Can You Believe They Dated?

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Can You Believe They Dated?

From Christina Applegate and Brad Pitt to Justin Timberlake and Fergie, see Hollywood's odd couples of the past

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Justin Bieber & Kourtney Kardashian

One of the most surprising pairings in recent Hollywood history may have been Justin Bieber and mom of three Kourtney Kardashian, who were reportedly seeing each other in 2015 following the reality star’s split from ex Scott Disick. “Justin bragged to friends,” a source told Us of their headline-making hookups (Kardashian is 15 years Bieber’s senior.)

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Taylor Swift & Taylor Lautner

Taylor squared! Taylor Swift has dated her fair share of Hollywood’s leading men, and her lyrics have reflected the very public ups and downs of her relationships. In August 2009, she and Twilight werewolf Taylor Lautner became an item, but they split before the end of the year, though they did costar in 2010’s Valentine’s Day. 

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Joe Jonas & Ashley Greene

Joe Jonas opened up about losing his virginity at the age of 20 in a 2013 piece for New York magazine’s Vulture, noting that he learned a lot from Twilight star Ashley Greene, his first serious girlfriend. The pair split in 2011 after two years of dating.

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Miley Cyrus & Nick Jonas

Back in the day, fellow Disney stars Miley Cyrus and Nick Jonas seemed like a match made in sparkly tween heaven. In a 2015 interview with Elle magazine, the heartthrob revealed that the pair just “ran in different circles” as they grew up. The pair broke up in 2007.

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Britney Spears & Colin Farrell

Britney’s got a thing for bad boys! The pop princess and Hollywood’s notorious bad boy Colin Farrell first stepped out together at the 2003 premiere of The Recruit, but Farrell later denied that they were ever anything more than a fling.

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Tom Cruise & Sofia Vergara

Tom Cruise and Sofia Vergara may seem worlds apart nowadays, but the pair went out a few times in 2005. Ultimately, however, the Modern Family Star was reportedly “fundamentally terrified” by Scientology, according to Andrew Morton’s book Tom Cruise: An Authorized Biography

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Chris Evans & Jessica Biel

Before he was Captain America, Chris Evans was an up-and-coming actor dating 7th Heaven actress Jessica Biel back in 2003. The pair called things off after more than two years.

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Mark Salling & Naya Rivera

Glee fans were excited when they learned that on-screen lovers Puck (Mark Salling) and Santana (Naya Rivera) were dating in real life in 2010; the costars were never exclusive, however, which led to a messy breakup and Rivera keying and egging Salling’s Lexus, a source told Us at the time. 

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Bella Thorne & Cody Simpson

Before he was linked to model Gigi Hadid, Australian singer-songwriter Cody Simpson was feeding rumor mills by showing up on red carpets with Disney star Bella Thorne in 2011. The pair — who were 14 and 16 at the time — never confirmed their relationship status, but both have since been romantically linked to other stars since.

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Kylie Jenner & Cody Simpson

Before there was Tyga, Kylie Jenner had her fair share of rumored beaus, including pop singer Cody Simpson, whom she was linked to in 2011. In 2012, Jenner denied that the pair’s relationship was romantic, telling Seventeen that they were just “good friends.”

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Frankie Muniz & Hilary Duff

Malcolm’s got the moves! Frankie Muniz and Hilary Duff co-starred in 2003’s teen action flick Agent Cody Banks, and sparks flew from the get-go. The pair dated for two years before calling it quits in 2004.

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Jake Gyllenhaal & Kirsten Dunst

Jake Gyllenhaal’s first high-profile romance was with none other than Bring It On star Kirsten Dunst, whom he lived with in L.A. (along with their dog Atticus!) while they dated between 2002 to 2004.

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Miley Cyrus & Tyler Posey

Miley Cyrus and Tyler Posey first met on the set of Doc, which also starred Cyrus’ dad Billy Ray, in 2000, when the Teen Wolf star was just nine years old and Cyrus was just seven. “We were so damn young … I would get excited when we would hold hands,” Tyler told ET of their cute pre-teen relationship, adding that the “Wrecking Ball” singer was his first kiss.

