Shailene Woodley sparked dating speculation after being spotted with actor Milo Callaghan following her split from Lucas Bravo. Woodley, 34, and Callaghan, 28, were photographed together in Milan on Wednesday, February 25. The duo walked arm in arm during the outing, and later that night, Woodley was seen with her hand on the back of Callaghan’s jeans. The actress stepped out with Callaghan five months after her split from Bravo, 37, made headlines. The pair sparked romance rumors in March 2025 when they were seen getting cozy in public, but the relationship fizzled out by September. Before Br...

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