shailene woodley sparks romance with milo in milan stroll

Shailene Woodley and Milo Callaghan were spotted together on February 25 during Milan Fashion Week in Italy, marking a new chapter in Woodley’s personal life amid the city’s famed cobblestone streets. This public appearance highlights the evolving romance between the two actors, attracting attention as Shailene Woodley Milan Fashion events tend to do.

The Fault in Our Stars star, 34, showcased a chic, all-black look featuring flare pants, a blazer, and ballet flats, accessorized by a gold handbag. She wore her dark brown hair in loose curls. Milo Callaghan, 28, complemented her style with dark wash blue jeans, a white Henley T-shirt, and a black leather jacket paired with loafers.

This outing comes less than six months after Shailene’s split from Lucas Bravo, known for his role in Emily in Paris, which was publicly confirmed in September following a brief romance. Although the pair had openly displayed their relationship with outings in France as recently as March 2025, they chose to remove each other from social media soon after their break-up.

Prior to her romance with Lucas, Woodley was engaged to Aaron Rodgers before ending the relationship in 2022. In interviews, she has expressed her clear vision for future relationships, emphasizing that she seeks lasting happiness rather than simply settling.

I want to find a person to do life with, and have a family,

she revealed in a 2024 conversation with Bustle.

And I want to watch the sunset.

Shailene further elaborated on her aspirations, stating,

I want to be a mom,

and added,

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.

Despite these clear desires, she remains patient about the timing of these milestones.

I don’t have a ‘that should have happened by now’ kind of thing,

she said, continuing,

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 Couples Who Found Unexpected Romance

Shailene Woodley and Milo Callaghan’s new connection echoes other celebrity romances where sparks ignited unexpectedly. Here is a look at some notable Hollywood couples who experienced intense, often brief relationships, highlighting the complexities of love in the public eye.

Brad Pitt’s Relationship with Juliette Lewis

Brad Pitt and Juliette Lewis portrayed doomed lovers in the films Too Young to Die? (1990) and Kalifornia (1993), but their real-life romance was notably positive. Pitt accompanied Lewis to the 1992 Oscars after her nomination for Cape Fear. Reflecting in a 1995 Vanity Fair interview, Pitt said,

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.

However, he also acknowledged the challenges of idealistic love, stating,

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 End of an Era

Winona Ryder and Matt Damon, introduced by Gwyneth Paltrow, were a couple through the 1990s until their breakup in 2000. Damon praised Ryder in a 2004 Playboy interview as a great woman, while Ryder told Black Book 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 Respectful Split

Cameron Diaz and Justin Timberlake began dating after an onstage moment at the 2003 Nickelodeon Kids’ Choice Awards. Their nearly four-year relationship ended in 2007 amicably. Upon their breakup, they released a statement affirming their continued friendship, describing it as,

mutually and as friends, with continued love and respect for one another.

Kristin Davis and Alec Baldwin’s Amusing Distance

Sex and the City’s Kristin Davis reflected humorously on her relationship with Alec Baldwin during a 2025 podcast with Rob Lowe. She clarified that a mystery man who once borrowed $5,000 was not Baldwin, 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 Brief Engagement

Scandal star Kerry Washington appeared on the cover of InStyle Weddings in 2005 when she was engaged to David Moscow, but the pair ended their relationship by 2007.

Madonna’s Revelation About Tupac Shakur

Madonna addressed rumors about dating rapper Tupac Shakur during a 2015 interview, recalling,

I was dating Tupac at the time, and the thing is…he got me all riled up on life in general.

Tupac’s life was tragically cut short in 1996 at age 25.

Jake Gyllenhaal and Reese Witherspoon’s Admiration

Reese Witherspoon and Jake Gyllenhaal dated after starring together in the 2007 thriller Rendition. Gyllenhaal spoke highly of Witherspoon, calling her,

one of the smartest, strongest people I’ve ever met.

Jesse Metcalfe and Scheana Shay’s Memoir Memories

Scheana Shay revealed in her 2025 memoir My Good Side that she dated Jesse Metcalfe during the mid-2000s. She fondly recalled romantic moments, writing,

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.’

She added,

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: A Family Connection

Before his marriage to Livia Giuggioli, Colin Firth dated Meg Tilly for five years. Their son, William Joseph Firth, born September 20, 1990, is also an actor who appeared alongside his father in Bridget Jones’s Baby.

Mandy Moore’s Early Heartbreak with Andy Roddick

Mandy Moore dated tennis star Andy Roddick from 2003 to 2004 but described the relationship candidly on Howard Stern’s show in 2018, saying,

He broke my heart. I was a kid, he was a kid. I started dating him when I was 18.

