Shailene Woodley Steps Out With Rainmaker’s Milo Callaghan in Italy

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There’s no fault in these stars getting along. 

Shailene Woodley and Milo Callaghan were spotted together in Milan, Italy on February 25th during Fashion Week, as they strolled along the city’s streets.

Shailene Woodley, known from The Fault in Our Stars, wore a stylish black outfit featuring wide-leg pants, a blazer, and ballet flats. She completed the look with a gold handbag and loose, wavy hair. Her co-star, from The Rainmaker, chose a more casual look with dark blue jeans, a white t-shirt, a black leather jacket, and loafers.

Shailene Woodley was recently seen out with Milo Ventimiglia, 28, just months after her September split from actor Lucas Bravo, known for his role in Emily in Paris. Their romance had been relatively brief but quickly gained attention.

After being publicly seen together in France in March 2025, the former couple quickly removed all traces of each other from their social media following their breakup.

Shailene, who was previously engaged to Aaron Rodgers before their split in 2022, told People magazine in April 2025 that she was very happy with Lucas at the time. However, she’s also stated that she wants a truly lasting, happily-ever-after relationship and won’t accept anything less.

In a 2024 interview with Bustle, she shared her desire for a life partner and starting a family, adding that she simply wants to enjoy life’s simple pleasures, like watching the sunset.

In fact, she had a full picture about what she hoped her future holds.

“I really long to be a mother,” she went on. “I dream of making dinner for someone every night, exploring the world with them, sharing quiet moments, and celebrating all of our achievements and dreams together.”

But trust, she’s in no rush for perfection. 

She explained she doesn’t dwell on what should have already occurred. Instead, she starts each day with a positive affirmation, eagerly anticipating good things to come.

For celebrity couples who have found that unexpected magic together, keep reading… 

Oh my gosh, can we talk about Brad and Juliette for a second? They had such chemistry, especially because they played these tragically doomed lovers not once, but twice! First in ‘Too Young to Die?’ back in ’90, and then again in ‘Kalifornia’ a few years later in ’93. It was heartbreaking to watch, honestly. But the best part? Apparently, they were totally great together in real life! It’s just… perfect. They had a genuinely lovely relationship, which makes those roles even more amazing, don’t you think?

Brad Pitt revealed in a 1995 interview with Vanity Fair that he still had feelings for his former partner. He fondly remembered their time together, especially when she was nominated for an Oscar for Cape Fear in 1992, calling it one of the best relationships of his life. However, he also acknowledged that sometimes love isn’t enough, challenging the common belief that it always solves everything.

It wasn’t just a nostalgic fantasy – Ben Affleck and Jennifer Garner really were a couple at the end of the 20th century. The story goes that they met thanks to Gwyneth Paltrow, who famously dated Ben’s close friend, Matt Damon. They ended their relationship in 2000.

You know, looking back at my time with Matt Damon, I’ve always considered him a truly wonderful person. He’s just a genuinely good guy. And he’s always said such kind things about me too – he once called me a ‘great woman’ in an interview. Honestly, we’ve always been on really good terms, and I feel lucky to have that kind of relationship with him. It’s nice when things end amicably, and we definitely have that!

There was a definite spark between Cameron Diaz and Justin Timberlake when they presented together at the 2003 Kids’ Choice Awards. They dated for nearly four years, and their breakup in 2007 was announced with a formal statement emphasizing their continued friendship, love, and respect for each other.

Kristin Davis, known for her role in Sex and the City, says that while self-love is the most important relationship, she still enjoyed dating Alec Baldwin during her time on the HBO show.

During a February 2025 appearance on the Literally! With Rob Lowe podcast, Kristin clarified that a former boyfriend she’d lent $5,000 to was absolutely not the three-time Emmy-winning actor.

Kristin recalled that when she dated Alec Baldwin, he was already very wealthy. She added that she would have never had to loan him $5,000 if that had been the case, expressing her surprise at the situation.

Kerry Washington, known for her role in Scandal, was featured on the cover of InStyle Weddings in 2005 while engaged to actor Boris Kodjoe. However, the couple ended their engagement in 2007.

Madonna didn’t publicly talk about her relationship with the rapper, who died in 1996 at age 25, until 2015. During an interview with Howard Stern, she mentioned that she was dating Tupac at the time of her memorable and heated 1994 conversation with David Letterman, and explained that he’d really energized her outlook on life.

Before marrying Jim Toth, Reese Witherspoon starred alongside Jake Gyllenhaal in the 2007 thriller Rendition, and they were in a relationship for about two years. This was after her divorce from Ryan Phillippe.

Jake spoke fondly of his ex, saying, “She’s one of the smartest and most resilient people I know—and that goes for most of the women I’ve been close to.”

In her 2025 memoir, My Good Side, the former Vanderpump Rules star shared details about her relationship with the Desperate Housewives actor from the mid-2000s.

She described how they’d often get takeout with his parents at his place. When they had privacy, he’d play guitar and sing to her, often performing ‘Hey There Delilah.’ She said it felt like she was living a dream with someone she’d admired on screen for so long.

Before marrying Livia Giuggioli in 1997 (they later separated in 2019), Colin Firth was in a relationship with Tilly for five years. They have a son, William Joseph Firth, born on September 20, 1990, who is also an actor and appeared alongside his father in Bridget Jones’s Baby.

