15 Unexpected Celebrity Hookups That Made Us Do a Double Take

Imani Bashir | Sep 21, 2018 Celebrities
15 Unexpected Celebrity Hookups That Made Us Do a Double Take
Image: Frank Micelotta/ImageDirect/Getty Images

Janet Jackson and Matthew McConaughey
Frank Micelotta/ImageDirect/Getty Images

Relationship culture in the celebrity realm is like taking a stroll back to our college days: It's less like wanting to know who's boo'ed up and more like the walk of shame on the late night ... in the middle of campus. There was a time where it wasn't easy to spot these connections ("hookups" as the young folks like to call it) -- like that time Tupac and Madonna maybe got caught creeping. And did M.J. (Michael Jackson) ever fully cop to who "Billie Jean" really was? Nowadays, people can find a whole thread on Twitter to guess who KiKi is and if she really does love Drake. (Yea, thought it was just a song, huh?) It's safe to say that social media can help play a role in finding out who's trolling with heart eyes and why, but it also gives a glimpse into who's double-tapping ... if you know what we mean (*wink*).

Even when the general population is wrong about a hookup, there's one happening somewhere that's bound to make mouths drop once it becomes public knowledge. Celebrities often end up giving us Urkel's "Did I do that?" excuse after stuff goes down -- especially since fans, followers, and TMZ like to find skeletons in closets and dig for the bones buried deep in stars' yards. (Heaven knows the Kardashian-Jenner clan has a target on them as they stay in the spotlight.)

Face it: Folks are nosy and are very (very) curious when it comes to their fave stars and who's messing around with who.

Here's a look at some of the most unexpected celebrity hookups that will really tilt the head and squint the eyes, because we never saw them coming. (Pause.) From Mel B and Zac Efron, to Kim K and Nick Cannon, this list definitely spiced up someone's life -- or maybe added a little salt to it!

  • Mel B & Zac Efron

    Mel B. & Zac Efron
    Jen Lowery/Splash News; Splash News

    Former Spice Girls singer, Mel B, allegedly hooked up with Zac Efron after her split from her husband in 2017. The two met on a dating app, which Efron seems to be no stranger to. He once said he had a Tinder profile, but was unsuccessful due to people not believing it was his real page.

  • Ashton Kutcher & Rihanna

    Rihanna & Ashton Kutcher
    Splash News; Splash News

    Back in 2012, Rihanna was seen heading to visit Ashton Kutcher late at night. Apparently, she told a friend that she thought he was cute and funny, which had them sneaking off a time or two. Outlets even went on to report the pair had an "eight-week fling," so it looks like this wasn't a ha-ha moment for Punk'd.

  • Chelsea Handler & 50 Cent

    Chelsea Handler & 50 Cent
    Splash News; Splash News

    Back in 2010, comedian Chelsea Handler told Oprah Winfrey that 50 Cent was a "sweetheart" and "so cute" -- seemingly confirming their relationship -- while being quick to add that their romance "wasn't the most serious." She did, however, give juicier details in a Howard Stern interview, admitting the couple did hook up and took vacays together.

  • Lenny Kravitz & Nicole Kidman

    Nicole Kidman & Lenny Kravitz
    Splash News; Splash News

    To see this next one coming, is to have vision beyond 20/20. Nicole Kidman spilled the beans about having already had a relationship with Lenny Kravitz's daughter, Zoe, prior to working with her on HBO's Pretty Little Liars.

    But, wait, there's more!

    Lenny and Nicole used to be engaged. Who knew?

  • Pink & Joey Fatone

    Pink & Joey Fatone
    Splash News; FameFlynet.uk.com/Splash News

    Back in 2013, Pink revealed to Glamour magazine, that at one point, she dated NSYNC group member, Joey Fatone. She said Joey was a sweet guy and get this -- he even asked her father to take her out on a date.

    Talk about a true gentlemen  ... Guess nice guys do finish last, though!

