Celebrity News February 26, 2026
Shailene Woodley & Milo Callaghan Spark Dating Rumors
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Romance rumors are swirling about Shailene Woodley, 34, and "The Rainmaker" star Milo Callaghan, 28!
The two were spotted together during Milan Fashion Week.
At one point, Shailene was seen with her hand on Milo’s butt as they walked into a building together.
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For their outing together, Shailene opted for an all-black ensemble, while Milo wore blue jeans, a white henley, and a leather jacket.
Woodley made time for Callaghan amid her promo tour for the second season of the hit show “Paradise.”
“Extra” recently spoke with Shailene about working with the show’s star Sterling K. Brown.
The sighting of Shailene and Milo comes months after she called it quits with “Emily in Paris” star Lucas Bravo.
In September, a source told People magazine, "There is no drama, or hard feelings. They just have different priorities.”
Shailene Woodley & Lucas Bravo Split (Report)
View StoryShailene and Lucas also deleted pictures of each other from their Instagram accounts.
