Jay Cutler is not just any NFL player but one who has been widely and devotedly followed. His marriage to ex-wife Kristin Cavallari was documented on E! Series Very Cavallari. However, the couple separated in 2020. Since then, the Chicago Bears franchise leader has been linked to several names. However, Samantha Robertson became the lucky lady to win his heart.
Jay Cutler and Samantha first made their relationship public when they went Instagram official in September 2023. It came after Robertson posted a carousel of photos while spending time with the NFL player in France.
The photos were of a lavish wedding where Samantha was Cutler’s first wife.
A few days later, Robertson posted another photo with Jay Cutler after they returned home from their international trip. The post’s caption reads, “Sunsets never disappoint in Montana.”
In this Instagram post dated September 25, 2023, the CUTS co-owner asked Samantha when she planned to travel again. Responding to them, Samantha said that she was ready for the moment they left.
Following the revelation of their romantic relationship, an insider told Life & Style that Cutler and Robertson had previously been close friends for years.
“It’s only been a few months, but they’re already pretty serious,” the source said.
Although the Gratis Beer founder doesn’t post much about his love life online, he once shared his affection for Samantha in his Instagram Stories.
On January 19, 2024, Cutler, Kristin Cavallari’s ex-husband, surprised his followers with photos of “J(heart) Sam” drawn in the sand, tagging his lady as well.
Then came November 7, 2024, when fans noticed that Samantha had a ring on her left hand. This was during the Yellowstone premiere.
While many were excited to see the jewelry on Robertson’s hand, believing that Jay Cutler would have popped the question, within a span of two weeks, People reported that the couple was now engaged.
Samantha has two daughters, Sophia and River, with her ex-husband.
Also read: Kristin Cavallari’s Weight Loss: How She Went From 114 Pounds to 102 Pounds
