Caleb Williams’ rumored girlfriend Ashaley gushes over ‘Mr. Make It Happen’

The Chicago Bears franchise has never felt more optimistic than they are right now, and much of that is owed to star 24-year-old quarterback Caleb Williams.

Williams (who completed 24 of 48 passes with 361 yards, 2 touchdownsand 2 interceptions) led the Bears to a 31-27 victory over their division rival, the Green Bay Packers, on January 10. As a result, Chicago will face the Los Angeles Rams in the Divisional round of the NFL playoffs on January 18.

Chicago Bears quarterback Caleb Williams (18) rolls out as Green Bay Packers linebacker Quay Walker on January 10, 2026 — Jan 10, 2026; Chicago, IL, USA; Chicago Bears quarterback Caleb Williams (18) rolls out as Green Bay Packers linebacker Quay Walker (7) applies the pressure during the first half of an NFC Wild Card Round game at Soldier Field. Mandatory Credit: Matt Marton-Imagn Images | Matt Marton-Imagn Images

Williams might be the most beloved athlete in the city of Chicago right now, given his role in turning the franchise around. But there seems to be one Bears fan that he cares about more than the rest.

The former USC Trojans star is rumored to be dating 28-year-old model Ashaley (Ash) Kaashh. While neither has confirmed these rumors directly, much of Ashaley's social media activity leaves little doubt.

Ashaley Kaash's November 14, 2025 Instagram post. | Instagram/@ash.kaash

Ashaley was at the Bears' game last weekend and posted several videos of her leaving Soldier Field after the win.

The song in her Instagram story videos, which is called BLOUSIN by Rob 49, included the lyrics, "Biggest in this -, man," which might have been a reference to Williams.

Caleb Williams’ rumored girlfriend Ashaley drops telling love note before Bears game

Speculation has continued with a recent X post that Ashaley (whose 29th birthday is coming up) made on January 15.

"I Love my Mr. Make it happen 💖💘💖💘💖💘💘💖💘💖💘💖💘💖💘💖💘💖💘💖💘💘💖💘💖💘💖💘💖💘💖💘💖💘💖," she wrote. Bears fans believe this was directed at Williams, which is clear from their comments.

I Love my Mr. Make it happen 💖💘💖💘💖💘💘💖💘💖💘💖💘💖💘💖💘💖💘💖💘💘💖💘💖💘💖💘💖💘💖💘💖💘💖
— ashaley 🦋 (@ash_kaashh) January 15, 2026

What's for sure is that this would be a fitting nickname for Williams, given what he has made happen for Chicago this season.

Ashaley Kaash's January 14 Instagram story. | Instagram/@ash.kaash

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