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Actress and producer Shailene Woodley has fueled speculation about a new romance after being seen with British actor Milo Callaghan on February 25 in Milan, Italy, during fashion week. The pair were spotted walking closely together on the city’s cobbled streets, attracting attention amid the stylish atmosphere of one of the world’s top fashion events. The appearance marks a notable moment for those following Shailene Woodley Milo Callaghan news, highlighting their potential connection.
Details of the Milan Sighting
During their public outing, Woodley, 34, chose a chic all-black look, combining flair pants with a blazer and ballet flats, completing her outfit with a gold handbag. Callaghan, aged 28, sported a casual but edgy style, wearing faded denim jeans, a white Henley t-shirt layered under a black leather jacket, and matching loafers. Their coordinated but contrasting ensembles caught the eye as they strolled arm-in-arm, suggesting a comfort and closeness that has sparked rumors about their relationship.
Background on Shailene Woodley’s Previous Relationships
Shailene Woodley’s romantic history includes a relationship with Australian–Fijian rugby player Ben Volavola from 2018 until 2020. Following that, she was engaged to NFL quarterback Aaron Rodgers for about a year before ending the engagement in February 2022. More recently, Woodley dated French actor Lucas Bravo until roughly six months ago. The breakup was amicable, with an insider noting there was “no drama or hard feelings” and that their separation resulted from “different priorities.” Throughout these experiences, Woodley has expressed hope and openness about future partnerships.
Profile of Milo Callaghan in the Spotlight
Milo Callaghan, who was born in October 1998 in the North West of Britain, grew up sharing his childhood with three brothers. He pursued his passion for acting by studying drama at the University of Cambridge, influenced by his mother’s background as a trained theater actress from the Conservatoire in Glasgow, Scotland. Reflecting on his early immersion in theater, Callaghan told 5 Eleven in October 2025 that “theater was all around me,” which deeply shaped his career aspirations.
“I always knew I was going to act, even if it wasn’t professionally. At Cambridge, I became very involved with drama and put on some wonderful plays with wonderful people.” – Milo Callaghan, Actor
He contacted agents during his university years, leading to his first agent discovery after a show at Edinburgh. Callaghan described that moment as one when his agent, Josh, approached him after the performance to introduce himself.
“In my second year, I decided to reach out to some agents and wrote to two or three of them. I was doing a show at Edinburgh a year later, and one of them – my agent, Josh – came up and introduced himself after the show.” – Milo Callaghan, Actor
Career Milestones Leading to Recognition
Callaghan made his screen debut with the 2020 television series The Spanish Princess and progressed to appear in FBI: International (2022), Doctor Who (2024), and Rivals (2024). His roles have also included supporting parts in the horror franchise The Strangers, as well as films such as Dune: Prophecy. However, his breakthrough came with the lead portrayal of Rudy Baylor in the 2025 USA Network/Apple TV legal drama The Rainmaker, adapted from John Grisham’s novel.
The Rainmaker marked a significant step for Callaghan, not only for its prominence but also because the novel had been made into a well-known 1997 film starring Matt Damon. Callaghan reflected on following in those footsteps and the inspiration he drew from his predecessor.
“It was just a privilege to stand on the shoulders of those two fantastic pieces of work: an exciting, beautifully paced novel, and then to follow the movie and try to do something new. That was Matt Damon when he wasn’t quite Matt Damon yet. He’s one of my heroes. I think he’s incredible. That never felt like pressure. It just felt like inspiration…” – Milo Callaghan, Actor
He described the role as both a personal and emotional journey, noting that the character’s ten-hour screen arc involves a significant coming-of-age transformation.
“It had been a personal journey with the experience of taking on a show like that, and also an emotional journey because the character spends 10 hours coming of age.” – Milo Callaghan, Actor
Milo Callaghan’s Perspective on His Acting Career
When discussing his approach to the industry, Callaghan emphasized choosing quality work over the quantity of roles. He pointed out the challenge of balancing exciting opportunities with selective decision-making about his career path.
“I’m on a less is more vibe, partly because I think the work is more important than continuing to work, if that makes sense – I hope that doesn’t sound pretentious. This show has offered a lot of incredible opportunities.” – Milo Callaghan, Actor
“Striking the balance between curating those opportunities and just saying yes to everything and throwing myself into it has been an interesting tight rope to walk. There are a few really exciting opportunities that are spinning in my orbit right now, and I’m just working out which one of them it will be.” – Milo Callaghan, Actor
Insights into Personal Life and Future Hopes
Unlike Woodley, Callaghan has kept his personal life private, rarely sharing details publicly. Meanwhile, Woodley has been open about her desires for the future, emphasizing love, family, and shared experiences in a 2024 interview with Bustle.
“I want to find a person to do life with, and have a family. And I want to watch the sunset. I want to be a mom. My god, I want to cook someone dinner every night and travel the world with them and have pillow talk and celebrate their joys and their purpose and their destinies and have mine also be celebrated.” – Shailene Woodley, Actress
Woodley, currently starring in the second season of the series Paradise, has expressed that she does not feel pressured by societal timelines for relationships. Instead, she embraces a hopeful outlook, looking forward to “the magic and miracles” that life holds without a
“should have happened by now kind of thing.”
Current Status of the Rumored Relationship
As of this writing, neither Shailene Woodley nor Milo Callaghan have publicly commented on the rumors fueling speculation about their romance. Their recent appearance together in Milan remains the primary source fueling curiosity among fans and media alike, leaving the future of their connection open to observation.
'The Rainmaker' star Milo Callaghan stuns for JW ANDERSON pic.twitter.com/9UGA6SVnjd
— MEN (@MENin4K) January 16, 2026