During Milan Fashion Week on February 25, Shailene Woodley was seen walking the cobblestone streets of the Italian city with Milo Callaghan, sparking speculation. This Shailene Woodley Milan outing marks a notable appearance just months after her confirmed breakup with Lucas Bravo, raising interest in her personal life.
Woodley, known for her role in The Fault in Our Stars, showcased a stylish all-black outfit featuring flair pants, a blazer, and ballet flats. Her dark brown hair was styled in loose curls, and she accessorized with a gold handbag. Milo Callaghan, 28, wore dark wash blue jeans paired with a white Henley T-shirt and a black leather jacket, completing his look with matching loafers.
Their evening together comes less than half a year after Shailene’s separation from Emily in Paris actor Lucas Bravo, which was publicly confirmed in September. The pair had been open about their romance, even appearing as a couple in France in March 2025, but abruptly removed traces of each other from their social media shortly after announcing their split.
Previously engaged to Aaron Rodgers before that relationship ended in 2022, Shailene has expressed clear desires for a meaningful connection. Speaking to Bustle in 2024, she shared,
I want to find a person to do life with, and have a family,
and added,
And I want to watch the sunset.
She elaborated on her vision for the future, saying,
I want to be a mom,
and further explained,
My god, I want to cook someone dinner every night and travel the world with them and have pillow talk and celebrate their joys and their purpose and their destinies and have mine also be celebrated.
Still, Shailene emphasizes a patient outlook on love and life, clarifying,
I don’t have a ‘that should have happened by now’ kind of thing,
and shared a hopeful mindset:
I wake up every day and I say out loud, ‘I’m so excited for the magic and miracles that are going to happen today.’
Hollywood’s Most Memorable Relationships Between Co-Stars and More
Romance in the entertainment industry often intertwines with projects and public appearances. Below is a selection of notable celebrity relationships that have sparked interest and offer context to Shailene’s current situation.
Brad Pitt and Juliette Lewis’s Real-Life Romance
Co-starring in two films as tragic lovers, 1990’s Too Young to Die? and 1993’s Kalifornia, Brad Pitt and Juliette Lewis shared a genuine relationship off-screen. Pitt reflected to Vanity Fair in 1995, stating,
There’s some real genius there. I had a great time with her…It was one of the greatest relationships I’ve ever been in. The problem is, we grow up with this vision that love conquers all, and that’s just not so, is it?
Winona Ryder and Matt Damon’s Late-90s Couple Status
Winona Ryder and Matt Damon, introduced by Gwyneth Paltrow, shared a well-regarded relationship throughout the 1990s before splitting in 2000. Damon described Ryder as a great woman during a 2004 interview, while Ryder praised his character in 2009:
Matt couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him.
Cameron Diaz and Justin Timberlake’s Four-Year Relationship
Known for their chemistry at the 2003 Nickelodeon Kids’ Choice Awards, Diaz and Timberlake pursued a relationship lasting nearly four years. When they parted ways in 2007, their statement emphasized continued affection:
mutually and as friends, with continued love and respect for one another.
Alec Baldwin and Kristin Davis’s Past Romance
While Kristin Davis focused on self-love as the most important relationship, she also reflected fondly on dating Alec Baldwin during her time starring on HBO. On the Literally! With Rob Lowe podcast in 2025, she clarified an anecdote about lending money by saying,
Alec Baldwin was so rich by the time I dated Alec Baldwin, I would have never needed to lend Alec $5,000. Oh my God.
David Moscow and Kerry Washington’s Engagement
Kerry Washington appeared on the cover of InStyle Weddings in 2005 when engaged to David Moscow, though they ended their relationship in 2007.
Madonna and Tupac Shakur’s Public Revelation
Madonna confirmed in 2015 that she dated Tupac Shakur in the mid-1990s, explaining on Howard Stern’s show:
I was dating Tupac at the time, and the thing is…he got me all riled up on life in general.
Jake Gyllenhaal and Reese Witherspoon’s Early-2000s Romance
After Reese Witherspoon’s divorce and before marrying Jim Toth, she and Jake Gyllenhaal dated for a couple of years following their collaboration on the 2007 film Rendition. Jake praised Reese, saying,
She is, as I would say about most of the women who I’m close friends with or had relationships in my life, one of the smartest, strongest people I’ve ever met.
Jesse Metcalfe and Scheana Shay’s Mid-2000s Relationship
Scheana Shay detailed her romance with Jesse Metcalfe in her 2025 memoir My Good Side, sharing moments of intimacy:
We would order in dinner with his parents at his house, and—when we were alone—he would play the guitar and serenade me with songs like ‘Hey There Delilah.’ It felt like I was living a real-life fantasy with this guy I’d watched on TV and in movies for years.
Meg Tilly and Colin Firth’s Five-Year Partnership
Before marrying Livia Giuggioli in 1997, Colin Firth was in a long-term relationship with Meg Tilly, with whom he shares a son, William Joseph Firth, born in 1990. Their son also pursued acting, appearing alongside Colin in Bridget Jones’s Baby.
Mandy Moore and Andy Roddick’s Brief Relationship
Mandy Moore courted by tennis star Andy Roddick between 2003 and 2004, described the experience on Howard Stern’s show in 2018:
He broke my heart. I was a kid, he was a kid. I started dating him when I was 18.