Dave Coulier and Alanis Morissette’s Musical Mystery

The inspiration behind Morissette’s 1995 hit “Ironic” remains debated, with Full House star Dave Coulier frequently mentioned as a possible muse. Morissette denied this in the 2021 documentary Jagged, yet the question remains intriguing among fans.

Alanis Morissette and Ryan Reynolds’ Polite Parting

Ryan Reynolds praised his then-fiancée Morissette in 2005, saying,

Oh yeah, I love her music, It can be awkward when she walks in and I’m listening to it in my underwear dancing.

Although amicable, their relationship ended in 2007 after four years.

January Jones’ Brief Romance with Jason Sudeikis

January Jones dated comedian and actor Jason Sudeikis for several months in 2010, years before her later brief relationship with Will Forte.

Minnie Driver and Matt Damon’s Friendship After Romance

Once a couple, Minnie Driver and Matt Damon parted ways but maintained a close friendship. Damon explained on The Oprah Winfrey Show in January 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… It wasn’t meant to be, you know? And if it’s not meant to be, then it’s not meant to be.

Driver later commented,

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 Years

Helen Mirren and Liam Neeson met on the set of 1981’s Excalibur and lived together before separating in the mid-1980s. Neeson expressed admiration in a 2023 interview, 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

Jeff Goldblum and Laura Dern began dating after filming Jurassic Park in 1993. Goldblum remarked to The Chicago Tribune that he was captivated from the start, calling Dern “an amazing actress” and “a spectacular person.” The couple got engaged in 1995 but separated two years later. They reunited on screen in 2022’s Jurassic World: Dominion.

Gillian Anderson’s Relationship with Peter Morgan

The X-Files alum was partnered with The Crown creator Peter Morgan from 2016 to 2020. Anderson won an Emmy for her portrayal of Margaret Thatcher in the Netflix series during their time together.

David Arquette and Ellen Barkin’s On-Set Romance

David Arquette and Ellen Barkin reportedly dated while working on their 1995 Western Wild Bill.

Jeremy Sisto and Reese Witherspoon’s Early Relationship

Jeremy Sisto revealed during a 2015 Reddit AMA that he dated Reese Witherspoon while filming the 1992 TV movie Desperate Choices: To Save My Child. He described,

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 Couplehood

E! News announced in 2015 that Real Housewives of New York’s Bethenny Frankel and Modern Family’s Eric Stonestreet were dating. The pair split the following year.

Regina King and Malcolm-Jamal Warner’s Long-Term Relationship

Regina King and Malcolm-Jamal Warner, known for his role as Theo Huxtable on The Cosby Show, dated for several years before ending their relationship in 2013.

Kelly Preston’s Early Life with George Clooney

Before marrying John Travolta, Kelly Preston and George Clooney lived together during the late 1980s, sharing memories including caring for a potbellied pig named Max. They parted ways in 1989.

Val Kilmer and Cher’s 1980s Romance

Val Kilmer and Cher dated in the 1980s after Cher’s divorces from Sonny Bono and Gregg Allman, blending the legendary diva with the rising star of Top Gun.

Seal and Tyra Banks’ Relationship Before Heidi Klum

Before becoming Heidi Klum’s ex, musician Seal dated supermodel Tyra Banks, adding a different chapter to his personal life.

Meagan Good and Joseph Gordon-Levitt’s Short-Lived Love

Meagan Good and Joseph Gordon-Levitt reportedly dated for about six months after meeting on the set of the 2005 film Brick.

Joshua Jackson and Rosario Dawson’s Year Together

Joshua Jackson and Rosario Dawson, notable for their roles in Dawson’s Creek and Josie and the Pussycats, dated for approximately a year in 2002.

Chris O’Donnell and Reese Witherspoon’s Early Hollywood Days

Chris O’Donnell and Reese Witherspoon were romantically involved in 1993 when Witherspoon was just 17 and had recently moved to Los Angeles.

Sarah Jessica Parker and Robert Downey Jr.’s Challenging Past

Robert Downey Jr. admitted the difficulties of his relationship with Sarah Jessica Parker, citing substance abuse as a major cause of their breakup. In a 2008 Parade interview, he confessed,

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 Brief Romantic Encounter

Matthew Perry and Heather Graham reportedly had a short fling in 2003, which, while brief, added to the celebrity dating landscape of the time.

Tom Hiddleston and Kat Dennings’ Short-Lived Marvel Romance

Tom Hiddleston and Kat Dennings briefly dated in 2010, appearing together at Comic-Con to promote Thor, though their relationship ended by the film’s premiere the following year.

Shailene Woodley’s public outing with Milo Callaghan during Milan Fashion Week not only captures media attention on their budding relationship but also reflects her enduring commitment to finding meaningful love on her own terms. As the couple’s story develops against the backdrop of Milan’s fashion scene, fans will be watching for how this romance evolves amid their demanding careers and personal aspirations.

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