Jay Cutler Dated Jana Kramer Just to Annoy Kristin Cavallari, Sources Claim

Jay Cutler and Jana Kramer didn’t find true love in their brief relationship, with an insider spilling to E! News Wednesday that the former football player “broke it off” with the country singer after just a few dates. Cutler, who split from Laguna Beach star Kristin Cavallari in 2020 after nearly seven years of marriage and three children together, was first spotted with the One Tree Hill alum in Nashville last month before they traveled together to South Carolina.

The insider source claimed Cutler only went out with Kramer, recently separated from her husband Mike Caussin, “to get under Kristin’s skin,” but his plan didn’t exactly spark the reaction he wanted. “It didn’t work, so he broke it off. They went out all over Nashville and Kristin didn’t care. That’s it,” the source said. An insider close to Cavallari previously confirmed her feelings on the pairing, saying the Very Cavallari star “does not care and is not bothered,” but did block Kramer on social media, as she “doesn’t have room for this in her life.” Cavallari previously dated comedian Jeff Dye and is now linked romantically with country singer Chase Rice.

Last month, a different source painted Cutler and Kramer’s relationship in a different light, telling E! News they were “bonding” over both ending a high-profile relationship recently and “moving forward one day at a time.” The insider claimed Cutler “isn’t trying to make anyone jealous: He knows his ex has moved on and so has he.”

The former NFL player admitted on his Uncut With Jay Cutler podcast recently that he’s been struggling with being single, calling it “hard as hell” to get back on the dating scene. “Meeting people is hard. I think finding out what people really want from you, I think that’s probably an issue,” he explained. “I’m at a different phase of my life now with kids. Priorities have changed. It isn’t just a purely selfish play by my part.”

Returning to the dating landscape now that social media and dating apps have taken over has been a bit of a shock. “It’s a whole different ball game,” he explained. “You’re not just walking into a restaurant or bar and talking to somebody. That doesn’t exist anymore.”