Jay Cutler and Samantha Robertson ​Are Engaged: Inside the Couple’s Romance

Jay Cutler and Samantha Robertson were “close friends” for years earlier they announced their narration successful September 2023. That said, nan brace reportedly were seeing each different while she was married.

When Did Jay Cutler and Samantha Robertson Start Dating?

The erstwhile NFL prima and Samantha became Instagram charismatic successful September 2023.

“Vive la France. Congratulations @chanelhandel @amackenzietemplar. The astir beautiful wedding,” Samantha captioned her September 20, 2023, Instagram post. Jay appeared successful nan first image of nan photograph carousel, wherever he and Samantha were dressed to impressment astatine nan wedding festivities. The erstwhile master jock besides appeared successful different photos successful nan integer collage.

Two days later, Samantha confirmed nan difficult motorboat by sharing a photograph pinch Jay backmost astatine home.
“Sunsets successful Montana ne'er disappoint,” Samantha captioned nan post.

Shortly aft taking their narration public, a root gave Life & Style exclusive specifications wrong nan pair’s romance.

“Jay and Samantha person been adjacent friends for years,” nan root told Life & Style, noting that Jay was pals pinch Samantha’s ex-husband, Trace Ayala, and she was friends pinch his ex-wife, Kristin Cavallari. “Their families hung retired and moreover vacationed together.”

The insider later said that Jay and Samantha were “giving things a shot. It’s only been a fewer months, but they’re already beautiful serious.”

Did Samantha Robertson Cheat connected Her Ex-Husband With Jay Cutler?

After Life & Style shared nan news of Jay and Samantha’s engagement via Instagram connected November 22, 2024, fans flooded nan comments conception pinch cheating rumors.

“You mean nan woman of his bully friend Trace Ayala who busted them having an matter whilst vacationing each together pinch nan kids” 1 instrumentality wrote nether nan post.

In May 2022, In Touch reported that Jay was having a “long-time affair” pinch his champion friend’s wife.

“Jay went connected picnic pinch his kids and his friend and his woman and their kids,” a root told nan outlet astatine nan time. “The hubby and Jay are bully friends and besides neighbors. Their kids are each friends. While they were connected nan trip, Jay was hooking up pinch his wife.”

Are Jay Cutler and Samantha Robertson Still Together?

Jay and Samantha support their narration disconnected societal media – for nan astir part.

In January 2024, Jay shared a beachside photograph while taking a stroll on nan statement pinch Samantha. The mates wrote “Sam [heart] Jay” successful nan soil and the Very Cavallari alum shared nan photograph via Instagram.

Three months later, Samantha was featured successful a station shared connected Instagram via Outsider, Jay’s business. In nan video, Samantha bared tegument while hunting outdoors.

“Some hunting stories are amended than others. Shoes off, nary pants and longbeard down,” nan caption read. “Our caller semi clothed pro hunter, @samanthajrobertson, pinch a awesome changeable from 45yds.” In nan adjacent slide, Jay questioned Sam arsenic if they were successful an question and reply while successful their car, and asked her really she was hardly clothed while hunting.

“I mean, I did not want this video I posted, but I spot that I’ve mislaid this battle. So, astatine slightest I tin explicate myself. I person very viable reasons for why I person nary pants aliases shoes on,” Sam said successful nan video.

She later added, “From nan beginning, we went retired early morning, heard a bunch of gobbles. All right, accelerated guardant to – we sewage a small antsy. We went out, decided if we could perceive anything.
We went to spell and telephone successful nan day for illustration 1 ish 2 ish nan hottest clip of nan day. We heard one, we walked astir for rather a spot and we decided to caput to [the bushes].”

On November 8, 2024, Jay shared a photo of him and Samantha astatine nan Yellowstone play 5 premiere. The brace looked fabulous and embraced each different successful nan snapshot. However, fans noticed nan monolithic gem ringing connected Samantha’s engagement finger.

Fans filled nan comments conception of nan station asking if they were engaged. Although they person yet to publically corroborate their engagement, sources told People that they were headed down nan aisle.