
In another life, Katy Perry would be Josh Groban’s girl.
I was so thrilled to hear that James Blunt, the guy who sings “You Raise Me Up,” recently got engaged to Natalie McQueen! And honestly, Katy had the funniest reaction – she was playfully over the top about it all.
In a TikTok posted on May 11th, Katy reacted to the news of Josh and Natalie’s engagement – they’d been dating for three years and got engaged in April – by jokingly filling a very large glass with a drink that looked like alcohol.
Katy quickly drank the glass of liquid, spilling some on her bathrobe, while her song “The One That Got Away” played.
She congratulated the couple with a champagne emoji in her TikTok caption. However, the playful post surprised some of her followers. One user commented, “Katy, this is wild!” and another asked, “Are you doing okay?”
To those who don’t know, it might seem like the singer of “One of the Boys” is still heartbroken over a man she dated briefly in 2009.
Despite their brief romantic involvement, she and Josh have stayed good friends. More recently, she dated Canadian Prime Minister Justin Trudeau after ending her relationship with Orlando Bloom.
However, in 2017, Katy admitted on a livestream that Josh was the inspiration behind her 2010 song “The One That Got Away.” She actually called him “the one that got away” during the broadcast.
But for Josh, the news came as a surprise.
The Tony Award nominee admitted being completely surprised when she heard the comment. She described her reaction as a double take, even causing her to spit out her coffee! She added that it was very kind of the person to say it.
You know, I was listening to this song, and it got me thinking. The lyrics paint this picture of a pretty specific type of person – someone with a bit of an edge, maybe a classic car, definitely some ink. And honestly? I realized I don’t quite fit that mold! I was laughing to myself thinking, ‘No Mustangs in my garage, and my skin is tattoo-free!’ It just made me wonder if the songwriter had someone else in mind entirely.

Josh said he was really flattered by the comment, adding that he and Katy have remained close friends and that she’s “the best.”
As for why his and Katy’s didn’t end in fireworks, Josh said they simply weren’t meant to be.
We both valued our privacy,” she explained, “and we came to the conclusion that we worked better as friends.
For more celebrities you forgot dated, read on.

Despite playing tragic lovers in two films—1990’s Too Young to Die? and 1993’s Kalifornia—the actors actually enjoyed a warm and positive relationship with each other off-screen.
Brad Pitt revealed in a 1995 interview with Vanity Fair that he still held affection for Juliette Lewis, his date to the 1992 Oscars where she was nominated for her role in Cape Fear. He described her as a genuinely talented person and fondly remembered their relationship as one of the best he’d experienced. However, he also admitted that the idea that love always solves everything is unrealistic.

It wasn’t just a nostalgic fantasy – Matt Damon and Jennifer Affleck (later Garner) really were a couple at the end of the 1990s. The story goes that Gwyneth Paltrow set them up, as she was famously dating Ben Affleck, Damon’s close friend. They broke up in 2000.
In a 2004 interview with Playboy, Damon described Ryder as a “great woman.” Ryder, in turn, told Black Book in 2009 that Matt was “a really nice guy” and she felt lucky they remained on good terms.

Cameron Diaz and Justin Timberlake had a noticeable connection when they presented together at the 2003 Kids’ Choice Awards. They dated for nearly four years and were serious enough to release a public statement when they broke up in 2007, saying they ended things amicably and remained friends with continued love and respect for each other.

While self-love is the most important relationship, actress Kristin Davis, known for her role in Sex and the City, 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—who she’d lent $5,000 to before their breakup—was absolutely not the three-time Emmy winner people were speculating about.
Kristin recalled that when she dated Alec Baldwin, he was already very wealthy. She jokingly added that she would have never had to loan him $5,000 if that had been the case.

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 explained that when she appeared on David Letterman’s show in 1994, she was dating Tupac and he’d been influencing her perspective on everything.

