Did Jay Cutler Cheat On Kristin Cavallari? How Scandal Ended Her Relationship With BFF Kelly Henderson

Cavallari has dumped her best friend.

Did Jay Cutler Cheat On Kristin Cavallari? How Scandal Ended Her Relationship With BFF Kelly Henderson Getty

When the new season of Very Cavallari premiered in January 2020, one former cast member was conspicuously missing. Kelly Henderson was off the show and apparently out of Kristin Cavallari's life as well.

In the opening episode, Cavallari explained to viewers (and her friends) that there were troubling rumors about an affair between Henderson and Cavallari's husband of seven years, ex-NFL player Jay Cutler. Cavallari got really upset when Henderson didn't handle the rumors the way Cavallari would have liked.


And with Cavallari's recent shocking announcement that she'll be divorcing Cutler, fans have naturally wondered whether or not the cheating rumors had anything to do with it. 

RELATED: Why Are Kristin Cavallari And Jay Cutler Getting Divorced? The Hints Their Marriage Was In Trouble


Now the BFFs are BF-Nevers, and Cavallari and Cutler are ending their marriage.

Did Jay Cutler cheat on Kristin Cavallari with Kelly Henderson? Let's get straight to it. Here's what we know about the cheating rumors and Cavallari's divorce announcement. 

Henderson has been Cavallari's friend and castmate for years. 

Very Cavallari premiered on E! in 2018 and featured the life of reality star Kristin Cavallari, her former NFL quarterback husband, Jay Cutler, and their three kids (who aren't featured on camera.) The former Laguna Beach and Hills star is now a business owner of jewelry line Uncommon James and her new series focuses a lot on growing her brand as well as her home life in Nashville, a life that Henderson was a big part of.


Henderson is a Nashville based makeup artist and "glam specialist" (who knew that was an official specialty?) and she works with celebrity clients like Dierks Bentley, Jason Aldean, Luke Bryan, Sam Hunt, Kip Moore, Kelsea Ballerini, Aubrie Sellers, Tucker Beathard, and Sam Palladio to name a few.

Naturally, she also has a lifestyle website and an active Instagram account where she posts photos of her work, promotes her podcast, and generally does the influencer thing. She gets a boost from being on TV with her best friend as well. 



A post shared by Kristin Cavallari (@kristincavallari) on Nov 11, 2018 at 11:00am PST


Cavallari with Henderson and fellow Cavallari BFF Stephanie Biegel.

Did Jay Cutler cheat on Kristin Cavallari with Kelly Henderson? Cavallari dropped a bombshell in the premiere of the new season.

In a face-to-face with cameras on the premiere episode of the recent season, Cavallari sadly told her fans that her biggest change had been a personal one. “The biggest change in my personal life is that my best friend Kelly and I haven’t talked in two months,” Cavallari revealed. “We’ve had a major falling out and it’s just been breaking my heart.”

“When season 2 was airing, there was a lot of talk on social media about Jay and Kelly having an affair,” she continued. “Not for one second have I ever thought that it was true. It wasn’t the actual accusations of them having an affair that made me upset, it was how Kelly went about it.”


What were the rumors about Cutler and Henderson?

There was an episode in the second season where Henderson and Cutler met up for drinks and to talk about Henderson wanting to find love. The meet-up was to set the stage for an upcoming storyline about Cutler picking potential dates for Henderson, but the vibe in the room was a little intense and viewers couldn't help but notice.

One Twitter user commented at the time:

Another user a few months later noted their recent falling out and said, "Did Kristen finally let go kelly because she finally realizes and notice kelly was hitting on jay?" One other fan of the show questioned, "#VeryCavallari maybe Jay and Kelly have a thing, maybe that's why Kelly can't find the 'right' man."


RELATED: Who Is Kelly Henderson? Everything To Know About Kristin Cavallari's Ex-BFF —​ And Whether She Cheated With Jay Cutler

So what did Henderson do wrong?

Cavallari stated that while she didn't believe the affair rumors, she was hurt by how lightly Henderson took the situation and wished her friend threw cold water on it. Instead, she felt Henderson used the rumors to boost her own online presence. 

