Is 24-Year-Old Caleb Williams Dating 4 Years Older Model, Ash Kaashh? She Shares Date Night Pictures

Caleb Williams is an American football player for the Chicago Bears in the National Football League. He is known for his record-breaking game skills. He was selected by Chicago in the 2024 NFL draft and set several franchise passing records. His career highlights include his remarkable tenure at USC, where he won the 2022 Heisman Trophy, and his transition to the NFL, where he continues his journey as a professional footballer. Regarding his personal life, reports suggest he may be dating a four-year-older influencer.

Caleb Williams is dating a four-year-old influencer, Ash Kaashh?

So far, Caleb Williams has kept his personal life private. The 24-year-old is not yet married and talking about his girlfriend, many wonder if he is dating model and influencer, Ash Kaashh. Recently, Ash (Ashaley) responded to a fan about the Chicago Bears game, which grabbed a lot of eyeballs. Many think that Caleb and Ash are romantically involved.

The mystery deepened last month, after Ashaley shared a post from the game night in December 2025, where she did the bear claw hand gesture. She was dressed up in a fuzzy coat and a matching hat. Along with it, she wrote, "Dressed like our man moving crack in the 80’s," as she posed with another woman. The post exploded within hours and gained a lot of traction, reaching over 3 million people, who liked it. 

Now, Ashaley shared a cryptic post that left her fans wondering if it was an indication of her romantic linkup with Caleb Williams. The influencer responded to a fan who wrote, "Anyone having people over to watch the @ash.kaashh Bowl tonight?" The post was referring to Chicago Bears' recent game. Ashaley quickly responded with "Lmfaoooooooo". Ashley also shared a glimpse of her date night, leaving many wonder if she was with Caleb. 

Caleb Williams past relationship

For the unversed, Caleb Williams started the season as a single man after he dated model Alina Thyregod. The ex-couple met while they were studying at Gonzaga College High School. They were together for almost two years and marked their one-year anniversary on October 22, 2024. Once in an interview, Caleb talked about his relationship, and said:

"She is from Europe, Danish. She moved from D.C. because her dad had a job in D.C. I met her at the end of her tenure. We dated a little bit. Then we ended it. Kept in strong communication throughout four years. We’re back-dating again."

As per reports, Caleb Williams' rising career and success hugely impacted his relationship with his girlfriend, Alina Thyregod. Despite trying their best to keep the relationship going, the couple parted ways in 2025. Alina often shares glimpses of her post-breakup life as she enjoys her life on social media. 

On the other hand, Caleb has moved on in life and influencer, Ash Kaashh. As per reports, Caleb William and Ash Kaash share a four-year age gap. According to online records, Kaashh was born in 1997, making her 28 years old, while the famous footballer was born in 2001, making him 24 years old.

What do you think about Caleb Williams' new relationship with Ash Kaashh?

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