After the pair were first linked in September 2021, a source told Us Weekly the following month that the twosome had gone “on a few dates.”
Their first outing took place in Nashville, Tennessee. The duo were photographed at the opening of the Twelve Thirty Club rooftop bar in the Southern City, getting cozy at the VIP event with pals Jessie James and Eric Decker.
“While they sat at dinner with a whole group afterward, [Jay] was outside talking to a friend and she came up behind him and wrapped her arms around him,” an insider told Us in October 2021. “They definitely weren’t hiding that they’re together and they acted like a couple the whole time.”
“Jay was trying to make Kristin jealous, but Kristin has told friends it isn’t going to work,” an insider close to the Hills alum told Us at the time. “It’s not a coincidence that Jay decided to go public with Jana right after news broke that Kristin and Chase Rice are dating.”
Cutler and Cavallari announced their split in April 2020 after nearly seven years of marriage. They are parents of sons Camden and Jaxon and daughter Saylor.
Kramer, for her part, confirmed her breakup from Mike Caussin — with whom she shares daughter Jolie, and son Jace — in April. They finalized their divorce in July.
Though the One Tree Hill alum and the former Chicago Bears quarterback seemed to be getting along well, a source shared with Us that their romance “fizzle[d] out” quickly. “They’re not seeing each other anymore,” the insider revealed in October 2021.
Two months later, Kramer opened up about her experience dating the ex-NFL player. “I get scared to want to talk about my dating life because I’ve been so fooled that I’m terrified to be fooled again,” the “I Got the Boy” singer revealed during her “Whine Down” podcast in December 2021. “Obviously the whole Jay stuff, that became public because we went out and he was a very public person so obviously that came out, but I never spoke on it because I didn’t know what it was.”
Almost a year after they were first spotted together, Kramer again discussed her relationship with Cutler in an episode of her podcast — though she didn’t name names.
“When this person and I were hanging out, I named his beer company [Gratis] … I named it. I have proof,” the 90210 actress began before seemingly bringing up Cavallari. “Now, this person also got very angry that he named someone else’s business and wasn’t getting compensated. It’s not uncommon to be upset about that.”
Kramer then put more emphasis on “uncommon,” ostensibly referring to the Laguna Beach alum’s company Uncommon James, which she launched during her marriage to Cutler.
“I even gave the whole, like, what it stands for, how you should promote it,” the “Whiskey” singer continued. “And then he would send me, ‘What is this design?’ I was like, ‘This design looks great.’ So then I get a call from Decker — Jessie James because I still told her. And she goes, ‘Oh, it’s out.’ And I go, ‘He did not use the name?’ Oh, and the same design! And my promo for it!”
The country singer added that she wasn’t “asking for a check” from the Indiana native, but wishes she heard from him.
“He could have at least emailed. Here’s my beef, email and say, ‘You know what? Thank you for the name. We’re going forward with it. And I appreciate it,’” she said. “That’s all I wanted … ‘Greetings, branding genius.’”
Scroll down to relive the highlights of Kramer and Cutler’s short-lived romance: