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Who Is Shailene Woodley Dating? What’s Confirmed About Milo Callaghan

Shailene Woodley has been linked to Milo Callaghan after a Milan sighting, but no current relationship has been publicly confirmed.
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No current relationship has been publicly confirmed in the latest reporting reviewed. Shailene Woodley has been linked to actor Milo Callaghan after the two were seen together in Milan in February 2026, but the reports do not establish that they are dating.

What is known about Shailene Woodley’s relationship status?

Woodley’s current relationship status is not publicly confirmed. A February 2026 Milan sighting and reports that she and Callaghan are co-stars in the upcoming film Mother’s Helper prompted speculation, but neither fact confirms a romance. Cosmopolitan’s May 7, 2026 report treats the possibility as uncertain; it does not report confirmation from either actor.

That distinction matters: being seen together or working on the same film is not proof of a relationship. Anonymous tipster accounts repeated in coverage also do not amount to confirmation.

Who was Shailene Woodley’s most recently reported partner?

Actor Lucas Bravo, known for Emily in Paris, is the most recently reported former partner in the available relationship timeline. ELLE says Woodley and Bravo were first linked in March 2025 and that their relationship ended in September 2025. People quoted an unnamed source describing the breakup as amicable and saying the pair had different priorities; that characterization is the source’s account, not a statement from Woodley or Bravo.

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How did Woodley’s earlier relationships unfold?

Nahko Bear, 2014–2016

ELLE reports that Woodley was linked to Nahko Bear, frontman of Nahko and Medicine for the People, during this period. This is part of her reported dating history, not evidence about her current status.

Ben Volavola, 2018–2020

Woodley and rugby player Ben Volavola attended the Adrift premiere together in 2018, and ELLE reports that their relationship lasted until 2020. In a 2020 Bustle cover story, Woodley reflected that she had been in a relationship moving toward marriage and children, but realized she was not ready to commit to that future.

Aaron Rodgers, 2020–2022

Woodley and NFL quarterback Aaron Rodgers were first linked in 2020 and announced their engagement in February 2021. ELLE reports that the engagement ended in 2022. Speaking to Outside in 2024, Woodley said: “I haven’t shared much about my relationship with Aaron because it always makes me cry. It was not right. But it was beautiful.”

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What did Aaron Rodgers say about their relationship in 2026?

On September 10, 2026, Rodgers discussed the former engagement on the Not Just Football podcast. Just Jared reported his account, including his remark, “I date Shailene, I propose and she says yes.” These are Rodgers’s statements about a past relationship, not a jointly verified account of private events, and they do not establish Woodley’s present relationship status.

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The Broken Hearts Club: A Romantic Comedy
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