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20 Forgotten Celebrity Couples That Were Awkward AF

High Life
20 Forgotten Celebrity Couples That Were Awkward AF


The glittering world of celebrity becomes even more interesting when stars become romantically involved. Over the years, we have seen celebrity pairings that have lasted the decades against all odds, like Goldie Hawn and Kurt Russell, Will Smith and Jada Pinkett-Smith, Brad Pitt and – never mind. Power couples of the entertainment world continue to captivate public interest, and garner enormous amounts of public attention.

Let’s face it, we like to know as much about the private lives of celebrities as we possibly can – and relationships are a huge part of that. You may think that due to the intrusive nature of media, you know everything there is to know about your favorite movie star. Think again. Although you may know who their current spouse is, or even their ex-partner, you might be surprised to find out who else they’ve been connected to in the past. After all, everyone has skeletons in their closet. Hollywood’s finest are no different.

From brief liaisons to years long committed relationships, some of these celebrity couples were far too weird and awkward to ever work out. Despite their best intentions, the fates intervened – and it’s a good job, too.

Let’s take a look at 20 Forgotten Celebrity Couples That Were Awkward AF.



Back in 2010, the world was saying goodbye to one of the biggest TV shows ever seen, Lost. While that was happening, Joe Jonas and Demi Lovato were a couple. The pair dated for a brief stint after meeting three years prior on the set of the teen movie Camp Rock. The pair split amicably and have remained close friends, helping each other through various heartbreaks, such as Jonas’s split from model Gigi Hadid in 2015. Lovato dated That ’70s Show star Wilmer Valderrama in 2010. When they split in 2016, the rumor mill started turning and it was speculated that Lovato and Jonas were dating again. Unfortunately, they weren’t.



I know you’re thinking it, so I’ll say it. Is there anyone that Taylor Swift hasn’t been linked to? The two met in true celebrity fashion, on the set of the movie Valentine’s Day. Like most of Swift’s relationships, it lasted a hot minute before being resigned to a song where its memory will be forever immortalized. In a Facebook live interview in 2016, Glee star Lea Michele teased Lautner about his fling with Swift, where he admitted the song ‘Back to December’ from Swift’s 2011 album is about him. In the song, she croons ‘You gave me roses / and I let them there to die.’ Ouch, I’m guessing that wasn’t a pretty break up.



WTF. This one came completely out of left field. The year that *NSYNC graced us all with the gift of their debut album, Justin Timberlake was dating Fergie, before she had joined the Black Eyed Peas. What’s really shocking is the age difference. Fergie confessed the relationship in an interview with Australian magazine, Courier Mail, saying ‘He was 16 and I was 23, It’s before he got real heavy with Britney.’ Pick your jaw up off the floor. Thank goodness it ended, so it could pave the way for the ultimate pop couple we all worshipped – and the break up that give us “Cry Me A River” and its video.



Ah, the young love of Disney starlets. Miley Cyrus and Nick Jonas managed to hold their teen romance together for around two years before they broke up in 2007. Although the pair kept the relationship very private and never confirmed it at the time, Miley fessed up to a US magazine post break-up in 2008. ‘For two years he was basically my 24/7. But it was really hard to keep it from people. We were arguing a lot and it really wasn’t fun.’ Miley recovered from heartbreak and went on to couple up with Aussie actor Liam Hemsworth, who she confirmed her engagement to in October 2016.



The pop-punk princess and the son of Caitlyn Jenner dated for two years, following Lavigne’s divorce from Derek Wibley, lead singer of the band Sum 41 in 2010. Jenner came to prominence on the MTV reality show The Hills as the beau of main cast member Lauren Conrad. A lot of people speculated that Jenner was too clean cut for Avril, but insiders claim that it was her eagerness to wed (and Jenner’s aversion to it) that split them apart. This pairing often gets forgotten in the shadow of Lavigne’s much more public relationship with Nickelback front man Chad Kroeger, who she had a whirlwind romance with before marrying in 2013. They separated after just two short years together in 2015.



