Former NFL Quarterback Jay Cutler Is Now Engaged Following His Divorce From Kristin Cavallari

Jay Cutler (Photo by Jonathan Daniel/Getty Images)

Former NFL quarterback Jay Cutler has always been in the spotlight, but he was never really comfortable with having his personal life in the media.

Unlike his ex-wife, Cutler likes to go through his trials and tribulations off of social media and let things happen the natural way.

Case in point, Cutler found happiness with Samantha Robertson, who is a mother of two children.

If you check his social media handles, you won’t see many pictures of him and Robertson. This had many wondering whether they were still together.

Fast forward to this week, and Jay Cutler has shockingly announced that he is once again engaged to be married, PEOPLE reported.

Neither Jay Cutler nor Robertson have announced the engagement news. However, she was reportedly spotted rocking a stunning diamond sparkler on her finger when they attended the “Yellowstone” Season 5B premiere together earlier this month.

This news comes mere weeks after he was arrested for a DUI.

Cutler and Robertson went public with their relationship in September 2023, which was three years after he divorced Kristin Cavallari. They were together for 10 years and married for seven when the two got divorced in 2020.

Jay Cutler’s Engagement Comes One Month After His Arrest

Former NFL quarterback Jay Cutler is reportedly engaged to their girlfriend, Samantha Robertson, three years after his divorce from reality television star Kristin Cavallari.

Neither he nor Robertson has spoken about it.

Robertson, a mother of two, was spotted wearing a diamond ring.

This is shocking news as Cutler was not having a great time in October when he was arrested for DUI and gun possession in Tennessee.

Police stated at the time that Jay Cutler smelled strongly of alcohol and was slurring his words, and two handguns were found in his car.

He was booked on one count of driving under the influence, one count of failure to exercise due care to avoid a collision, violation of implied consent law, and possession of a handgun while under the influence.

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