Shailene Woodley has reignited talk of new relationships after being seen with actor Milo Callaghan in Milan on February 25. This encounter has fueled the latest Shailene Woodley dating rumors, occurring five months after her public breakup with Lucas Bravo. During their outing, the pair appeared close, walking arm in arm and later sharing a casual gesture of Woodley resting her hand on Callaghan’s back.
Recent Relationship History Precedes New Sightings
The 34-year-old actress and 28-year-old Callaghan’s sighting follows the end of Woodley’s relationship with Bravo, 37, which faded after public appearances earlier in 2025. Their romance had briefly captured media attention after moments of intimacy in March but dissolved by September. Prior to Bravo, Woodley had been engaged to NFL star Aaron Rodgers, marking another chapter in her personal life that attracted considerable media focus.
Reflecting on Past Engagements and Breakups
Woodley and Rodgers’ engagement officially became public after they confirmed a relationship that began during the onset of the COVID-19 pandemic. Woodley shared on The Tonight Show Starring Jimmy Fallon in February 2021,
“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,’”
followed by,
“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, the couple had ended their engagement, though Rodgers expressed gratitude for their time together. He wrote on Instagram,
“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,”
and added,
“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.”
Insights on Emotional Growth and Moving Forward
According to sources familiar with Woodley’s personal life, the actress found the end of the engagement difficult, contrasting with Rodgers’ smoother transition. An insider stated,
“Ultimately, Shailene was not happy in the relationship.”
Meanwhile, Rodgers has since remarried, choosing to keep his current partner private.
Woodley herself has openly discussed the complexities of love and heartbreak. In an interview with Bustle in September 2024, she admitted,
“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 further reflected,
“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.”
Looking Ahead: What This Means for Woodley’s Personal Life
As speculation continues regarding Woodley’s relationship with Milo Callaghan, it highlights the actress’s journey through love, growth, and self-discovery amid public attention. Her experiences with both Lucas Bravo and Aaron Rodgers demonstrate her openness to vulnerability and learning from past relationships. The public’s interest in Woodley’s dating life is likely to persist as she navigates new connections, and the current Milan sighting suggests fresh chapters may be unfolding.
