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