Kristin Cavallari’s ex Jay Cutler reportedly gets engaged to Samantha Robertson 2 years after divorce

LOS ANGELES, CALIFORNIA: Former Chicago Bears quarterback Jay Cutler recently got engaged to his girlfriend Samantha Robertson, as confirmed by multiple sources.

The news comes two years after Cutler finalized his divorce with television star Kristin Cavallari, who has since wished that "he finds someone" and "gets remarried".

Cutler and Robertson are yet to confirm the reports of their engagement themselves. However, the couple was spotted attending the 'Yellowstone' Season 5B premiere on Thursday, November 7, where Robertson wore a dazzling engagement ring on her finger.

When did Jay Cutler and Samantha Robertson start seeing each other?

Jay Cutler and Samantha Robertson went public with their relationship in September 2023, according to Page Six, when the latter shared photographs of a wedding that they attended together in France. 

"Vive la France 🇫🇷Congratulations @chanelhandel @amackenzietemplar. The most beautiful wedding," she wrote in the caption. 

Later in the same month, Robertson posted a picture from their trip to Montana where she is seen cozying up with her partner.

The caption read, "Sunsets in Montana never disappoint."

Since then, the couple managed to keep their relationship mostly under wraps, until the news of their engagement was shared by insiders.

Jay Cutler's previous marriage with Kristin Cavallari

Prior to his relationship with Samantha Robertson, 41-year-old Jay Cutler was married to Kristin Cavallari, with whom he shares three children, sons Camden, 12, and Jaxon, 10, and daughter Saylor, 8.

The couple separated after seven years of marriage in 2020, and their divorce was finalized in 2022. However, Cavallari remains a well-wisher of her ex-husband.

During her appearance on the 'Call Her Daddy' podcast back in 2022, the reality TV star and fashion designer stated, "I hope that he (Cutler) finds someone, I really do. I want him happy. My kids benefit from that, you know. So I hope that he gets remarried."

Reflecting on their divorce, Cavallari said on her 'Let's Be Honest' podcast in October, "My heart broke in my marriage. And even though I'm the one that walked away, it was not what I wanted. It was not what I had envisioned. And I really tried f**king everything I could."

On her side, Robertson had been married to actor Trace Ayala, with whom she shares two daughters, Sophia and River. She often posts their pictures on Instagram.