Entertainment Music Country Jana Kramer and Jay Cutler Pose Together for First Time During Date Night in Nashville Jana Kramer and Jay Cutler stepped out on Wednesday to attend the private VIP opening of The Twelve Thirty Club rooftop bar in Nashville By Rachel DeSantis Rachel DeSantis Instagram Twitter Rachel DeSantis is a writer/reporter covering music at PEOPLE. She has held various roles since joining the brand in 2019, and was previously a member of the human interest team. As a music writer, Rachel interviews everyone from rock-and-roll legends to up-and-coming stars for magazine feature stories and digital news stories. Rachel is based in New York City, and previously worked as an entertainment reporter at the New York Daily News after getting her start as an Entertainment Weekly intern. She has a bachelor's degree in journalism from the University of Maryland. People Editorial Guidelines Published on September 14, 2021 12:45 PM Share Tweet Pin Email Jana Kramer and Jay Cutler are taking their budding romance public! The country singer, 37, and the retired NFL star, 38, stepped out for the opening of The Twelve Thirty Club rooftop bar in Nashville on Wednesday and snapped a smiling photo together. The next day, the pair traveled to Greenville, South Carolina for Nate Bargatze's comedy show on Thursday night. "Jay and Jana had a lot they bonded over with how their divorces played out," an insider previously told PEOPLE. Kramer filed for divorce from retired NFL player Mike Caussin, 34, in April amid allegations of infidelity, while Cutler and his ex-wife Kristin Cavallari, 34, announced their split in 2020 after 10 years together. The pair previously went on one date before Wednesday night's event, a source told PEOPLE, prompting Cavallari — who is now dating country singer Chase Rice — to block Kramer on social media. Jana Kramer and Jay Cutler with guests. Jason Bihler "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," the source speculated. Another insider, however, insisted that the Whine Down podcast host 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." Jana Kramer and Jay Cutler 'Bonded Over' Their Divorces, Says Source as They Step Out for More Dates Kramer and Caussin share daughter Jolie Rae, 5, and son Jace Joseph, 2, while Cutler and Cavallari are parents to sons Camden Jack, 9, and Jaxon Wyatt, 7, and daughter Saylor James, 5. Meanwhile, Shannon Ford was also in attendance at the Twelve Thirty Club opening alongside Kramer and Cutler. Guest with Shannon Ford. Jason Bihler Ford rose to fame on Cavallari's E! series Very Cavallari, but was fired from her position as social media director of Uncommon James, the Laguna Beach alum's jewelry company, in the show's season 2 premiere. RELATED VIDEO: Jana Kramer Says She's Ready to Love Herself Again as She Shares Breast Implant Results amid Divorce She previously opened up about getting lunch with Cutler, her former boss's ex, in Charleston in November 2020, video of which Cutler shared to Instagram. Kristin Cavallari Is Dating Country Star Chase Rice: 'They're Having Fun Together,' Says Source "People don't realize this, but I was with my mom and my grandma," she said on the Not Skinny But Not Fat podcast, explaining that her family members weren't shown in Cutler's video. "That's how not spicy it was." "I wanted to be, like, the cool girl that was genuinely just like enjoying a drink with her friend and Jay. So I was like, I'm not going to make this weird at all. I want to prove to them that I'm like, not weird," she added.