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Caleb Williams rumored new girlfriend Ashaley keeps Bears fans guessing with odd post

Is the Chicago superstar quarterback dating the model?
Matt Ryan|
Nov 28, 2025; Philadelphia, Pennsylvania, USA; Chicago Bears quarterback Caleb Williams (18) against the Philadelphia Eagles at Lincoln Financial Field
Nov 28, 2025; Philadelphia, Pennsylvania, USA; Chicago Bears quarterback Caleb Williams (18) against the Philadelphia Eagles at Lincoln Financial Field | Eric Hartline-Imagn Images

Caleb Williams is turning heads on the field for the Chicago Bears, while his rumored girlfriend Ash Kaashh (Ashaley) just caused more mystery about his life off the field with her latest post.

The second-year quarterback out of the USC Trojans where he won a Heisman Trophy in 2022 has Chicago in the playoffs at 11-5 and NFC North champions for the first time since 2018. No matter what, they will host a Wild Card Round playoff game.

The 24-year-old’s skills were just on display during a crazy 42-38 loss at the San Francisco 49ers where it came down to the final play in a heartbreaking loss.

RELATED: Bears QB Caleb Williams causes stir with Instagram model dating speculation

The model and influencer Ash Kaashh, 28, caused a stir when she posted this from the overtime win over the Green Bay Packers the week before.

And doing the Bears claw gesture.

RELATED: Luther Burden’s stunning Bears game thrusts girlfriend Kendall into spotlight

Fans started to piece together they might be dating when she also posted shopping at the same luxury brand store:

On Tuesday, she’d repost on Instagram her fit from the same game while flexing her look at Soldier Field with no caption. It just adds to more mystery to her dating status with Williams to oddly post it again over a week later.

Will she be at the season finale against the Detroit Lions? Stay tuned.

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.

Now, it looks like he’s moved on to another model.

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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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