"So far it's just been one date," an insider told PEOPLE, stressing that Kramer, 37, and Cavallari, 34, aren't close. "Kristin and Jana are just acquaintances and have only met twice. They're not friends."
Despite this, another source said Kramer turned to Cavallari when she was going through her divorce from Caussin.
As for Cavallari, insiders told PEOPLE and E! News that Cavallari blocked Kramer on social media. "She does not care and is not bothered, but she has blocked Jana over it," a source said to E! News, "She doesn't have room for this in her life."
None of the three have spoken publicly about the reported date.
Romance rumors between Kramer and Cutler began swirling after the Instagram account @cocktailsandgossip posted anonymous tips from people claiming they saw the two together at the Nashville restaurant Bourbon Steak as well as the bar L.A. Jackson.
Kramer filed for divorce from Caussin, 34, back in April following more than a couple of cheating scandals he admitted to, along with his sex addict diagnosis. The former couple -- who share daughter Jolie 5, and Jace, 2, -- finalized their divorce in June.
Following her split from Caussin, the "One Tree Hill" alum was rumored to have moved on with "The Bachelorette" alum Graham Bunn in June. She went on to describe the possible romance as an "entanglement" during an appearance on E! News' "Daily Pop," but later clarified her comments on an episode of her "Whine Down" podcast in June.
"To set the record straight, we are friends and I've known of him for seven years," Kramer said, admitting that she had "no idea" what the term "entanglement" meant. "He was a country radio DJ. I didn't watch his season of 'The Bachelorette,' I didn't even know he was on it."
The country singer said Bunn "reached out" to her following her breakup from Caussin and shared that he understands that she needs "to be alone" at the moment. "I need to go through what I’m going through and I need to do that alone," she explained.
However, earlier this month, Kramer explained to PEOPLE that she's "starting to dip [her] toes" into dating again.
"I think I had to just take some time to be alone, but I'm starting to dip my toes in again. There's still a lot of work I have to do healing-wise, but I am entertaining things," Kramer said. "There have been a few DM slides ... the game's different for me now. I'm not looking to just have a fling. I want to find my person."
Following the divorce, Cavallari briefly dated comedian Jeff Dye. The pair split last spring.
Last month, it was reported that the Uncommon James founder was dating Chase Rice, per PEOPLE. A source told the publication that Cavallari and Rice have "been seeing each other a little over a month," adding that "they were introduced through a mutual friend. ... They're having fun together."