Musical and Acting World Intersections: Dave Coulier and Alanis Morissette
The mystery of who inspired Alanis Morissette’s iconic 1995 single Ironic remains unresolved, with Dave Coulier often mentioned as a possible muse. Morissette denied these rumors in the 2021 documentary Jagged, but the speculation still piques interest.
Alanis Morissette and Ryan Reynolds’ Four-Year Relationship
Morissette and Reynolds dated for four years before quietly separating in 2007. Reynolds once commented on their dynamic:
Oh yeah, I love her music. It can be awkward when she walks in and I’m listening to it in my underwear dancing.
January Jones and Jason Sudeikis’s Short-Lived Romance
January Jones briefly dated Jason Sudeikis in 2010, five years before her short relationship with Will Forte.
Minnie Driver and Matt Damon’s Friendship After Dating
The Good Will Hunting co-stars were romantically involved but transitioned to a close friendship. Damon told Oprah in 1998,
I was with Minnie for a while, but we’re not really romantically involved anymore. We’re just really good friends, and I love her dearly….I care about her a lot. We care about each other a lot. It wasn’t meant to be, you know? And if it’s not meant to be, then it’s not meant to be.
Driver responded to the public announcement saying,
It’s unfortunate that Matt went on Oprah. It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate.
Helen Mirren and Liam Neeson’s Early 1980s Connection
The pair met on the set of Excalibur in 1981 and lived together for several years. Neeson fondly recalled their time together, saying,
I should be so lucky and be honored to have spent three or four years with that lady. She’s really something else.
Jeff Goldblum and Laura Dern’s Jurassic Park Romance
Goldblum and Dern began dating after filming Jurassic Park in 1993. Goldblum told The Chicago Tribune,
I was struck, I’d been a big fan of hers. I think she’s an amazing actress, and a spectacular person. I was struck from the beginning. But after the movie we realized we liked each other.
They got engaged in 1995 but ended their relationship two years later, reuniting professionally in 2022 for Jurassic World: Dominion.
Gillian Anderson and Peter Morgan’s Partnership
Gillian Anderson was romantically linked to The Crown creator Peter Morgan from 2016 until 2020. Anderson earned an Emmy in 2020 for portraying Margaret Thatcher in the Netflix series.
David Arquette and Ellen Barkin’s On-Set Relationship
David Arquette reported dating Ellen Barkin during the filming of their 1995 Western, Wild Bill.
Jeremy Sisto Confirms Dating Reese Witherspoon
In a 2015 Reddit AMA, Jeremy Sisto revealed he once dated Reese Witherspoon. They shared the set of the 1992 TV movie Desperate Choices: To Save My Child. He said,
She was my first actress girlfriend. We had a long distance relationship for a long time. I was so into her.
Bethenny Frankel and Eric Stonestreet’s Brief Relationship
Reported in 2015, the relationship between Real Housewives of New York star Bethenny Frankel and Modern Family actor Eric Stonestreet ended by 2016.
Regina King and Malcolm-Jamal Warner’s Years Together
King and Warner dated for several years before parting ways in 2013. Warner is best known for his role as Theo Huxtable on The Cosby Show.
Kelly Preston and George Clooney’s Late 1980s Relationship
Before her marriage to John Travolta, Preston and Clooney shared a relationship starting in 1987. They lived together and had a pet potbellied pig named Max, but ended things in 1989.
Val Kilmer and Cher’s 1980s Romance
Following her divorces, Cher dated Val Kilmer during the 1980s, a period when Kilmer was rising to fame with films like Top Gun.
Seal and Tyra Banks’ Relationship Before Heidi Klum
The musician Seal dated supermodel Tyra Banks before his later high-profile marriage to Heidi Klum.
Meagan Good and Joseph Gordon-Levitt’s Brief Dating Period
After meeting on the set of the 2005 film Brick, Good and Gordon-Levitt dated for roughly six months.
Joshua Jackson and Rosario Dawson’s Early 2000s Romance
Jackson and Dawson, both prominent actors in the early 2000s, dated for about a year in 2002.
Chris O’Donnell and Reese Witherspoon’s Early Relationship
Before Reese Witherspoon’s rise to stardom, she dated Chris O’Donnell in 1993 shortly after moving to Los Angeles.
Sarah Jessica Parker and Robert Downey Jr.’s Relationship Challenges
Robert Downey Jr. acknowledged that substance abuse played a role in ending his seven-year relationship with Sarah Jessica Parker. He reflected in a 2008 interview,
I liked to drink, and I had a drug problem, and that didn’t jibe with Sarah Jessica, because it is the furthest thing from what she is. She tried to help me. She was so miffed when I didn’t get my act together.
Matthew Perry and Heather Graham’s Short-Lived Flirtation
The late Friends star Perry reportedly had a brief relationship with Heather Graham in 2003, which did not develop further.
Tom Hiddleston and Kat Dennings’ Brief 2010 Romance
Dating for a short period after meeting on the set of a Marvel film, Hiddleston and Dennings appeared close during Comic-Con 2010, though their relationship ended before the film premiered in 2011.
Shailene Woodley’s recent outing in Milan alongside Milo Callaghan fits within a long history of celebrities finding connection both on and off screen, often amid intense public scrutiny. As Woodley continues to navigate her personal life with openness and hope, observers await what may unfold next for the actress on and beyond the fashion week runways.
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