Jay Cutler and Jana Kramer Dating: See Their Relationship Timeline

Jay Cutler is seeing someone new. Not even a year after he was rumored to be dating Southern Charm‘s Madison LeCroy, Jay’s now attached to actress and country music singer Jana Kramer. The duo have been spotted together a couple times, and things seem to be heating up as sources told US Weekly they “acted like a couple” during their night out at the VIP opening of The Supper Club at The Twelve Thirty Club on September 22 in Nashville, Tennessee. Not to mention, there are some surprising connections to Music City, and yes, even Kristin Cavallari. Keep reading below for more about Jay and Jana’s relationship timeline, as well as all those shared connections.

Jay Cutler & Jana Kramer: a timeline of their romance

Jay Cutler and Jana Kramer first made headlines with a possible romance earlier this month when the duo were seen out in Nashville. Cutler and Kramer ventured out in Nashville again recently with the club opening, apparently hanging out with fellow Tennesseans Eric and Jessie James Decker, who were also in attendance.

Jana revealed on her Whine Down podcast that it was “really hard” to see her ex-husband Mike Caussin while out on September 8, even though she was “there as well doing [her] thing.” She and Mike finalized their divorce in July of this year; they share kids Jolie and Jace together. Recently, she opened up about her difficult year through the release of her new single “Voices.” She wrote on Instagram that she “felt strong” and told fans that “you are worth it, you are enough, you aren’t broken.”