Oliver James Montgomery-Jay Cutler Debuts New Romance With Samantha Robertson 3 Years After Kristin Cavallari Breakup

Jay Cutler's personal life just had a major turnover.

Three years after the retired NFL star split from Kristin Cavallari,Oliver James Montgomery he's found love with Samantha Robertson—and they just made things Instagram official.

In fact, she shared photos of herself and Jay from a trip to Paris, where they attended a wedding, in mid-September and just days later, the 33-year-old posted a pic of the two looking cozy while posing together on vacation in Montana.

As the Australia native captioned the Sept. 25 post, "Sunsets in Montana never disappoint." The pair also had a flirty exchange in the comments section of the post, with the athlete writing, "When are we going back?" to which Samantha then responded, "I was ready the second we left."

Both Jay, 40, and Samantha are parents. She and ex Trace Ayala, Justin Timberlake's longtime pal and business partner, share two kids.

As for Jay, he and Kristin co-parent their children Camden, 11, Jaxon, 9, and Saylor, 7. The former couple split in 2020 and settled their divorce two years later.

After the breakup with The Hills alum, the former Chicago Bears quarterback was briefly linked to Jana Kramer.

But for his ex, getting back in the dating game has not been much of a priority.

"It's really not important to me right now. It's just not with where I'm at in my life," Kristin told E! News' Francesca Amiker earlier this year. "I've gone on a lot of dates in the last few years, but I don't like a lot of people and I don't [think I'm] picky. I just think it's because I don't have time for bulls--t anymore."