Kristin Cavallari knows what it’s like to lose a friend.
The Very Cavallari star reflected on the demise of her relationship with former pal Kelly Henderson in 2020, revealing how Kelly’s interactions with her then-husband Jay Cutler created friction in their friendship.
“I’ve really had one adult friendship with a woman that blew up in my face,” Kristin—who opted not to mention Kelly by name as she described the details of their fallout—said on the Nov. 19 episode of her Let’s Be Honest podcast. “I felt as though one of my best friends at the time—who was on the Very Cavallari show—I don’t think she ever had an affair with my ex-husband. But the viewers of the show, season two, were accusing them of having an affair.”
Kristin explained that she felt the unnamed friend was “capitalizing” on the speculation by “the way she would speak about [Jay] on social media” and “trying to add fuel to the fire,” prompting the Laguna Beach alum to send her then-BFF an email addressing the matter.
“I in no way, shape or form attacked or blamed,” she insisted. “It was just, ‘This is how I feel.’ And it blew up in my face.”
While the women’s relationship ultimately never recovered, Kristin said she learned a valuable lesson from the ordeal.
“You have to just move on from it, unfortunately,” she concluded, “and be thankful for the time that you had together.”
Kristin—who shares kids Camden, 12, Jaxon, 10, and Saylor, 8, with Jay—previously discussed the friendship fallout on her E! reality series.
“When season two was airing, there was a lot of talk on social media about Jay and Kelly having an affair,” Kristin said during the show’s season three premiere in January 2020. “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.”
That May, a source told E! News the root of the matter was “100 percent not Jay” and was instead “Kelly seeking attention.” For her part, the hair and makeup artist denied ever being romantically involved with the retired NFL star.
“I'm just gonna go ahead and put this out there,” Kelly said during a May 2020 appearance on the All's Fair podcast. “There was never an affair, I have nothing to do with their divorce and I am not dating Jay Cutler.”
Kristin announced plans to divorce Jay in April 2020, writing on Instagram at the time, “This is just the situation of two people growing apart.”
E! News has reached out to Kelly and Jay for comment but hasn’t heard back.
For a look back at Kristin and Jay’s relationship, keep reading.
Honeymoon Stage
K.Cav and the then-Chicago Bears quarterback first spark romance rumors in 2010 after they meet for the first time following his football game. "They really hit it off," a source tells E! News at the time. "He's crazy about her and she thinks he's cute."
Love at First Sight
Of the early days of their romance, The Hills star writes in her book, Balancing in Heels, "We hung out two nights later, and that began a swift and intense romance. I flew back to Chicago at least every two weeks. When we were apart, we texted constantly, and he wrote me the sweetest love emails. He was the strong, manly man I wanted but had a sweet, romantic side as well."
Put a Ring On It
After just eight months together, Cutler pops the question. But not long after, Cavallari calls off the engagement and the exes even return their wedding gifts.
"At that moment, something wasn't right," she writes in her 2016 book. "A few things needed to change, and I knew the only way Jay would see how serious I was, was if I ended the relationship."
Back Together
Then in the fall of 2011, Kristin and Jay are back together—and engaged!
"It was so silly," the bride-to-be tells E! News of their reconciliation. "I was in the airport, leaving Chicago. We had just spent however many days together and we were texting and somehow it came up, like, 'Oh, shall we get married?' We're like, 'Yeah, OK.' And then he sent my ring in the mail. So I actually had my ring sitting at home for a couple of weeks before I put it on."
Hey Mama!
In Aug. 2012, Kristin and Jay welcome their first child together, a baby boy named Camden Jack.
Wedding Bells
They do! Kristin and Jay officially tie the knot in front of their nearest and dearest in Nashville in June 2013.
Baby No. 2
It's a boy! In May 2014, Kristin gives birth to Jaxon Wyatt. She tells E! News of her pregnancy experience, "I'm lucky. Both pregnancies have been really easy for me, I've just been really tired. It's just one of those things where I could literally sleep all day everyday but I'm snapping out of it a little bit now that I'm in the second trimester."
Mama's Girl
More than a year later in Nov. 2015, the proud parents welcome daughter Saylor James.
"Kristin and Jay are so happy!" an insider dishes. "They were surrounded by friends and family. Kristin is so thrilled to welcome her new baby girl to her family. Jaxon and Camden are excited to be older brothers. She is feeling great!"
Sharing Her Truth
Kristen speaks candidly about her and Jay's marital struggles, and says therapy "100 percent" saved their relationship.
"Jay and I, our relationship, we are very honest. We don't have a perfect relationship," she tells SiriusXM's Wake Up With Taylor. "We work on it. We're in therapy."
Losing Her Brother
Kristin's brother, Michael Cavallari, is found dead in 2015. As she approaches the one-year anniversary of his passing, the Uncommon James CEO tells E! News exclusively that Jay has been her saving grace throughout the ordeal.
"It's been tough, it's been a roller coaster...I'd be lying if I said it wasn't hard," she says, "I'm going to be with my family on the actual day, which hopefully will help. Talking about it is probably the most important thing so I'm lucky I have a great support system with my immediate family, with Jay and with my parents as well."
Pulling Back the Curtain
Kristin and Jay welcome cameras into their Nashville home on E!'s Very Cavallari. The reality TV series chronicles their ups and downs and no topic in their marriage is off limits.
Cheating Rumors
Kristin experiences a major fallout with her best friend, Kelly Henderson, who is accused of having an affair with Jay.
"When season two was airing, there was a lot of talk on social media about Jay and Kelly having an affair. Not for one second have I ever thought that it was true," she recalls on Very Cavallari. "It wasn't the actual accusations of them having an affair that made me upset, it was how Kelly went about it."
One Last Hurrah
Kristin and Jay take their final vacation together as a couple with their kids. Judging by their Instagram posts, nothing seems amiss during the Bahamas getaway.
Going Their Separate Ways
On April 26, 2020, the celebs take to Instagram to announce their decision to divorce.
"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," Kristin writes in part.
Mini Reunion
The former couple shares the same message on Instagram, writing, "The world is full of users. 10 years. Can't break that." However, a source exclusively tells E! News nothing has changed between them. "They are friends and they are single. They will always have each other's back," the insider explains.