Glee co-stars Lea Michele and Matthew Morrison set the rumor mill on fire with speculation of a previous relationship. Both copiously denied it at the time, however in her 2014 book, Brunette Ambition, Michele spilled the beans. ‘I had worked on Broadway with Jenna Ushkowitz and Matthew Morrison before. Matt had been a friend of mine for years, and in fact we’d actually dated back in the day for a Broadway beat.’ As Morrison plays Michele’s teacher and role model in Glee, a lot of people found this a very awkward coupling. It’s called acting people! Of course, Michele went on to have a serious relationship with co-star Cory Monteith from 2011 to his tragic death in 2013.



Grungy rocker of Good Charlotte fame, Joel Madden, faced a barrage of abuse when he began dating squeaky clean Disney starlet Hilary Duff. Not only did fans think Duff was tarnishing her reputation and putting her career on the line, she was only 16 and Madden was 25. Not totally legal. Despite the controversy, the pair kept together for almost two years. Madden went on to marry Nicole Richie with whom he has two children. Duff married athlete Mike Comrie and had one son, Luca. The couple unfortunately filed for divorce in 2014. Looks like someone is still chasing their Cinderella Story.



The Vampire Diaries star Paul Wesley and his co-star Torrey DeVitto dated after meeting on the set of the 2008 film Killer Movie. The couple were together for three years before tying the knot in New York City with a low-key ceremony in 2011. The marriage didn’t work out and lasted a couple of years, before they filed for divorce in 2013. Not many remember the relationship even happened, despite the 6-year duration. Wesley didn’t hang around and began dating another fellow cast mate, Phoebe Tonkin the same year. They were together for four years before splitting in March this year.



Let’s throw it back a couple of decades to look at this truly bizarre pairing. Mission Impossible actor Tom Cruise and diva Cher enjoyed a brief fling together that left us with some memorable pictures. Although the entire thing was over in a blink of an eye, Cher was quick to sing Tom’s praises on a 2013 episode of Watch What Happens Live with Bravo’s Andy Cohen. When Cohen asked Cher about her former conquests, she was quick to respond, ‘I had just the greatest lovers ever,’ before clarifying: ‘Not a long list. It’s just a good list.’ When Cohen pressed her on Cruise, she said he was absolutely in the top 5.



British rocker Chris Martin scooped up Hollywood royalty for a second time after his separation from Gwyneth Paltrow. A-list actress and all round beautiful person, Jennifer Lawrence dated the Coldplay front man on and off for around a year from 2014-2015. The pair tried their best to make things work, but called it quits after Lawrence wanted to move things to the next level. At that point, Martin was still waiting on his divorce confirmation and according to sources, wanted to remain as flexible as possible with his schedule to maximize the time with his children. Prior to this, Lawrence dated Skins star Nicholas Hoult from 2010-2014.



Supermodel and all-round boss babe extraordinaire Tyra Banks dated singer Seal in the mid-nineties, despite being 9 years his junior. The romance was short lived and they made only one public appearance together at an awards ceremony before calling it quits. They made a beautiful couple, but it wasn’t meant to be. Seal went on to wed another model, Heidi Klum. Together, they have four children, including Klum’s daughter Leni whom Seal adopted. Their marriage lasted seven years before they announced their separation in 2012. Tyra has gone one to take over the world, with the immensely popular Next Top Model franchise. She has a son, York, who was delivered via surrogate in 2016.



Did you ever see a more quintessentially 80s couple than Sarah Jessica Parker and Robert Downey Jr? Me neither. It may seem like an alternate universe, but the actors had a seven-year relationship from 1984-1991. Unfortunately, the relationship ended because of Robert’s drug addiction, not because of lack of love. On The Howard Stern Shown on Sirius XM in 2015, Downey told Stern he went to visit Parker to make amends. Speaking about the meeting, he said ‘Seeing her I was like, “She’s so great and so cool and so funny and so in command. I got to meet her kids and I saw the way she and Matthew live and I respect both of them so much.” All’s well that ends well.