  • Janet Jackson & Matthew McConaughey

    Janet Jackson & Matthew McConaughey
    Janet Mayer/Splash News; Splash News

    Miss Jackson admitted that prior to her long-term relationship with music producer Jermaine Dupri, she had a "fling" with our favorite country boy, Matthew McConaughey. This one came out of left field, but Janet Jackson has always kept us in quite a suspense with past lovers. Recently, it was revealed in the Bobby Brown biopic, that she also had a fling with the former New Edition member.

  • Paris Hilton & Val Kilmer

    Paris Hilton & Val Kilmer
    Bauer-Griffin/Splash News; Splash News

    Talk about the most random two people to throw together! Pictures of Paris Hilton and Val Kilmer sucking face surfaced back in 2002 while he was filming the movie Wonderland. Talk about irony for the movie name and this particular pair.

  • LeAnn Rimes & Tiger Woods

    LeAnn Rimes & Tiger Woods
    Splash News; @ParisaMichelle/Splash News

    Golf star Tiger Woods is no stranger to his love for blondes. However, when he started dating LeAnn Rimes many moons ago, the country star's father reportedly protested due to their seven year age difference. Apparently, he was really into LeAnn, that makes us wonder if that would've affected things with Eddie Cibrian down the road.

  • Kim Kardashian & Nick Cannon

    Kim Kardashian & Nick Cannon
    Phil McCarten/REUTERS

    Yes, Wildin' Out creator Nick Cannon dated Kim Kardashian -- just after Ray J, but way before Kanye gave her the "West" last name. The two had gotten cozy with each other up until the sex tape seen 'round the world. (The two eventually split after that.)

  • Sharon Osbourne & Jay Leno

    Jay Leno & Sharon Osbourne
    SPW/Splash News; Splash News

    Is the popcorn getting good? Sharon Osbourne admitted to having a quick "situationship" with Jay Leno, prior to meeting Ozzy Osbourne. She talked about the fling on The Howard Stern Show, stating that Jay just didn't have the stamina.


  • Carmen Electra & Simon Cowell

    Carmen Electra & Simon Cowell
    Splash News; PALACE LEE/Splash News

    Carmen has never been one to shy away from keeping us gasping at her choices of guys (*cough* Dennis Rodman *cough*)... One odd fling was with none other than TV talent show producer Simon Cowell. According to Daily Mail, Carmen and Simon's fling ended when Electra suspected Cowell of foul play with his best friend's wife -- which ended up being true since Simon and the best friend's wife had a child together.

  • Cameron Diaz & Tyrese

    Cameron Diaz & Tyrese
    Splash News; Splash News

    Back in 2007, the Fast and Furious actor Tyrese and Cameron Diaz were spotted at a pre-Oscars party and later lip locked in a Los Angeles nightclub. And just as fast as things got hot and steamy is similarly as quick as the fire went out.

  • French Montana & Khloe Kardashian

    French Montana & Khloe Kardashian
    FameFlynet.uk.com/Splash News

    The Kardashian clan members are no strangers to testing the waters -- including with rappers and ball players. Khloe Kardashian began dating rapper French Montana while he was still legally married to his ex-wife, Deen Karbouch. Khloe and French dated just after her break up with former LA Lakers player Lamar Odom, just before dating Houston Rockets star, James Harden.

    French is clearly in the wrong profession.

  • Heidi Klum & Anthony Kiedis

    Heidi Klum & Anthony Kiedis
    Splash News; Splash News

    Red Hot Chili Peppers lead man Anthony Kiedis admitted to having a fling with international supermodel Heidi Klum. He confessed that he was a bit selfish during their time together and she had just gotten out of a broken marriage to Ric Pipino -- so it wasn't long-lasting.

  • Drew Barrymore & Tom Green

    Drew Barrymore & Tom Green
    Rose Prouser/File Photo BK/REUTERS

    Who would've ever put Drew Barrymore and Tom Green in a room, let alone, together? This match made-for-reality-TV couple were an item long enough to blink and miss it. They even got married before divorcing nine months after saying "I do."

hooking up celebs

More Slideshows