Shailene Woodley was photographed in Milan, Italy, on February 25, spending time with British actor Milo Callaghan amid the Milan Fashion Week events. The 34-year-old actress and Callaghan, 28, were seen walking closely arm-in-arm in public, with Woodley resting her hand on the back of Callaghan’s jeans as they strolled together through the city’s streets. This outing marks a notable moment following Woodley’s recent split from her previous partner.
Background on Woodley’s Recent Relationship Status
Woodley was last known to be romantically involved with Lucas Bravo, co-star of the series Emily in Paris. Their relationship became public in March 2025, but PEOPLE confirmed in September 2025 that the couple had ended things. An insider commented that the relationship
“was a breath of fresh air for her,”
but clarified the split by saying,
“There is no drama, or hard feelings. They just have different priorities.”
Milo Callaghan’s Acting Career Highlights
British actor Milo Callaghan began his on-screen work in 2020 with a role in the Starz hit series The Spanish Princess. More recently, he appeared alongside Madelaine Petsch in the slasher films titled The Strangers and had a guest role in HBO’s 2024 series Dune: Prophecy. In 2025, Callaghan co-starred with John Slattery and Dan Fogler in the USA Network legal drama adaptation of John Grisham’s novel, The Rainmaker.
Shailene Woodley’s Current Projects and Future Plans
Woodley remains active in film and television, with her latest movie, Motor City, released in 2025. Additionally, she returned to television in the second season of Hulu’s thriller series Paradise, which premiered on February 23, 2026. Beyond acting, Woodley has been developing a biographical film about legendary 1960s rock singer Janis Joplin—a project she disclosed has been in progress for seven years during a 2024 appearance on The Tonight Show.
Implications of Woodley’s Milan Appearance with Callaghan
Shailene Woodley’s public appearance with Milo Callaghan in Milan comes shortly after her split from Lucas Bravo, signaling possible new developments in her personal life. The images showing their close interaction during an international fashion event have sparked curiosity about the nature of their relationship. As Woodley continues her work in film and television, fans and media alike will likely watch closely for any confirmation of a new romance, while also following her evolving career and creative endeavors.
