Kristin Cavallari’s ex-husband, Jay Cutler, has beaten her to the altar, finding true love after their highly publicized split and divorce in 2020. While the former NFL star is gearing up to tie the knot, the reality TV alum continues navigating the dating world. But that doesn’t mean she isn’t keeping busy in the romance department.
On Tuesday, People exclusively confirmed that Cutler is engaged to his girlfriend, Samantha Robertson. Robertson was seen sporting a dazzling sparkler at the Yellowstone Season 5B premiere on Nov. 7, fueling speculation about the couple’s big news. While it remains unclear when exactly Cutler popped the question, his representative did not respond to requests for comment.
Since his split from Cavallari, Cutler has been linked to several women, including Kelly Henderson, Shannon Ford, and Madison LeCroy. However, his only confirmed romance before Robertson was with actress Jana Kramer.
Cutler and Kramer dated briefly in 2021, and many thought they were a great match. However, an insider later revealed to Us Weekly that the former Denver Broncos quarterback pursued the One Tree Hill actress primarily to make Cavallari jealous. Around the same time, Cavallari had started seeing country singer Chase Rice, adding to the complicated dynamics between the exes.
The revelation about Cutler’s intentions caused a strain, and his relationship with Kramer “fizzled out” after just a few months. Following their breakup, Kramer candidly admitted her fear of being deceived again, saying, “I’ve been so fooled that I’m terrified to be fooled again.”
It then took two years before Cutler could move on, and it all started when he met Robertson. Just like the former footballer, who has sired three kids with Cavallari — Camden, 12, Jaxon 10, and Saylor, 8 — Robertson has children from her previous marriage to Trace Ayala, daughters Sophia and River.
Meanwhile, Cavallari wasted no time jumping back into the dating pool after her split from Cutler, according to Us Weekly. She dated comedian Jeff Dye for five months starting in October 2020, though their relationship was reportedly casual from the outset.
In August 2021, the Laguna Beach alum moved on to Chase Rice. However, their romance was short-lived, ending within three months. After Rice, Cavallari seemed to take a break from dating until she was linked to model Mark Estes in February of this year. Despite their 13-year age gap, the pair quickly hit it off. Unfortunately, the relationship ended after seven months.
Now fans are hoping Cavallari will find “the one” for her. Earlier this month, she admitted that she’s still looking, but she now has a major requirement for her next partner. According to her, she wants someone who has had a vasectomy so she does not have to worry anymore about getting pregnant.
Though she’s keeping mum on who she’s seeing nowadays, Cavallari was not shy to admit to her friend Justin Anderson in a TikTok video she shared last Sunday that she has multiple men in rotation. Anderson then let it slip while doing the viral “Suspect Challenge” trend that his friend hooked up with Jason Statham and country singer Morgan Wallen.
Even though finding true love seems elusive for Cavallari, she’s not lacking in attention. For now, it looks like her dating life is filled with plenty of action, even if “forever” remains out of reach.
