Jana Kramer and Jay Cutler 'Bonded Over' Their Divorces, Says Source as They Step Out for More Dates

The country singer — who finalized her divorce from ex Mike Caussin earlier this year — is spending time with Kristin Cavallari's ex, multiple sources previously told PEOPLE

Jana Kramer, Jay Cutler
Jana Kramer and Jay Cutler. Photo: Frazer Harrison/Getty; Todd Williamson/Getty

Jana Kramer and Jay Cutler are heating up.

The country singer, 37, and former NFL quarterback, 38, went out on another date Wednesday night in Nashville, an insider tells PEOPLE, and then traveled to Greenville, South Carolina for Nate Bargatze's comedy show on Thursday evening.

"Jay and Jana had a lot they bonded over with how their divorces played out," says the insider.

The Whine Down podcast host filed for divorce from retired NFL player Mike Caussin, 34, in April amid allegations of infidelity while Cutler and his ex-wife, Kristin Cavallari, announced their split in 2020 after 10 years together.

A source previously told PEOPLE Cavallari blocked Kramer on social media after finding out about her date with Cutler, adding that the Uncommon James founder — who's now dating country singer Chase Rice — felt betrayed by the One Tree Hill alum.

RELATED VIDEO: How Jana Kramer Taps into Her Strength During 'Hard Days': 'It's Okay to Feel All the Feels'

"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," speculated the source.

However, the insider insists Kramer and Cavallari were "never close friends" and that there is "no point in Jay trying to make Kristin jealous as she has moved on and so has he."

On the same day PEOPLE broke the news that Kramer and Cutler are spending time together, Cavallari was spotted "making out" with her new flame, country singer Chase Rice, at Losers Bar and Grill in Nashville.

PEOPLE previously confirmed Cavallari, 34, has been dating Rice, 35, since earlier this summer.

"It's still early days and they're not exclusively dating, but they're having a good time and enjoying getting to know each other," said a source.

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