Caleb Williams and Madelyn Cline are fueling dating rumors as the two were seen together at Summer Smash in Illinois over the weekend.

The video that began circulating online was of the Chicago Bears quarterback and the actress enjoying a Sexxy Red set at Summer Smash.

While they appear in the video together, they were not alone enjoying the “SkeeYee” rapper's set as they appeared to be with a group of friends.

The video of Cline and Williams follows breakup rumors with his high school sweetheart, Alina Thyregod. The first overall 2024 NFL Draft pick was seen without his girlfriend during the F1 Miami Grand Prix weekend last month, which is when the rumors began to swirl. While Williams has not addressed a breakup between the two, Thyregod has seemingly deleted all photos and videos of the quarterback from her social media.

Caleb Williams Dating History

Chicago Bears, Caleb Williams

Williams has had two public relationships with women he met during high school. He began dating Valery Orellana in 2020 and their relationship went public when they shared their prom photos together. Williams wen to
Gonzaga College High School, while Orellana attended Richard Montgomery High School.

They were seemingly still an item in 2022 as well according to a since-deleted photo of the two at a USC football game, according to Us Weekly. However, two years later, Williams stunned fans when he made his red carpet debut at the 2024 NFL Draft with his new girlfriend, Alina Thyregod.

The couple has at least been dating since last year but now with the video with Cline its unsure if the high school sweethearts are still together.

Madelyn Cline Dating History

Pete Davidson and Madelyn Cline with hearts around them

Article Continues Below
More Celebrity News
Ice Spice Taylor Swift Travis Kelce
Ice Spice gives insight on Taylor Swift, Travis Kelce friendshipAutumn Hawkins ·
Riley Gaines Simone Biles
Riley Gaines reacts to Simone Biles deactivating X account after feudAutumn Hawkins ·
Kevin Durant attends a WNBA game between the Atlanta Dream and LA Sparks at Crypto.com Arena.
Kevin Durant, Lil B resurrect decade-long beef after Rockets tradeAutumn Hawkins ·
Cincinnati Bengals star Joe Burrow and The Rizzler.
Joe Burrow, The Rizzler create ‘aura overload’ with viral postAndrew Korpan ·
Part owner of the Las Vegas Raiders Tom Brady, who won the first Fanatics Games at the 2025 Fanatics Fest event, on a red carpet.
Tom Brady wins $1 million with latest championshipAndrew Korpan ·
Rutgers Scarlet Knights guard Ace Bailey (4) during the second half against the USC Trojans at Jersey Mike's Arena.
Pennsylvania Governor Josh Shapiro sends 76ers a ‘no Ace Bailey’ demandBenedetto Vitale ·

Cline famously dated her Outer Banks costar Chase Stokes whom they were romantic interests of one another in the show. Fans suspected that they had some onscreen chemistry and in 2020 they went Instagram official.

“It’s really cool…It’s cool to share this experience with your favorite people and also your favorite person…I feel very happy,” she told Entertainment Tonight in 2020.

Cline shared that their relationship working with one another made their romance grow.

“I think because we were friends before this; we understood how we worked as individuals before we were seeing each other,” she added. “We knew how we worked professionally, and we knew each other’s personal boundaries…As a rule, we never bring anything negative to set. If there’s a disagreement or a conversation that needs to be had that could potentially rain on the parade for that day, that’s never something that happens before work.”

Stokes and Cline broke up in 2021 due to their busy schedules.

After Stokes, she dated lead singer of North of Nine, Jackson Guthy in July 2022 and later confirmed in December 2022. In July 2023, Cline unfollowed Guthy according to Elle but they never spoke about a split publicly.

Two months later she was romantically linked to Saturday Night Live alum, Pete Davidson. Their relationship lasted for almost a year but were not seen together after January 2024 in public. It was later reported that the two had broken up after being together on-and-off for 10 months. “Things have fizzled out and they are no longer seeing one another,” a source told Entertainment Tonight at the time.

Cline has spoken about keeping her love life private and if Williams and her are dating, the public most likely won't know for some time.

“Some people can do it,” she told the Today show in 2023 about putting your love life out in the public. “[But] if you give everything, like, 100 percent of your energy, away, where’s the rest for yourself? You finally understand why people in the public eye keep their circles small.”

She continued, “I realized there are parts of my life that only me or one other person are entitled to. I prefer it that way. It also just makes things more special. That’s usually how relationships are.”