Shailene Woodley, Milo Callaghan Spark Dating Rumors
February 26, 2026·1 day ago·via extratv.com
Romance rumors swirl around Shailene Woodley, 34, and actor Milo Callaghan, 28, after they get cozy during Milan Fashion Week. The pair draws eyes as Shailene places her hand on Milo's butt while walking into a building together. She rocks an all-black ensemble, while he pairs blue jeans, a white henley, and a leather jacket. Woodley squeezes in the outing amid her promo tour for season two of hit show "Paradise.
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