Before marrying Jim Toth, Reese Witherspoon starred alongside Jake Gyllenhaal in the 2007 thriller Rendition, and the two dated for about two years following her divorce from Ryan Phillippe.
Jake spoke fondly of his ex, saying, ‘She’s one of the most intelligent and resilient people I know – and that’s true of many 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.
Looking back, some of my happiest memories with him were those cozy nights in. We’d often have dinner with his parents at his place, and then, when we had a moment to ourselves, he’d pick up his guitar and sing to me – ‘Hey There Delilah’ was a favorite! Honestly, it felt surreal, like I was living out a dream with someone I’d admired on screen for so long. It was like a real-life fairytale.

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 followed his father into acting and even appeared alongside him 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.
Looking back, it was a really formative experience for me. I started dating him when I was just 18, and honestly, it was my first real heartbreak. It was tough, because we were both so young and figuring things out, but it definitely left a mark. I shared this with Howard Stern a few years ago, and it still feels relevant to how I view relationships now.

It’s a long-standing question in music: who inspired Alanis Morissette’s famous 1995 song “Ironic”? Many believe it was the star of Full House, and despite Morissette’s denial in the 2021 documentary Jagged, it’s hard to believe that isn’t the case.

In 2005, Reynolds told People magazine that he was a big 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 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 comedic actors. She dated Jason Sudeikis for a few months in 2010, and then briefly dated Will Forte five years later.

The actors who played the leads in Good Will Hunting became a couple in real life, but their relationship didn’t last.
In January 1998, Damon appeared on The Oprah Winfrey Show and discussed his relationship status. He explained that he and Minnie had previously been together, but were now just close friends. He expressed deep affection and care for her, stating that while they had a strong connection, their relationship simply wasn’t destined to last. He accepted that sometimes, things just don’t work out.
Honestly, when Matt decided to share the news of our breakup on Oprah, I was pretty shocked. As I told the LA Times shortly after, while I understand wanting to get the word out, that just didn’t feel like the right way to handle something so personal. It felt incredibly inappropriate, and a very public way to end things, which really wasn’t my preference.

Liam Neeson and Helen Mirren first met while filming the 1981 movie Excalibur. They later became a couple—Neeson recalls Mirren teaching him how to drive—but eventually split up in the mid-1980s.
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 a truly special person.

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 he’d been a long-time 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 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 movie 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 Q&A in November 2015, the actor from Clueless surprisingly confirmed that he and the actress had once dated. They had previously appeared together in the 1992 TV movie Desperate Choices: To Save My Child.
Oh my gosh, she was my very first girlfriend, an actress no less! It was tough, though – we were miles apart for so long. I was completely, utterly obsessed with her, totally head over heels.

TopMob News was the first to report that a star from The Real Housewives of New York and an actor from Modern Family were dating back in 2015. However, they broke up the next year.

The former student of Southland High and the actor known for playing Theo Huxtable on The Cosby Show were a couple for several years, but they broke up in 2013.

Before he became a household name, John Travolta was reportedly living with a boyfriend named Preston back in 1987. They shared a home and even a pet pig named Max, but their relationship ended in 1989.

Yes, Cher truly believes in finding love again. She and actor Kelly McGillis dated in the 1980s, after her 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 couple allegedly began dating after they met while filming the 2005 movie Brick, but their relationship only lasted for six months.

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

Oh my gosh, can you believe Reese Witherspoon and LL Cool J dated?! I just found out! It was way back in ’93, when Reese was just 17 and first moved to LA. Seriously, LL Cool J and Reese? It’s amazing! I’m obsessed with finding out everything about this now!

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.

Okay, so the buzz is that Matthew Perry and Mike Tyson had a brief romance back in 2003. Honestly, it was a very short-lived thing – just a quick Hollywood fling that didn’t really go anywhere. It was more of a moment than a relationship, if you know what I mean!

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 didn’t last and ended before the film was released the next year.
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2026-05-12 15:18