Kristin Cavallari Reveals She And Jay Cutler Dated Again After Their Divorce

screenshot very cavallari
(Image credit: E!)

This is Very Cavallari of Kristin Cavallari and Jay Cutler. The former Hills star and ex-NFL player had a second wind of prominence with their E! reality series, which ran for three seasons. Fans saw them procure llamas and wisecrack at the other's expense, but their arguments caught on camera seemed to pave the way for their divorce announcement last year. Apparently, though, the former couple were still willing to try some out of the box ideas together – because Cavallari shared that they actually tried dating again not so long ago.

In the interim of their divorce being held up (reportedly due to asset disagreements), the two are said to have been dating around. Kristin Cavallari was, at one point, linked to a Southern Charm star during the show’s involvement in A-Rod’s alleged love affairs. But she’s now supposedly dating country music singer Chase Rice. Meanwhile, her ex has been thought to be dating country music singer Jana Kramer following her own messy divorce to an ex NFL player. But this was all seemingly after the couple had tried saving their own marriage from divorce. While on the Off the Vine with Kaitlyn Bristowe (opens in new tab) podcast, Cavallari revealed:

Jay and I actually went on a couple dates, like, months and months and months ago. But we did. . . . The thing with Jay and I is we aren't getting a divorce because of love lost, which made it really challenging because we were crazy about each other. And so I just decided I didn't want to be in a toxic relationship anymore and I had to break it off. But that's made it hard and made me sit here and question it for a few months. But then going back and dating him a little bit made me reaffirm, like, 'No, I know that I'm doing the right decision.'

The revelation goes some way to explaining those Halloween pics from last year. Along with their three kids, she and Jay Cutler had posed together for the festivities, dressed as a unicorn and prisoner respectively, which had sparked rumors that they were attempting to reconcile. But it was apparently all for naught or just a co-parenting endeavor because only a month later, Cutler was posting on social media about hanging out with Shannon Ford, who was infamously fired by his ex on Season 2 of Very Cavallari.

On the surface, the move may not seem like the best idea for a couple attempting to make headway in their relationship. But their marriage has reportedly seen even bumpier days, with rumors indicating that Jay Cutler’s calleged affairs are what led to the divorce. Rumors of which the two have attempted to squash in the past.

The supposed “curse of reality TV” is that oftentimes a relationship cannot live to survive it because a couple finally sees itself laid bare. Such has been the case for Kanye West and Kim Kardashian, the latter of whom has complained of a “difference of opinions” and joked that she didn’t like ex’s personality while hosting SNL. And it’s so common within the Real Housewives universe that even a whisper of a vow renewal is akin to hearing the proverbial nail in the coffin. Kristin Cavallari and Jay Cutler, despite all their best efforts it would seem, are now in the same company, too.

Lauren Vanderveen
Movies and TV News Writer

Freelance writer. Favs: film history, reality TV, astronomy, French fries.