Are Shailene Woodley and Milo Callaghan Dating? What I Know About Their Potential Showmance
Key PointsShailene Woodley called it quits with Emily in Paris star Lucas Bravo in Sept. 2025.She was then spotted in Milan with Milo Callaghan in Feb. 2026.Now, Deadline reports that they’re starring in the upcoming film, Mother’s Helper. Could they be in a showmance?While some of the internet still mourns Shailene Woodley’s real-life romance with the hot chef in Emily in Paris, it seems like she may be moving on. The Big Little Lies star called it quits with Lucas Bravo back in September, but come February, she was spotted with a new man—and, now, Deadline reports that they’re starring alongside each other in her new movie, Mother’s Helper.Okay, so who is this man, you ask? That’d be up-and-coming actor Milo Callaghan, who recently starred in The Rainmaker. According to photos published by People, Milo and Shailene were spotted hanging out together during Milan Fashion Week on February 26, where she placed her hand on the back of his jeans as they walked side-by-side.Aside from their PDA overseas, DeuxMoi tipsters actually dropped hints that they may have had a meet-cute on the set of Mother’s Helper a few weeks prior.Getty ImagesPer one tip, the pair had “dinner at Delbar in Atlanta,” where they reportedly shot the film. The source claims they “sat at the bar [and were] very cozy and engaging but [there was not any] PDA.” An additional insider “saw them at Harbor Coffee in Atlanta on [February] 8, [and they were] super cuddly in line together!!!”The co-stars were also spotted traveling together by a third source, who caught them on a flight from San Francisco to Paris on February 23, before they made their way to Milan. “At one point [Shailene] was sitting on [Milo’s] lap in his business class seat, [while] nuzzling up to him. [It was] so cute,” they said in their tip.In September, People confirmed Shailene and her ex, Lucas, broke up amicably. “There is no drama, or hard feelings. They just have different priorities,” a source told the outlet at the time.Taking it with a grain of salt, but it looks like Shailene and Milo might be in a showmance. Staying tuned for more on these two!Shailene Woodley and Lucas Bravo’s Ship TimelineSources Weigh In on Shailene and Lucas’ Breakup‘Big Little Lies’ Season 3 Is Finally Happening
