats, and deer with human names, and Kristin in a world of high-end jewelry and home goods. It has also been made clear that Kristin isn’t exactly thrilled whenever Jay crosses over into her world, which is the primary reason why she’s pushing him to get a new job after retiring from the NFL. “Just to not have to deal with Jay on a daily basis … I cannot wait for that to be over,” is something she actually said in the premiere episode. Then, on Sunday night’s episode, just before Kristin jetted off to Los Angeles to do E!’s Oscars red carpet show, this happened:

Not only is that a blatant “no” face; it’s also a “I’m almost laughing that you asked the question” face. “We’ve been together for so long, honestly it’s kind of nice to have a minute to myself,” says Kristin, a woman who has been married for only five years.

Shortly thereafter, Kristin ranks her life priorities thusly:

1. The kids

2. Work

3. Jay

Tough break for Jay Cutler! His streak of never being ranked no. 1 on lists continues.

This doesn’t make sense, though. Not just because Kristin is married to Jay, which would make you think she likes him, but also because, as we found out in Episode 5: Jay Cutler’s good at sex stuff now.

Jay Cutler’s Good at Sex Now

“The sex is the best it’s ever been,” Kristin tells her L.A. friend over delivery sushi. “He apparently read some article on GQ about how to go down on a girl … It’s been a game changer.” She then adds, “Yeah, like every time,” without being prompted in any manner, just so we all know the frequency with which Jay Cutler performs oral sex.

And just like that, Jay Cutler’s back, baby! While I’m sure Jay doesn’t love the idea of his wife talking about his sexual performance on national TV, on the other hand, the review is very positive, so maybe he thinks it’s awesome. (Truthfully, he doesn’t watch TV—he watches deer cams—so it probably doesn’t even matter to him.) What I’m most proud to hear is that Jay Cutler’s putting in that work, man. He saw an area needing improvement, so he did the research, started practicing, got serious about putting the necessary reps in, and ultimately turned a weakness into a strength. He has arguably never done this before, not even in his career as a professional quarterback.

And just so you know—it’s not just the mouth stuff. “The sex is also, just like, the best it’s been, too,” Kristin continues. “Like all around. Like, I don’t know what happened to him but it’s great. Almost eight years later, mmhm.”

Congratulations, Jay Cutler.

A Short Interview With the Woman Who Taught Jay Cutler Oral Sex

The GQ article in question, “How Real Women Want You to Go Downtown,” was published on February 23, 2017 and written by freelance writer Rae Witte. The anecdote regarding Jay Cutler’s “improvement” was included in the “This season on Very Cavallari…” after the first episode aired in early July, so Witte has known for about a month now that she personally affected Jay Cutler and Kristin Cavallari’s sex life. I called Witte, and we talked briefly about finding out this news, and what it feels like to know for a fact that you’ve improved a former NFL quarterback’s sex skills.

Tell me what it was like when this first came out. Did people start texting you and tweeting at you?

A total stranger tweets me and is like, “Thank you so much for this.” And he had done a thread and one of his tweets was like, “I need to find this piece that Jay Cutler read.” I’m like, “What the hell?” And then friends that follow Barstool started texting me, and I couldn’t help but laugh. My friends were like, “You helped a famous married couple!”

What does it feel like to know that you taught Jay Cutler oral sex?

I mean, I’m happy to see that it actually works! I did a lot of research—I talked to a ton of men about where they learned—and to hear that someone not only applied [my tips], but that he communicated to his wife like, “This is where I picked this up,” makes me so happy for them!

What do you know about Jay Cutler?

Um, very little. I know he’s a quarterback; I know everyone kind of, like, puts their hands over their faces and shakes their head at him? But that’s about it.

I ask because, no one would ever describe him as “communicative,” but one of the main points of your article is communication. So my question is: What the hell?

Maybe he’s a good listener. Obviously the overarching point is to communicate evenly, but a lot of it is about listening and asking and listening to what this person wants.

Well, Rae, those are my questions. Thank you. Kristin Cavallari thanks you.

Jay Cutler’s Quote of the Week

Listen up, jabronies. If there’s one takeaway from this episode, it’s that champions wake up early. Just ask Jay Cutler, who explained why he prefers rising at the crack of dawn:

Now there’s the look of a determined man. That’s a revved up facial expression that’ll really have you feeling inspired.

Guys Night With Jay Cutler

With Kristin in L.A., Jay Cutler has the house all to himself to throw a little guys night. This means a night full of man stuff, like drinking whiskey; grilling all sorts of meats—maybe even the elk meat from the premiere; and talking about “African Dwarf goats,” which Jay Cutler was considering buying before Tony, a man in a bolo tie and the one person on the planet who knows more about goats than Jay Cutler, told him not to. But really, here’s the manliest thing to happen during Jay’s guys night:

I’m gonna go out a limb here and say that Jay Cutler and his friends are eating steaks not with forks, but with CIGARS. That’s the most man shit I’ve ever seen. Who needs forks when you can just mash a Cuban into your porterhouse, amirite bro? (In a later scene, you do see someone using a fork, but let’s forget about that; this version of reality is way better.)

The other major thing to happen during Jay’s guys night is when the subject of vasectomies comes up and—BREAKING NEWS—we learn that Jay Cutler had a vasectomy. But not only that! We learn that the vasectomy may not have been Jay’s decision. First, Mr. Bolo Tie asks, “Did she make you get vasectomy?” while looking quite concerned:

Jay Cutler, cool as a cucumber and not at all growing defensive, replies, “I don’t think you can make anyone get a—I don’t even think that’s legal.” The scene then immediately cuts to Kristin mid-interview saying, “Yeah, I made him get a vasectomy.”

So there you have it. I just hope Kristin doesn’t change her mind. You have no idea the physical toll that multiple vasectomies has on a person.

The Most Jay Cutler Moment of the Week

“Boss is outta town, so I’m making sure you guys are staying in line.” So Jay Cutler announces as he strolls into the Uncommon James office while Kristin is in L.A. He really comes in hot:

He basically morphs into Miranda Priestly from The Devil Wears Prada—or maybe more accurately, he morphs into whatever it would’ve looked like if Miranda Priestly’s husband decided to be boss for a day in The Devil Wears Prada. Look at how he’s sitting while criticizing every person in the room:

And then, as quickly as he arrived, he leaves, mumbling “I can’t be a part of this anymore” on his way out. Just to add in a little more background, upon his arrival at Uncommon James, Reagan asked him what his plans were for the day and he replied, “You’re looking at ‘em.” So … what did Jay do after he left the office? He thought a trip to the store was gonna fill his entire day? He was there for probably five minutes! I have to assume he spent the rest of the day Googling “How to do sex good”—that’d at least explain some things.

See you next week, when Kristin travels to Miami and Jay … stays home I assume? I can’t imagine he’s very welcome in Miami.