Kramer, 37, and Cutler, 38, have been on one date, Yahoo Entertainment can confirm. "It's not that random," an insider says, noting they both live in Nashville and have gone through "very public divorces." Cutler and Cavallari announced in April 2020 they were separating, while Kramer filed for divorce from Mike Caussin earlier this year.
A source tells People that Cutler may have had other intentions when choosing his dinner companion.
"Jay was trying to make Kristin jealous by going on this public date with Jana. He's not happy she's dating Chase and has been trying to get Kristin back," claims the insider.
As for how Cavallari feels, she's not bothered Cutler is dating but blocked Kramer because she "doesn't have time for this kind of [drama]," a separate insider tells Yahoo Entertainment. (Reps for Cavallari and Kramer have not commented.)
In April, it was reported Kramer was leaning on friends — like Cavallari — amid Caussin's infidelity. An insider insists to People the two are not close.
"Kristin and Jana are just acquaintances and have only met twice. They're not friends," the source noted. One of Yahoo's sources disputes this and says it is "a little shady."
Cutler recently said "it's hard as hell" dating again.
"Meeting people is hard," he explained on his Uncut With Jay Cutler podcast. "I think finding out what people really want from you, I think that's probably an issue. I'm at a different phase of my life now with kids and priorities have just changed. It isn't just a purely selfish play by my part."
Cavallari, 34, and Cutler are co-parenting their three kids, sons Camden, 9, and Jaxon, 7, plus 5-year-old daughter Saylor. Kramer and Caussin share two kids: Jolie, 5, and Jace, 2.