17 Throwback Celebrity Couple Photos So Good You Won't Be Able to Look Away

Take a look back at some of your favorite ex-couples and some you had no idea were even together
By Diane J. Cho
March 14, 2019 02:03 PM

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Busy Philipps & Colin Hanks

Credit: Busy Philipps/Instagram

The actors dated in college when they were both students at Loyola Marymount University in the '90s and have since become friends.

“He was my college boyfriend!” Philipps said on Live with Kelly. “We met when I was 18 and Colin was 19… We are very very close friends now — his wife and I are tight, he and my husband hang out. We go on vacation together. He’s real excited that I’m here.”

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Ashton Kutcher & January Jones

Credit: Ron Galella, Ltd./WireImage

The now famous and successful actress dated Kutcher back when she first arrived in L.A. to make a name for herself. Kutcher doubted that his then-girlfriend would make it in Hollywood and boy, was he wrong.

“[He] was not supportive of my acting,” Jones told GQ. “He was like, I don’t think you’re going to be good at this. So – f— you! He only has nice things to say now – if anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated.”

3 of 17

Kelly Preston & George Clooney

Credit: Barry King/WireImage

Way before John Travolta and Amal Clooney were in the picture, the ex-couple dated for two years and even lived together until they broke up in 1989.

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4 of 17

David Gallagher & Megan Fox

Credit: Jim Spellman/WireImage

Once upon a time, these two teenage heartthrobs dated from 2003 to 2004 before going their separate ways. Is it safe to assume the teeny bopper in all of us is still mourning this relationship? We think yes.

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Michael Keaton & Courteney Cox

Credit: Getty

The former Batman and Friends stars were in a serious relationship for five years until they split in 1995.

"It’s the most important relationship I’ve ever had," Cox told PEOPLE right after their breakup in the 90s, "and I think he’s the most wonderful person I’ve ever met.”

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Ryan Phillippe & Reese Witherspoon

Credit: Victor Malafronte/Getty

The stars of Cruel Intentions took their on-screen romance off-screen and the two got engaged only a year after they met, in 1997 at Witherspoon's 21st birthday party. They got married in 1999 while the actress was six months pregnant with their daughter Ava, but announced their separation in 2006.

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7 of 17

Bruce Willis & Demi Moore

Credit: Ron Galella/WireImage

The ex-couple fell for each other hard and fast. In 1987, the two got married in Vegas only four months after they first met. During their up-and-down 11-year marriage, Willis and Moore welcomed three daughters, Rumer, Scout and Tallulah, but sadly called it quits in 1998.

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Ryan Gosling & Sandra Bullock

Credit: Getty

The two quietly started dating while filming Murder by Numbers back in 2002. Their 16-year age difference made headlines but that didn't stop the actors from dating for more than a year before splitting in 2003.

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Miley Cyrus & Nick Jonas

Credit: Kevin Mazur/WireImage

It was love at first sight for the two former child stars.

"We became boyfriend and girlfriend the day we met," Cyrus told Seventeen back in 2008. "He was on a quest to meet me, and he was like, ‘I think you’re beautiful and I really like you.’ And I was like, ‘Oh, my gosh, I like you so much.'"

The sweet romance ended after about a year and now they're all grown up. Cyrus is married to Liam Hemsworth and Jonas is married to Priyanka Chopra.

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Mila Kunis & Macaulay Culkin

Credit: Dimitrios Kambouris/WireImage

The actors dated from 2002 to 2011 and pretty much kept their relationship private from the public eye throughout its entirety. Then, almost a decade later, Kunis spoke about the couple's split on Dax Shepard's podcast, saying it was, "a horrible, horrible breakup. I f—— up."

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Kevin Federline & Britney Spears

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The two had a Chaotic two-and-a-half year marriage that resulted in their own reality series with the same name. They got quickly engaged, closely after Spears' 55-hour marriage to childhood friend Jason Alexander, and threw a surprise wedding in 2004. After a very messy marriage and a tough divorce, the two continue to battle over child support for their sons Sean Preston and Jayden James.

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Cody Simpson & Gigi Hadid

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The singer and model dated for two years but after announcing their split in 2015, Simpson revealed that the decision was mutual.

"Cody and Gigi want each other to be in a place right now that allows him to only focus on his music, fans, and new message, while she can focus and continue building her career," Hadid’s rep told PEOPLE right after the breakup. "They remain friends with no hard feelings and each other’s biggest supporters."

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13 of 17

Zooey Deschanel & Jason Schwartzman

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Schwartzman was Deschanel's first "real" boyfriend, according to Bustle. The two dated when they were both 19.

Now, Schwartzman is married to fashion designer Brady Cunningham and Deschanel is married to and just had her second child with film producer Jacob Penchenik.

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Gwyneth Paltrow & Brad Pitt

Credit: Kevin Mazur Archive/WireImage

Paltrow and Pitt, the 90s "it" couple, dated for two years before they broke up in 1997. Both have since moved on but Paltrow opened up about how she was glad they dated when they did.

“I remember when Brad Pitt and I broke up, it was on the cover of the New York Post and there was no one outside my house,” she told WSJ Magazine. “That would never happen today.”

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Lenny Kravitz & Nicole Kidman

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Kidman revealed that she was once engaged to her Big Little Lies costar Zoë Kravitz's father, Lenny Kravitz. The engagement took place after her divorce from Tom Cruise and before her marriage to current husband Keith Urban. The actress told Vanity Fair that the secret engagement "just wasn't right" and that they were both not ready to take the next step.

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Jenna Dewan & Justin Timberlake

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The two briefly dated while Dewan was backup dancing for the singer. They were friends first, then decided to date shortly after his breakup with Britney Spears but it didn't last very long.

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Jake Gyllenhaal & Kirsten Dunst

Credit: Jeff Vespa/WireImage

The actors were first introduced by Gyllenhaal's sister, Maggie, and began dating in 2002. They eventually moved in together and even adopted a German Shepherd mix puppy before splitting two years later.

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By Diane J. Cho