Jay Cutler is not just any NFL player but one who has been widely and dedicatedly followed. His marriage to ex-wife Kristin Cavallari was documented on the E! series Very Cavallari. However, the couple separated in 2020. Since then, the Chicago Bears franchise leader has been linked with many 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 back in September 2023. This happened when Robertson posted a carousel of pictures while spending time with the NFL player in France.
The pictures were from a lavish wedding where Samantha was Cutler’s plus one.
A few days later, Robertson posted one more photo with Jay Cutler as they arrived back home from their international trip. The caption for this post read, “Sunsets in Montana never disappoint.”
In this Instagram post from September 25, 2023, the CUTS co-owner had asked Samantha when she was planning to go on a trip again. Replying to him, Samantha mentioned that she was ready the moment they had left.
Following the revelation of their romantic relationship, an insider stated to 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 added.
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, the former husband of Kristin Cavallari, Cutler amazed his followers with pictures of “Jay [heart] Sam,” drawn in the sand while also tagging his woman.
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, assuming that Jay Cutler might have popped the question, within the period of two weeks, People reported that the couple was now engaged.
Samantha shares two daughters, Sophia and River with her ex-husband.
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