Jay Cutler has officially entered his boyfriend era with Samantha Robertson.
The former NFL star hard-launched his relationship via social media in September 2023, years after his divorce from Kristin Cavallari. Cutler and Cavallari were together for 10 years before announcing their split in 2020. They share three kids.
While neither Cutler nor Robertson have publicly confirmed their relationship status thus far, Robertson shared several Instagram photos of the duo looking pretty loved up.
“Vive la France 🇫🇷Congratulations @chanelhandel @amackenzietemplar,” Robertson wrote alongside a pic with her arm wrapped around Cutler at a September 2023 wedding. “The most beautiful wedding ❤️.”
Days later, Robertson dropped another photo of herself and Cutler.
“Sunsets in Montana never disappoint 🫶🏼” she captioned the snap. Cutler commented, “When are we going back?”
When another commenter wrote “I love, love,” Cutler responded, “Don’t we all ❤️.”
The Messenger was first to report in early September 2023 Roberston and Cutler were a couple, with a source revealing that they had been “dating for a while.” The insider added that “their kids have also met.”
Keep reading for everything to know about Cutler’s new girlfriend:
1. Robertston Is a Divorcee
She was previously married to Trace Ayala. While it’s unclear when they split, Robertson was last featured on Ayala’s Instagram in February 2022.
“The road goes on forever and the party never ends!!!!” he wrote, when celebrating Valentine’s day.
Robertson, for her part, last featured Ayala on her Instagram in November 2019.
“I know you never asked to be the worlds best dad and husband but you’re absolutely crushing it!” she wrote at the time.
2. Robertson Has 2 Daughters
Throughout their time together, Robertson and her ex-husband welcomed two daughters, Sophia and River, who make frequent appearances on her Instagram.
3. Robertson Has a Surprising Connection to Justin Timberlake
Her ex-husband, Ayalaa, is the “Creative Director to Mr. Timberlake,” per his X (formerly Twitter) bio.
Alaya and Timberlake’s parents were friends from high school and welcomed their sons within three months of each other. “They did, and still do, everything together,” a GQ article read of the pair, and even launched the William Rast brand together.
Robertson, for her part, showed support for Timberlake by reposting one of his Instagram videos in January 2018.
4. Robertson Has Other Famous Friends
Other than her connection to Timberlake, it appears that Robertson has a bond with some other celebrities. Rita Ora, for one, follows Robertson on Instagram. Robertson also shared photos from a January 2022 vacation featuring former NASCAR driver Clint Bowyer and his family.
5. Australia Is Robertson’s ‘Home’
“Home is where the heart is 🇦🇺 Family is priceless and health is wealth,” Robertson captioned an Instagram post from November 2022. “Missing you all already!”