The U.S. Open tennis champion dated actress Mandy Moore from 2003 to 2004, but their relationship didn’t last.

In a 2018 interview with Howard Stern, Moore revealed that a past relationship had been very painful. She explained that she began dating him at age 18 and that the experience was particularly difficult because they were both so young.

Everyone wonders who inspired Alanis Morissette’s famous 1995 song “Ironic,” and many people think it was the actress from Full House! Morissette said it wasn’t true in a 2021 documentary called Jagged, but many find that hard to believe.

Back in 2005, Reynolds told People magazine that he was a fan of his then-fiancée’s music, joking that it was a little embarrassing when she’d walk in on him listening to it and dancing around in his underwear.

The Canadian band stopped making music in 2007, and when they split up after four years, it was a very amicable separation.

It’s no surprise the actress from Mad Men is attracted to comedians. She dated Jason Sudeikis for a few months in 2010, and later had a short relationship with Will Forte five years later.

The lead actors from Good Will Hunting became a couple in real life, but their relationship didn’t last.

Oh my gosh, when Damon said that on Oprah back in ’98, my heart broke! He was talking about Minnie, and he just… admitted he was single! He said they’d been together, but it wasn’t a romantic thing anymore, just a really strong friendship. He kept saying how much he loved her, how much they cared for each other. It was so sad! He basically said it just wasn’t fate, and if it wasn’t meant to be, there was nothing they could do. I was devastated for them both, honestly. It was like, the perfect couple…but not meant to be!

Driver wasn’t happy with how public the breakup announcement was. She later told the LA Times that she thought it was “fantastically inappropriate” for Matt to reveal they had split on Oprah. She felt it was a poor choice of venue for such a personal announcement.

I remember when Liam Neeson and Helen Mirren first met – it was on the set of Excalibur back in 1981! They actually ended up living together for a while, and Liam has even said Helen gave him his first driving lessons. Sadly, they eventually went their separate ways in the mid-80s, but it was a beautiful romance while it lasted.

In February 2023, Liam Neeson told ET Canada he felt incredibly fortunate to have shared three or four years of his life with her, describing her as truly special.

Finding love in Jurassic Park? What a meat cute.

Jeff Goldblum and his co-star started dating after they finished filming their hit 1993 movie. Goldblum told the Chicago Tribune that he’d been a longtime admirer of hers, saying she was both a talented actress and a wonderful person. He explained he was immediately impressed, but they didn’t realize they had a romantic connection until after the film wrapped.

The couple became engaged in 1995, but their relationship didn’t last, and they broke up two years later. They shared the screen together again for the first time in 2022’s Jurassic World: Dominion, which was the sixth film in the Jurassic World series.

Gillian Anderson, known for The X-Files, dated the creator of The Crown from 2016 to 2020. In 2020, she won an Emmy Award for her portrayal of Margaret Thatcher in the popular Netflix series.

According to Arquette, the two dated while filming their 1995 Western Wild Bill.

During a Reddit question-and-answer session in November 2015, the actor from Clueless confirmed a surprising fact: he and the actress had previously dated. They had both appeared in the 1992 television movie Desperate Choices: To Save My Child.

She was the first actress I ever dated. We were together for a while, even though we lived far apart, and I was really into her.

As a lifestyle insider, I remember when TopMob News first revealed that a Real Housewives of New York star and an actor from Modern Family were dating back in 2015 – it was quite the buzz! Sadly, things didn’t work out, and they went their separate ways by the next year.

The former student of Southland High and the actor known for his role as Theo Huxtable on The Cosby Show were in a relationship for several years before breaking up in 2013.

Before he became famous for starring with John Travolta, the well-known bachelor was already living with Preston in 1987. They shared a pet pig named Max while living together, but their relationship ended in 1989.

Yes, Cher truly believes in finding love again. She and actor Kelly McGillis dated in the 1980s, after Cher’s divorces from Sonny Bono and Gregg Allman.

Before he was Heidi Klum‘s ex, the “Kiss from a Rose” musician romanced a different supermodel.

The pair began dating after they met while filming the 2005 movie Brick, but their relationship only lasted about six months.

The Dawson’s Creek alum and the Josie and the Pussycats star dated for about a year back in 2002.

Reese Witherspoon and the NCIS: LA actor began dating in 1993, shortly after the then-17-year-old Witherspoon relocated to Los Angeles.

Robert Downey Jr., best known as Iron Man, has spoken openly about how his struggles with substance abuse led to the end of his seven-year relationship with Sarah Jessica Parker. In a 2008 interview with Parade magazine, he explained that his drinking and drug use were incompatible with Parker’s lifestyle. He acknowledged she attempted to help him, and expressed regret that he wasn’t able to overcome his issues for her sake.

Matthew Perry, known for Friends and The Hangover, reportedly had a brief romantic encounter in 2003, but it was just a minor, quickly forgotten Hollywood fling.

Kat Dennings, known for her role in 2 Broke Girls, had a short romance with her Thor co-star in 2010. They seemed quite close while promoting the Marvel movie at Comic-Con, but the relationship ended before the film came out the next year.

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2026-02-27 00:25