Shailene Woodley'S Milan Walk With Milo Callaghan Sparks Buzz Post-Lucas Split

Shailene's Italian Stroll with a New Face

Love is in the air – or at least that’s what it looked like when Shailene Woodley was spotted taking a casual stroll in Milan with British actor Milo Callaghan. On February 25, the "Big Little Lies" star embraced the romantic vibe of Italy's fashion capital, arm-in-arm with Callaghan amidst the bustling backdrop of Milan Fashion Week. Their outing definitely turned heads as the duo enjoyed each other’s company, with Shailene playfully resting her hand on Callaghan's back, suggesting a blossoming connection.

Reflecting on Past Romances

This comes after Woodley's recent breakup with Lucas Bravo, whom she dated from March to September 2025. The "Emily in Paris" actor was reportedly a refreshing change for Shailene, as a source revealed, "There is no drama, or hard feelings. They just have different priorities." It's clear that while her relationship with Bravo was short-lived, it was a meaningful chapter for Woodley.

Milo Callaghan: Rising Star at Shailene's Side

Milo Callaghan, known for his roles in "The Strangers" series and the legal drama "The Rainmaker," made his debut in "The Spanish Princess" in 2020. His recent projects include working alongside Madelaine Petsch and a guest appearance on HBO's "Dune: Prophecy." His rising career parallels Woodley's own busy schedule, as she juggles her role in Hulu's "Paradise" and develops a biopic on Janis Joplin.

With Milan's fashion scene as their backdrop, Shailene and Milo's outing has certainly sparked curiosity about what's next for this potential duo. Stay tuned to see if this fashionable pair will become Hollywood’s next hot item!