Aaron Rodgers’ ex‑fiancee Shailene Woodley sparks headlines as QB’s Steelers future remains uncertain

Aaron Rodgers is facing a critical offseason decision about his NFL future, and off the field, his past is making headlines again. The 42-year-old quarterback, who helped the Pittsburgh Steelers reach the playoffs in 2025, has yet to confirm whether he will return or retire. Meanwhile, news of his ex-fiancée, Shailene Woodley, appearing with a new partner adds another twist to the story.

Rodgers led the Steelers to a 10-7 record, but their season ended when the Houston Texans eliminated them from the playoffs. As of now, Rodgers is a free agent, having signed a one-year, $13.65 million contract with Pittsburgh last season. The league expects him to announce his decision around mid-March, coinciding with the start of the NFL’s legal tampering period on March 9.

Shailene Woodley steps out with British actor Milo Callaghan

Woodley has been spotted with British actor Milo Callaghan during Milan Fashion Week, marking her first public outing with a new partner since breaking off her engagement to Rodgers in Feb. 2022. The two had been engaged for a short time after dating since 2020.

In an interview with “Outside”, Woodley reflected on their relationship. “I haven’t shared much about my relationship with Aaron because it always makes me cry. It was not right. But it was beautiful,” she said. She revealed that she experienced a difficult period in early 2022, describing it as a time when she felt “like I lost my soul, my self, my happiness, my joy.” She credited her stylist and best friend, Kris Zero, with helping her through those months.

Rodgers, in turn, had posted a heartfelt tribute on Instagram following their breakup. He wrote: “Shailene Woodley, thanks for letting me chase after you the first couple of months after we met, and finally letting me catch up to you and be a part of your life. Thanks for always having my back… I love you and am grateful for you.”

As Rodgers contemplates his next move, Steelers general manager Omar Khan confirmed at the NFL Scouting Combine on Feb. 24 that the team wants him back. “The door’s open to have Aaron back,” Khan said. Former Packers coach Mike McCarthy, now leading the Steelers, has also been in touch, making the Steelers a likely landing spot if Rodgers returns.

Rodgers’ decision will shape both his own legacy and Pittsburgh’s quarterback plans. With Woodley’s new romance in the spotlight, the offseason is proving eventful for both the NFL star and his former fiancée.


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