“[Henderson] was accused of having an affair with Jay last season of the show, which, fine, I get it — that’s a lot for her to deal with, too,” Cavallari vented to her friends Justin Anderson and Stephanie Biegel on the show.


“But she wanted to post something about it. I was like, ‘Don’t post anything about it! That’s the last thing you do,’” she continued. “Why do you want to post about that? To get more attention about it. If I was accused of having an affair with your husband, I wouldn’t say his f—ing name on social media. Like, like come on! It kind of blows my mind.”

Cavallari tried to reach out to Henderson about it to talk it out.

Cavallari revealed that she sent Henderson an email explaining her feelings about the whole situation, which prompted a defensive response from Henderson. Cavallari said she didn't want to lose the friendship forever, so instead of making any final decision, she took her husband's advice and took some time to herself.

So was there an affair or not?


It doesn't seem like there was actually anything going on between Henderson and Cutler. Although this being reality TV, the affair could have happened and this storyline is what Cutler and Cavallari agreed to do to save their marriage. 

More likely, however, is that Cavallari was legitimately annoyed by the rumors and how Henderson handled them and E! ran with that conflict to anchor the new season of the show. Both Henderson and Cutler also later denied the rumors.

Cavallari opened up to Heidi Montag and Audrina Patridge about the falling out.

On an episode this season, the reality star met up with her old pals and fellow The Hills alums, Heidi Montag and Audrina Patridge. During their night out, Cavallari opened up to her friends about the drama surrounding her former BFF, Henderson.


After Patridge commented how bad she felt about the falling out, Cavallari responded, "It's just weird because I've only ever known Nashville with Kelly. I've known her for seven years. It's a long time and she was my best friend."

She also told her friends that Henderson had told her other friend, Justin Anderson, that she was only "doing the show as a favor." Cavallari also revealed that nothing about Henderson's behavior "really added up." 

Patridge went on to say, "Cameras and a little bit of fame, it brings people's true colors out." And then compared the situation to Montag's falling out with Lauren Conrad. Montag sympathetically agreed, commenting, "It's hard when you lose your best friend. That is such a deep blow."

The following day after the meetup, Patridge told Cavallari that a man had come up to her that night and commented on the feud, "This guy came up to me, he was like, 'We have someone in common. My best friend is Kelly and Kristin is a b****.'"


Patridge then defended her friend, saying, "So I was like, 'You know, if you think Kristin's a b****, at least she's black or white. There's no grey, Kristin's very straightforward. You know exactly where she stands and that's respectable.'"

Cavallari was, of course, grateful for the support. 

Cavallari has announced that she and Cutler are divorcing.



A post shared by Kristin Cavallari (@kristincavallari) on Apr 26, 2020 at 10:11am PDT

The reality star shocked her fans this past weekend when she took to Instagram to announce her separation from Cutler.

She wrote, “With great sadness, after 10 years together we have come to a loving conclusion to get a divorce. We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of. This is just the situation of two people growing apart. We ask everyone to respect our privacy as we navigate this difficult time within our family.”

The couple married back in 2013 and share three kids. However, sources claim that cheating had nothing to do with the couple's split and that they had actually been experiencing marital issues for awhile: "This isn't out of the blue. They've been trying to make it work for a while."


Cavallari herself had also recently opened up about her marriage, saying, "Jay has been great, yes. From the outside, things are so perfect and things are so great. But actually, they're not. And that sucks. It sucks. That's the thing, though, with marriage... it's ups and downs. 

But in two months we could be up here again... that's how we've always been, our whole relationship. It is what it is. Jay and I have problems. I've always been very vocal about that. We have to work at our relationship, so hearing him say that we're perfect is kind of silly to me. We definitely have issues."

RELATED: 7 Awkward Things About Kristin Cavallari and Jay Cutler's Relationship, Including Their New Reality Show Very Cavallari

Rebekah Kuschmider has been writing about celebrities, pop culture, entertainment, and politics since 2010. She is the creator of the blog FeminXer and she is a cohost of the weekly podcast The More Perfect Union.


Editor's Note: This article was originally posted on January 14, 2020 and was updated with the latest information.