20 Oddest and Weirdest Celebrity Couples of All Time

Justin Timberlake and Fergie

It’s undeniable that most of us have previous relationships that we’d probably like to forget. Whatever the reasons, we’ll tell you that we’re happy to put it where it is: in the past. Even though we always come across perfect couples and in most cases read about perfect celebrity relationships, most of these celebrities have relationship skeletons in their closets that they wish we wouldn’t know about. Whether it’s about a September-January affair that didn’t work out or a partner who couldn’t simply get his act together and stay sober or faithful, relationship skeleton is one area that the rich and famous are unquestionably just like us. That said, 2016 was a tough year for celebrity couples. From the Brangelina breakup that caught everyone off-guard to the very messy divorce between Johnny Depp and Amber Heard, it was somehow a wild and rough ride for many celebrity couples. Despite all these, it’s no secret that we still love celebrity couples and we hope that they have a better 2017. That’s because whenever celebrities are dating or are in a stable relationship, we ordinary people always love it and follow their lives with a little envy.

However, there are times when certain celebrity couples get has thinking like: this is not going to work! This is at the backdrop of the fact that they often seem like they aren’t the perfect fit for one another. No matter the strength of their relationship whirlwinds or how much they publicly confess their love for one another, most of these celebrity pairings always look odd. These celeb pairings are sometimes very odd that even the public has a feeling from the very start that they’re not meant to be. But because we aren’t that judgmental, we suppose you shouldn’t take our word for it. That’s why we’ve compiled this interesting list of celebrity odd relationships that had us breathing a sigh of relief when they came to an end. That’s in addition to one or two relationships which are still going strong even though we can’t actually comprehend how they’re making it work. Enjoy reading through it, see what we mean and have your say.

Before Justin Timberlake and Fergie started collaborated on hits such as ‘Where is the Love?’ the pair had a little thing of their own cooking in the love pot. That was back in 1998 when the then 23-year-old Fergie was still known as Stacy Ferguson of girl group, Wild Orchid. On the other hand, JT was a fresh 16-year-old singer and the younger member of NSYNC.

Robbie Williams and Cameron Diaz

Fergie admitted that the unlikely relationship wasn’t that serious: “It was neither long-term nor that serious. He was 16 and I was 23 and that was before he really got heavy with Britney.” Okay, we get it. Even the pair knew it wasn’t going anywhere because it was downright odd.

Finding celebrities that date, break up and remain friends isn’t easy. That’s why Robbie Williams and Cameron Diaz appear on this list. The British pop-singer met Hollywood actress in the summer of 2003. The couple was soon seen kissing and holding hands on a beach, but the romance didn’t last.

Jennifer Aniston and Adam Duritz

Despite breaking up and moving on, the stars remain strangely close. In fact, it was Cameron who saved Williams’ marriage to actress Ayda Field when the pair was going through tough times. Cameron convinced Williams to give his marriage a second chance and that’s exactly what he did to save the marriage. Ayda was so grateful to Cameron and believes that the Bad Teacher actress could make a great celebrity relationship guru should she consider changing careers.

Jennifer Aniston has the ultimate man in Justin Theroux. The recently married couple looks so loved up that you’d wonder if they have any skeletons in their closets. Wait… did you know that the American sweetheart once dated Counting Crows frontman Adam Duritz?

Macaulay Culkin and Mila Kunis

Well, before her nonsense with Brad Pitt, Aniston had a very brief but hot relationship with Adam. While Adam admitted that they “never slept together,” it was still weird that the rock star went out with Aniston’s Friends co-star Courtney Cox immediately after calling it quits. Whether Adam and Aniston slept together or not, it must have still felt strange on set after Adam jumped from Aniston to Cox.

It’s somehow difficult to think of Mila Kunis without ever thinking about Ashton Kutcher by her side. While the married couple and share two beautiful children, many people aren’t aware that the Ukraine-born actress was in a stable relationship with someone else for almost a decade before she crossed Kutcher’s path. Kunis dated Macaulay Culkin for close to 8 years before calling it quits in 2011 just right in time to meet Kutcher, who was also on the verge of ending his relationship with Demi Moore.

Mariah Carey and Nick Cannon

It’s alleged that Kunis and Macaulay almost walked down the aisle if not for the fact that Kunis wasn’t ready to settle down and start a family. This reason at least makes some sense. And so let’s forget, for a moment, that time when Kunis revealed that the reason why she didn’t marry Culkin was that he was so huge and one couldn’t walk down the street with him!

Mariah Carey is very special in most areas of her life, but her involvement and marriage with bad boy Nick Cannon was a mistake, largely on her part. The beautiful diva is widely considered eccentric especially when it comes to her romantic life, and that was well-evident in her odd relationship with the father of his two beautiful kids. Carey and Cannon dated for little over six weeks (that’s a month and a half) before getting married in 2008. She was 39 at the time and he was 27, but that didn’t bother them.

Two years later, the couple was blessed with two beautiful twins, Moroccan and Monroe. Come 2014, the blissfully “happy” marriage hit the rocks after Cannon started yapping about their intimate moments and even admitted that they were living apart. When it came to divorce settlement, the estranged stars argued back and forth as Mariah felt that Cannon demanded way much than he actually deserved. While being crazy in love, Mariah had trusted Cannon with almost everything in her life, but she felt really betrayed when he turned out to be almost the same like every other man she’d dated.