The pair stepped out at the VIP Opening of The Supper Club at The Twelve Thirty Club in Nashville, Tennessee, on Wednesday, September 22, arriving for the event together, according to an eyewitness.
“While they sat at dinner with a whole group afterward, he was outside talking to a friend and she came up behind him and wrapped her arms around him,” the insider tells Us Weekly exclusively. “They definitely weren’t hiding that they’re together and they acted like a couple the whole time.”
The eyewitness adds that Cutler, 38, and Kramer, 37, “spent time a lot of time” with Jessie James Decker and Eric Decker at Justin Timberlake and Sam Fox’s restaurant, which opens to the public on September 28.
“When Eric Church performed, Jana wrapped Jay in a hug and they watched together,” the source explains. “They also danced to Zac Brown together and showed PDA throughout the night.”
The former NFL quarterback and the One Tree Hill alum went on their first date in Music City earlier this month. After the pair were spotted together at Twelve Thirty Club rooftop bar in Nashville on September 8, Kramer revealed that her ex-husband Mike Caussin was also in attendance.
“I would say that was really hard to see him there,” the musician said on her “Whine Down” podcast on Monday, September 20. “See him flirt with other girls and I mean, granted, I was there as well doing my thang but it was really hard. You know what was hard? It looked so easy for him. Does that make sense? Where it’s, like, it looked like it didn’t bother him one second and that, like, hurt, you know? Because I was just, like, he’s just untamed and uncaged and he’s happy.”
Kramer and Caussin, who split in April, share daughter Jolie, 5, and son Jace, 2. She accused him of cheating on her (again) in their divorce documents, with the paperwork being finalized in July.
“Unfortunately, there’s some boundaries around things and he has a lot of resentment toward me, and I’m, like, when things happened repeatedly at certain places, it’s very hard for me to trust when you go out and do those things, so I can totally see him being, like, finally I can go out and drink and be at a bar,” Kramer continued on Monday. “And just seeing him with other women. Is that going to be the future [wife], you know, one with my kids? That’s where I go.”
Cutler, meanwhile, split from Kristin Cavallari in April 2020. The duo share three kids — Camden, 9, Jaxon, 7, and Saylor, 5 — and have yet to finalize their divorce. A source previously told Us that the Hills alum wasn’t thrilled with the former football player’s romance with Kramer as she blocked the “Why Ya Wanna” singer, who she’s known since 2009, on social media.
“It’s not a coincidence that Jay decided to go public with Jana right after news broke that Kristin and Chase Rice are dating,” the source said. “She wouldn’t have blocked her if she wasn’t good friends with her.”
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An insider close to Kramer, meanwhile, argued, “Jana and Kristin have only met a few times in person at events for work. They were never friends. They supported each other’s projects here and there. Their kids have never met.”
Reporting by Emily Longeretta