Kristin Cavallari Spotted Kissing This Comedian During Night Out in Chicago

Kristin Cavallari was seen on what appears to be a date for the first time since splitting from ex-husband Jay Cutler.

By Kaitlin Reilly Oct 11, 2020 9:38 PMTags

Is Kristin Cavallari moving on from her ex-husband Jay Cutler with a new guy? That's what it looks like in a new video from TMZ, in which the Uncommon James founder can be seen kissing a man the news outlet identified as comedian Jeff Dye

Kristin, who shares three children with her retired NFL player ex, was out in Chicago's Fulton Market when cameras captured her getting cozy with Jeff. The Nashville resident has a store in the nearby area.

An eyewitness tells E! News, "I saw Kristin yesterday afternoon. She was very smiley and giggly and walked right past me and my friends. She was with a guy and walked into the Hoxton Hotel and was escorted to the rooftop. They were alone together. She was definitely super flirty and giggly with him as they were walking."

The eyewitness adds that Kristin had on a "huge smile" while hanging out with the comedian. 

Kristin Cavallari & Justin Anderson's BFF Pics

Kristin has not posted anything about Jeff to social media, but did share video and pictures from what appears to be a getaway up north.

Amy Sussman/Getty Images; Matt Winkelmeyer/WireImage

"6 hours and counting," the Very Cavallari star wrote on Instagram on Oct. 10. "Road trippin with the girls." She later shared Instagram story videos of her and her friends enjoying some fall foliage. 

Kristin and Jay announced their divorce in April, shortly after taking a friends and family vacation to the Bahamas. 

"We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of," Kristin's statement on Instagram read. "This is just the situation of two people growing apart."

In August, Kristin sparked rumors when she posed with her high school boyfriend and Laguna Beach co-star Stephen Colletti on Instagram. Alas, a source told E! News at the time the former couple hadn't rekindled their teenage romance.

Kristin's new potential love interest Jeff was a finalist on Last Comic Standing in 2008 and starred on the travel reality show Better Late Than Never from 2016 to 2018. He currently hosts Jeff Dye's Friendship Podcast. Whether he and Kristin's relationship becomes something more than friendship remains to be seen.