On Wednesday, February 25, Shailene Woodley was seen in Milan, Italy, spending time with British actor Milo Callaghan during the city‘s fashion week. The 34-year-old actress and the 28-year-old star of The Strangers were photographed walking arm-in-arm, showing a close and friendly connection. During the outing, Woodley was even captured resting her hand on Callaghan’s back as they strolled together through the Italian streets.
The incident marks one of Woodley’s first public appearances following her split from actor Lucas Bravo, best known for Emily in Paris. Woodley’s representative has not commented on the nature of her relationship with Callaghan.
Background on Woodley and Her Recent Relationship Changes
Prior to this Milan outing, Shailene Woodley was romantically linked to Lucas Bravo, with the couple going public in March 2025. Their split was confirmed by PEOPLE in September 2025. A source described their relationship as
“a breath of fresh air for her”
during its course. After their separation, the same source explained,
“There is no drama, or hard feelings. They just have different priorities,”
highlighting an amicable parting between Woodley and Bravo.
Milo Callaghan’s Rising Acting Career
Milo Callaghan began his television career in 2020 with a role in the second season of Starz’s historical drama The Spanish Princess. He has since appeared with Madelaine Petsch in the horror film series The Strangers and made a guest appearance on HBO’s 2024 series Dune: Prophecy. In 2025, Callaghan starred alongside John Slattery and Dan Fogler in the USA Network’s legal drama The Rainmaker, an adaptation of John Grisham’s novel.
Shailene Woodley’s Recent Projects and Future Plans
Aside from her personal life developments, Woodley remains active in her acting career. She featured in the 2025 film Motor City and returned in season two of Hulu’s thriller series Paradise, which premiered in late February 2025. Woodley is also reportedly working on a biopic about 1960s rock icon Janis Joplin, a project she revealed has been in development for seven years during a December 2024 interview on The Tonight Show.
What This Milan Outing Could Mean for Woodley’s Personal Life
Shailene Woodley’s public appearance with Milo Callaghan during Milan Fashion Week may signal a new chapter following her breakup with Lucas Bravo. While no official comment has been made, their visible closeness in Italy has drawn public interest. As Woodley continues to focus on her career and personal growth, this outing might suggest evolving relationships or important social connections forming in this new phase of her life.
