It feels like forever since we all watched the slow-motion car crash that was Jay Cutler and Kristin Cavallari’s divorce. For a while there, it seemed like Jay was perfectly content just being a retired guy on a farm, hanging out with his goats and occasionally popping up in some weird dating rumor that never really went anywhere.
But things changed. Fast.
If you’ve been scrolling through social media lately, you’ve probably seen a new face next to the former Bears QB. Her name is Samantha Robertson, and honestly, she’s not just some rebound. This is the woman who actually got Jay Cutler to put a ring on it.
Who is Samantha Robertson anyway?
Samantha Robertson isn't exactly a household name, but she’s been around the "celebrity-adjacent" world for quite some time. She’s Australian, which explains the accent you might catch in her rare video clips, and she’s a mom of two daughters, Sophia and River.
Before Jay, she was married to Trace Ayala. If that name sounds familiar, it’s because Trace is basically Justin Timberlake’s lifelong best friend and business partner (they started William Rast together). So, she’s used to the spotlight—or at least being near it.
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She and Jay didn’t just wake up engaged, though. They went "Instagram official" back in September 2023. They were in Montana, there was a sunset, and it looked like every other influencer's dream post. But it was the real deal. People close to them say they actually met through mutual friends in Nashville, which makes sense because everyone in that town knows everyone.
The Montana engagement and that ring
The rumors started swirling hard in late 2024. Samantha was spotted at the Yellowstone season 5B premiere in November, and she wasn't just there for the show. She was sporting a massive diamond that could probably be seen from space.
Multiple sources, including People and TMZ, confirmed the news shortly after. Jay Cutler, the man famous for his "don't care" attitude on the football field, had officially proposed.
It’s kinda funny when you think about it. For years, Kristin Cavallari has been saying on podcasts like Call Her Daddy that she actually wanted Jay to get remarried. She said it would be better for their kids—Camden, Jaxon, and Saylor—if their dad was happy and settled. Looks like she finally got her wish.
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Why this relationship feels different
Most of Jay’s post-divorce flings were... well, messy. Remember the whole Madison LeCroy drama? That was a wild few weeks of "receipts" and leaked texts that made everyone look a little bit silly.
But with Samantha, it’s been quieter. More mature.
- Shared lifestyles: Both are parents navigating the world of co-parenting.
- The Nashville connection: They live in the same world, move in the same circles, and don't seem to be chasing the Hollywood vibe.
- Aesthetic harmony: Honestly, if you look at their photos, they just fit. They spend a lot of time outdoors, traveling to places like France and Montana.
Dealing with the "Smokin' Jay" baggage
Being Jay Cutler's girlfriend—and now fiancée—can't be the easiest gig in the world. He’s got a reputation. The internet loves the "Smokin' Jay" memes and the idea that he’s perpetually unbothered by everything.
Then there’s the legal stuff. In October 2024, Jay was arrested in Franklin, Tennessee, for a DUI and illegal possession of a weapon. It was a messy situation where he allegedly rear-ended someone. Samantha has stayed pretty quiet through the legal fallout, which is probably the smartest move she could make.
When you’re dating a public figure with a polarizing history, the best strategy is usually to stay out of the headlines yourself. She’s managed to keep the focus on their family life and their travels rather than the drama.
What’s next for the couple?
We haven't seen a wedding date set in stone yet, but the engagement is very much "on." Given their history, it’ll likely be a private affair—maybe back in Montana or a destination wedding in France, since they seem to love it there.
There's been plenty of chatter on Reddit and Nashville gossip boards about how they met or whether there was overlap with previous relationships, but at this point, they’re moving forward as a blended family. Samantha’s two girls and Jay’s three kids are the real priority here.
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If you're following the story, keep an eye on:
- Wedding announcements: They’ll likely drop a random photo after the fact rather than a big "Save the Date" to the media.
- Co-parenting dynamics: How Kristin and Samantha get along will be the real test of whether this "happy ending" stays happy.
- Jay's legal updates: The DUI case in Tennessee is still a factor that could complicate their timeline.
The biggest takeaway here is that Jay Cutler seems to have finally found his match in Samantha Robertson. She’s someone who understands the pressure of high-profile relationships but seems perfectly happy living a quieter life behind the gates in Tennessee.
If you want to stay updated on their latest moves, your best bet is following Samantha's Instagram—she’s much more active than Jay is, and she’s usually the one giving the world a glimpse into their life together.