Finding Out These Celebrities Used to Date Will Blow Your Mind

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It’s enjoyable to look at pictures of celebrity couples who are currently together, but discovering which stars used to date each other can be really surprising.

Now that we realize many of you weren’t even alive when the movie stars we admired were first becoming famous – back when we paid eight dollars for theater tickets or four dollars to rent VHS tapes from Blockbuster – let us tell you what things were like back then.

Whether it’s Brad Pitt’s dating life before Gwyneth Paltrow, the couples who were once engaged or lived together (and looked great doing it!), or even exes who remain connected through their children, the world of celebrities is full of past connections. Stars often find each other, even if just for a short time.

Let’s just say, going down that road is a real trip.

Before you completely disconnect for the holidays, take a moment to appreciate a fascinating piece of Hollywood history. It’s a story filled with romance, a touch of sadness, a cool, edgy style, and features many actors who would later win Oscars. These stars, some looking sweetly naive as they entered the spotlight, often coordinated their outfits in subtle ways.

You’re not mistaken – some celebrities appear more than once on this list! Both Ryan Reynolds and Alanis Morissette dated around before and after their relationship in the 1990s, eventually finding long-term partners.

Let’s take a trip down memory lane and rediscover some celebrity couples from before social media tracked every detail of their lives. We’re here to remind you of a time when dating was a little more private.

Despite playing tragic lovers in the films Too Young to Die? (1990) and Kalifornia (1993), the actors actually enjoyed a warm and positive relationship off-screen.

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 received an Oscar nomination 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, despite what many believe.

Okay, let’s talk about a celebrity couple you might remember! It’s true – Matt Damon and Jennifer Garner were a thing back in the late ’90s and early 2000s. The story goes that Gwyneth Paltrow actually set them up – she was dating Ben Affleck, who’s obviously Matt’s close friend. Sadly, they went their separate ways around the year 2000, but it was a pretty memorable romance for that era!

Years later, in a 2004 interview with Playboy, Damon described Ryder as a “wonderful person.” Ryder, in turn, told Black Book in 2009 that Matt was “one of the kindest, nicest guys,” and she felt fortunate they remained friends.

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 their split in 2007 was announced with a formal statement emphasizing their continued friendship, 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 added that because of his financial situation at the time, she wouldn’t have had to lend him $5,000, and expressed her surprise about it.

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 discussed her famously tense 1994 conversation with David Letterman, revealing, “I was dating Tupac back then, and he really got me thinking about everything in 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’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 that occurred in the mid-2000s.

She described how they’d often have dinner with his parents at his home. When they were alone, he would play guitar and sing to her, often performing ‘Hey There Delilah.’ She said it felt like she was living a dream with someone she had admired on screen for years.

Before marrying Livia Giuggioli in 1997 (they later separated in 2019), Colin Firth was in a five-year relationship with Tilly, and they had a son, William Joseph Firth, born on September 20, 1990. William 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 caused her a lot of pain. She explained that she began dating him at the age of 18, and they were both very young at the time.

Everyone wonders who inspired Alanis Morissette’s famous 1995 song, and many people believe it was the star of Full House! Morissette claimed it wasn’t true in the 2021 documentary Jagged, but many find that hard to believe.

Back in 2005, Reynolds told People magazine that he was a big fan of his then-fiancĂ©e’s music, joking that it could be embarrassing when she walked 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 process.

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 briefly dated Will Forte in 2015.

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

Damon shared on The Oprah Winfrey Show in January 1998 that he was currently single. He and Minnie had been in a relationship previously, but they were no longer together romantically. He emphasized that they remained close friends and that he cared for her deeply, stating that while they had a strong connection, their relationship simply wasn’t destined to last.

Driver didn’t appreciate Matt announcing their breakup on Oprah. She later told the LA Times that she thought it was a very inappropriate way to share such personal news, especially given the public nature of the show.

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 separated 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 truly special.

Finding love in Jurassic Park? What a meat cute.

Jeff Goldblum and his co-star started a relationship after working together on a popular 1993 film. Goldblum later told the Chicago Tribune that he had always admired her talent and personality, and they discovered their connection after filming wrapped up.

The couple became engaged in 1995, but their relationship ended after two years. They didn’t share the screen together again until 2022, when they appeared in Jurassic World: Dominion, the sixth film in the Jurassic World series.

Gillian Anderson, known for her role in 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 confirmed a surprising fact: he and the actress had previously dated. They had both appeared in the 1992 TV 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 crazy about her.

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

The former student of Southland High and the actor known for his role as Theo Huxtable on The Cosby Show were together for several years but broke up in 2013.

Before he became a household name, John Travolta was involved with Preston in 1987. They lived together and even shared 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 pair apparently began dating after they met while filming the 2005 movie Brick, but their relationship only lasted half a year.

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

NCIS: LA star and actress Reese Witherspoon began dating in 1993, shortly after Witherspoon moved to Los Angeles at age 17.

Robert Downey Jr., known for playing Iron Man, has spoken openly about how his struggles with drugs and alcohol led to the end of his seven-year relationship with Sarah Jessica Parker. In a 2008 interview with Parade magazine, he explained that his lifestyle was incompatible with Parker’s, and that despite her efforts to help him, he wasn’t able to change. He said she was upset by his inability to get his life on track.

Matthew Perry, known for Friends and The Hangover, reportedly had a brief romantic encounter in 2003, but it was a short-lived fling that didn’t amount to much in the world of Hollywood relationships.

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 came out the next year.

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2025-12-21 11:18