Former Chicago Bears QB Jay Cutler Debuts New Romance on Instagram

Former Chicago Bears QB Jay Cutler has apparently moved on romantically, three years after his divorce from fashion designer and author Kristin Cavallari. And his new girlfriend may look familiar to some.

Based on an Instagram post, it appears Cutler is dating designer Samantha Robertson. The latter posted a picture to her account showing the two holding each other close under a radiant sky. “Sunsets in Montana never disappoint,” reads the caption.

Cutler showed up in Robertson comments to ask: “When are we going back?”

"I was ready the second we left," she replied.

Last month, Robertson posted several snaps of the couple in France. That stoked speculation of a relationship between the two, which the newest post seems to confirm.

Cutler has previously said on his podcast Uncut with Jay Cutler that dating after his divorce was “hard as hell” and that "meeting people is hard." Cavallari, too, struggled with the decision and admitted the two even dated after their split. “We aren’t getting our divorce because of love lost," she said on the Off the Vine podcast. “I just decided I didn’t want to be in a toxic relationship anymore.”

The couple married in 2013, and share two sons and a daughter. They announced their divorce in April 2020, which was attributed simply to “growing apart.” The divorce was finalized in June of last year.

Robertson may look familiar to some eagle-eyed celebrity fans. She was previously married to Trace Ayala, who’s best known as a close friend of Justin Timberlake.