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Vanessa Hudgens & Josh Hutcherson

Vanessa Hudgens and Josh Hutcherson were first linked in February 2011, following Hudgens’ very public break-up with High School Musical costar Zac Efron. The pair, who co-starred in Journey 2: The Mysterious Island, denied their relationship in public, but Hutcherson hinted that he was dumped in a 2013 interview with Seventeen. 

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Brenda Song & Trace Cyrus

Disney actress Brenda Song and Metro Station lead singer Trace Cyrus dated on-and-off for five years, and their relationship stood the test of broken engagements, a pregnancy rumor, and short-lived relationships with other people. At present, the couple seems to be weathering the storm of their rocky relationship and is back on.

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Zach Braff & Drew Barrymore

The actress -- who has more recently been spotted with her ex and He's Just Not That Into You costar Justin Long -- was spotted dancing and making out with the Scrubs star in a NYC club in July 2007.

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Justin Timberlake & Fergie

"He was 16 and I was 23," she told Australia's Courier Mail. "It was before he got real heavy with Britney."

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Scarlett Johansson & Josh Hartnett

Distance and differing commitments did this couple -- who dated for more than a year -- in 2007. "At the end of the day we're just ordinary people, and it didn't work," he has said, adding that the breakup was "really painful."

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Diddy & Sienna Miller

Shortly after the birth of his twins in 2007, Diddy was frequently seen partying with the actress, staying out so late one night that he was seen escorting her to her hotel at 9 a.m., where the two reportedly had breakfast. Both denied they were dating.

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Ben Affleck & Famke Janssen

Although the X-Men star denies any dalliance with the actor -- the now-married star is seven years her junior -- and has said they were "just friends," the two were linked in 2001.

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Brooke Shields & Michael Jackson

In 1984, the actress was the late singer's date to the Grammy Awards. He wrote about their romantic involvement in his 1988 autobiography, but Shields claimed they were just friends. "We grew up together," she told the AP. "He trusts me."

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Nicky Hilton & Kevin Connolly

After a two-year romance, the heiress dumped the Entourage star in October 2006 after she suspected he had been unfaithful. Although Hilton started dating him just weeks after she annulled her three-month marriage in late 2004, Connolly said "it was a pretty normal relationship."

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Cher & Tom Cruise

Cher dated Cruise in the mid-'80s. "It was a long, long time ago and neither one of us ever talked about it and I don't know why," the singer told ET. "I loved him though, he was amazing." Cher later romanced Bon Jovi's guitarist in 1990.

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Christina Applegate & Brad Pitt

The Samantha Who? star and the actor were linked in 1988.

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Heather Locklear & Tom Cruise

"I don't think we kissed. It was more friends," Locklear has said of her short-lived 1982 romance with Cruise.

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Aaron Carter & Lindsay Lohan

In 2005, Carter admitted on The Big Idea With Donny Deutsch: "I started dating Hilary [Duff] on my 13th birthday... I was dating her for like a year-and-a-half and then I just got a little bored so I went and I started getting to know Lindsay, dating Lindsay."

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Jennifer Aniston & Adam Duritz

"We never even slept together," the Counting Crows frontman has said of his relationship with the Friends star in 1995. After they split, the rocker dated her BFF and co-star Courteney Cox.

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Nick Lachey & Kristin Cavallari

In March 2006, the Laguna Beach star hung out at the crooner's home with a delivery dinner and videos. "They are talking and texting all the time," a source told Us. But days later he was spotted with current girlfriend Vanessa Minnillo.

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David Arquette & Alyssa Milano

Before the former Who's the Boss? star developed a penchant for baseball pitchers, she was linked to Courteney Cox's hubby in 1991.

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Richie Sambora & Cher

The Bon Jovi lead singer and Cher dated for about a year before splitting in 1990.

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Can You Believe They Dated?

From Christina Applegate and Brad Pitt to Justin Timberlake and Fergie, see Hollywood's odd couples of the past