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Bears QB Caleb Williams causes stir with Instagram model dating speculation

The evidence is there that the 24-year-old NFL superstar could be in a new relationship.
Matt Ryan|
Oct 26, 2025; Baltimore, Maryland, USA; Chicago Bears quarterback Caleb Williams (18) on the field after them game against the Baltimore Ravens at M&T Bank Stadium.
Oct 26, 2025; Baltimore, Maryland, USA; Chicago Bears quarterback Caleb Williams (18) on the field after them game against the Baltimore Ravens at M&T Bank Stadium. | Tommy Gilligan-Imagn Images

Caleb Williams is winning on the field for the Chicago Bears, and now it’s looking like he could be off the field as well with a new girlfriend as dating rumors with an Instagram model are heating up.

The second-year quarterback out of the USC Trojans where he won a Heisman Trophy in 2022 has Chicago in the playoffs at 11-4 and eyeing the team’s first NFC North title since 2018.

He’s coming off an unreal comeback vs. their rivals the Green Bay Packers where he dropped an absolutely dime for a game-winning touchdown in overtime.

RELATED: Caleb Williams seems to troll Lions with Bears linemen's Christmas gift

While he’s winning and loved by Bears fans for what he’s doing for the team, he may have a new love interest in his personal life as well.

Williams broke up with his former girlfriend before the season

Williams, 24, started the season a single man after dating model Alina Thyregod. Williams and Thyregod, who first met as students at Gonzaga College High School, celebrated their one-year anniversary on Oct. 22, 2024, and times appeared to be great between the two.

It didn’t last, however, despite his recent like on her post below.

RELATED: Bears QB’s Caleb Williams adds intrigue with ex-girlfriend Alina’s latest post

Dating another model?

Now, it’s rumored he’s dating 28-year-old model Ash Kaashh (Ashaley), who has 2.7 million followers on IG.

Here’s her doing to claw gesture at the Bears-Packers game that’s being referred to.

They definitely have similarly high-fashion shopping taste, too, hitting the same Bottega store.

Fans are staring to piece it together but Williams looks like he could be dating again.

He’s also focused (hopefully) on a huge game on Sunday Night Football coming up at the San Francisco 49ers.

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Matt Ryan
MATT RYAN

Matt Ryan is a dedicated sports journalist with over 20 years of experience in digital and linear media. After receiving a Masters in Journalism from USC, he’s worked for Fox Sports, NBC Sports, Yahoo Sports, USA Today Sports Media Group, and Bally Sports, while holding various leadership roles along the way.

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