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 Bravo, Woodley was engaged to Aaron Rodgers. The former couple sparked dating speculation in July 2020, and Rodgers, 42, confirmed their engagement nearly a year later.
Shailene Woodley and Lucas Bravo’s Relationship Timeline
Woodley publicly discussed how their relationship had begun at the beginning of the COVID-19 pandemic.
“It’s kind of funny. Everybody right now is freaking out over [our engagement], and we’re like, ‘Yeah, we’ve been engaged for a while,’” she said during an appearance on The Tonight Show Starring Jimmy Fallon in February 2021. “He’s, first off, just a wonderful, incredible human being. But I never thought I’d be engaged with somebody who threw balls for a living.”
By February 2022, Us Weekly confirmed that Woodley and the NFL star had ended their engagement after a whirlwind romance. The same month, Rodgers praised the time he got with Woodley before their breakup.
“Thanks for letting me chase after you the first couple months after we met, and finally letting me catch up to you and be a part of your life,” he wrote to her via Instagram at the time. “Thanks for always having my back, for the incredible kindness you show me and everyone you meet, and for showing me what unconditional love looks like, I love you and am grateful for you.”
Shailene Woodley’s Dating History: Aaron Rodgers, More
A source told Us in May 2022 that Woodley was “more upset” over the split, while Rodgers seemed “to be moving on” just fine. “Ultimately, Shailene was not happy in the relationship,” the insider noted about Rodgers, who has since gotten married to a partner he has kept out of the spotlight.
Woodley, for her part, reflected on heartbreak, telling Bustle in September 2024, “I fell in love over and over with unavailability. I’m very open as a human. I love easy and I care easy, but I do not love lightly, and I do not care lightly.”
She added: “It’s really taken me a lot of time to understand that it’s not on me to fix or heal or do anything about [a relationship] other than protect the deep care and love that I have for the world and for my people. Ultimately, that has helped me walk away without the need to understand why certain things didn’t play out the way that I may have desired them to.”
