Jay Cutler Latest Celebrity News & Gossip

Jana Kramer, 37, and Jay Cutler, 38, appeared to have a great time in Nashville, TN on Sept. 8! The singer and NFL star were spotted hanging out together at the opening of The Twelve Thirty Club rooftop bar and didn’t hesitate to pose for pics with fellow partiers. In one pic, which can be seen HERE, they can be seen smiling while standing with two women at the event and looked as comfortable as could be.

Jay Cutler, 38, and Jana Kramer, 37, enjoyed another date night together, as E! News reports the former NFL pro and singer attended comedian Nate Bargatze‘s show in Greenville, South Carolina on Sept. 9.

It appears that Jana Kramer and Jay Cutler are moving forward with their relationship despite Kristen Cavallari’s alleged anger over their first date.

Heating up! Jana Kramer and Jay Cutler had a “fun date night” at Nate Bargatze’s comedy show, a source exclusively tells Us Weekly.

Going strong! Kristin Cavallari was spotted enjoying a PDA-packed night out with new beau Chase Rice days after her estranged husband, Jay Cutler, met up with her friend Jana Kramer.

Pals no more! Kristin Cavallari reacted to Jay Cutler and Jana Kramer’s date by blocking her “friend” Kramer on Instagram shortly after reports emerged about her outing with the Very Cavallari star’s estranged husband.

Where are the reality TV cameras when you need them? After Jana Kramer was spotted on a date with Jay Cutler, Us Weekly is looking into the One Tree Hill alum’s past with Kristin Cavallari.

Kristin Cavallari isn't happy with Jana Kramer going on a date with her ex-husband, Jay Cutler.Cutler and Cavallari announced their decision to split after 10 years together in a joint statement last April. Cavallari has since moved on with country singer Chase Rice, but a source tells ET that she's blocked Kramer on Instagram after she went on a date with Cutler because she had previously thought of Kramer as a friend.«Jana and Jay did go out on a date in Nashville,» the source says.

Two different definitions of friendship — and girl code? Jana Kramer was spotted on a date with Kristin Cavallari’s estranged husband, Jay Cutler, and according to a source, the Laguna Beach alum isn’t thrilled.

Jay Cutler, 38, is evidently romancing Jana Kramer, 37, following his widely-publicized split from Kristin Cavallari, 34, last year. Jay and Jana, who finalized her divorce from her husband of six years, Mike Caussin, in July 2021, recently went on a date in Nashville, and it’s left a sour taste in Kristin’s mouth.

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Kristin Cavallari has a new man.

Jay Cutler's post-divorce love life isn't a walk in the park. On Wednesday, the 38-year-old athlete opened up about getting back in the dating game following his 2020 split from ex Kristin Cavallari and how it comes with a new set of challenges.“It’s hard as hell, really,” Cutler explained during an episode of his  podcast.

Jay Cutler is getting candid about his dating life.

Maybe next time she’ll think before she tweets…

Britney Spears is on the verge of being free of her father, Jamie Spears, as he's agreed to step down as her conservator.The decision is a huge development for Britney and her quest to end the conservatorship.TMZ obtained court documents being filed by Jamie's lawyer.

Kristin Cavallari is wishing her ex-husband Jay Cutler a Happy Father’s Day!

Family forever! Kristin Cavallari posted a Father’s Day tribute for her estranged husband, Jay Cutler, on Sunday, June 20.

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A cable guy has dropped his lawsuit against reality star Kristin Cavallari and her estranged husband, former NFL quarterback Jay Cutler, after one of their dogs allegedly bit him. Cable technician Nathan Beam’s suit was formally dismissed last week against the former couple, who split in April 2020 after seven years of marriage, news station WKRN reported.

Clearing her name. Southern Charm‘s Madison LeCroy responded to “gold digger” claims after her Alex Rodriguez and Jay Cutler drama.

Staying honest! While discussing her past connections to Alex Rodriguez and Jay Cutler, Madison LeCroy made it clear that she has a type and it has nothing to do with being rich.

Kristin Cavallari has her schedule down pat. In May 2020, the reality star, 34, reached a custody agreement for her children with estranged husband Jay Cutler.The pair share three little ones: Camden, 8, Jaxon, 7, and Saylor, 5.

Kristin Cavallari is opening up about her split from Jay Cutler.

One year after her split from husband Jay Cutler, Kristin Cavallari is still figuring out life as a single mother.

Making it work. Kristin Cavallari is finding the silver lining when it comes to coparenting with her estranged husband, Jay Cutler.

Kristen Cavallari's sole focus is her kids when they're in her care. The 34-year-old star has split custody of Camden, eight, Jaxon, seven, and Saylor, five, with estranged husband Jay Cutler - who she split from last year after seven years of marriage - so uses the weeks the trio are with their dad to throw herself into her work and friendships so that she doesn't need to think about anything else when they're with her.

Circumstances for Kristin Cavallari and Jay Cutler‘s divorce are getting more strained. The former football player, 38, is reportedly going after half of ownership of Kristin’s Uncommon James brand, since it was launched while Jay and the Very Cavallari star, 34, were married at the time, per People. A source close to the former couple explained EXCLUSIVELY to HollywoodLife that “the hold up with the divorce has been Jay asking for the money from Uncommon James.”

Kristin Cavallari and Jay Cutler are suddenly stalled out in the middle of their divorce proceedings, and it all comes down to what the former NFL quarterback apparently wants regarding Kristin’s hard work on her business projects!

Kristin Cavallari and Jay Cutler’s divorce has just taken a turn.