On Wednesday, February 25th, during Milan Fashion Week, Shailene Woodley, 34, was spotted strolling hand-in-hand with British actor Milo Callaghan, 28, in a display of affection that was hard to miss. The pair, who appeared utterly enamored with each other, couldn't keep their arms from circling around each other during their outing. In another snapshot from their night out, Woodley was seen placing her hand on the back of Callaghan's jeans as they walked together, further fueling the fire of their budding romance. A representative for Woodley did not immediately respond to PEOPLE's request for comment.
Woodley was most recently in a romantic relationship with 'Emily in Paris' star Lucas Bravo, whom she first stepped out with in March 2025. However, PEOPLE confirmed their split in September after a source revealed that Woodley and Bravo's relationship was "a breath of fresh air for her" in August. The source further stated that "there is no drama or hard feelings; they just have different priorities."
Callaghan made his on-screen debut in 2020 when he appeared in the second season of the Starz series 'The Spanish Princess.' Most recently, he starred alongside 'Madelaine Petsch' in her slasher movies 'The Strangers' and appeared in one episode of HBO's 2024 series 'Dune: Prophecy.' In 2025, he costarred with 'John Slattery' and 'Dan Fogler' in the USA legal drama 'The Rainmaker,' based on Josh Grisham's novel of the same name.
Meanwhile, Woodley recently appeared on the big screen in the 2025 movie 'Motor City.' She also began starring in season two of Hulu's thriller series 'Paradise,' which returned on February 23rd. The 'Big Little Lies' star is also developing a long-awaited biopic of 1960s rock singer Janis Joplin, which she revealed she had been working on "for seven years now" during a December 2024 appearance on 'The Tonight Show.'