Stars of the hit HBO show, Gossip Girl, Penn Badgley and Blake Lively dated for three years after they were both cast in the teen drama. Notoriously private about his relationships, Badgley denied the romance for around a year, before they went public as a couple in 2008. You might think it would be really awkward having to work with your ex, especially when it involves playing their recurring love interest. You’re probably right, but the stars remained close friends with no public shows of animosity. Since leaving the show, Lively has been catapulted to new heights of fame thanks to her movies The Age of Adeline and The Shallows, among others. She also married a fellow Hollywood A-lister, Ryan Reynolds. Badgley married Domino Kirke, sister of Girls star Jemima Kirke, in a small ceremony last year.



Sandra Bullock met TV personality and former CEO of Austin Speed Shop Jesse James when she arranged for her godson to go on a tour of one of his shows. The pair hit it off and married in 2005, however their marital bliss came crashing down in 2010 when numerous women came forward, claiming that James had been unfaithful. Despite issuing a public apology and checking himself into rehab, Bullock filed for divorce from lothario James and the two separated in June of the same year. James went on to have a romance with tattoo artist Kat Von D, which ended a year later in pretty much the same way. Bullock remains a jewel in Hollywood’s crown and happily adopted a son as a single parent. You go girl.



Perhaps one of the weirdest couplings ever, Jackass star and British TV personality Stacey Solomon dated for six months after meeting on the set of the celebrity ski competition show, The Jump. Known for her childlike persona and excitable attitude, many fans were shocked to see Solomon date crazy stuntman and all round wild child, Steve-O. Despite being openly smitten with each other at first, it was widely reported that the relationship broke down due to distance. Steve-O didn’t hang around and went on to have an on-off relationship with Kat Von D. At the time of the split, Solomon’s representative said, ‘I can confirm Stacey and Steve-O are no longer together. Stacey is really hurt by the whole situation, and it’s not something she feels able to talk about at this moment in time.’ D’aw.



Dance superstar and wife of Channing Tatum, Jenna Dewan, used to be a back-up dancer for Justin Timberlake. The two briefly dated after Timberlake’s highly publicized relationship with Britney Spears came to an end. Dewan was grilled on the romance in May 2017 by Andy Cohen on Watch What Happens Live. ‘We were like friends that then dated,’ she said. ‘No, I was not the rebound! I was very clear, not to be [a rebound]. He’s sexy, of course he’s sexy. But no, I was not a rebound. We’re still friends. It’s not as salacious as everyone thinks.’ Thankfully it ended almost as soon as it started to pave the way for Jessica Biel and JT, and Jenna and Channing Tatum. #couplegoals.



Actress Heather Locklear and Motley Crue bad boy Tommy Lee were married for 7 years, from 1986-1999. While it all ended in divorce for this odd couple, Locklear shared a throwback picture of herself and Lee kissing last year, on what would have been their 30th wedding anniversary, with the caption ‘Happy 30 years baby.’ That’s a little awkward. Both parties went on to marry different people – let’s not forget the media storm around Pamela Anderson and Lee’s volatile marriage and those videos. Locklear went on to have a daughter with Bon Jovi guitarist, Richie Sambora. The two divorced in 2006.



After meeting on the set of 2002 crime thriller Murder by Numbers, the pair quickly became an item, despite their almost 20-year age gap. Gosling was just 22 at the time and played a high school student in the movie, while Bullock was 37. The fling lasted around a year, but left behind a plethora of really awkward photos for us to look back on. Bullock went on to marry Jesse James and Gosling went on to have a relationship with his The Place Beyond the Pines co-star Eva Mendes. The couple have two daughters together but have yet to wed. Come on, Ryan.



There’s something very off about this bizarre celebrity pairing. Nick Cannon and Kimmy K had a romance for a few brief months from 2006-2007. In 2012, Cannon confessed that the relationship ended due to Kim lying about the existence of the famous sex tape. Speaking on The Howard Stern Show, he said, ‘This was my issue. We talked about this tape…And she told me there was no tape. If she might have been honest with me I might have tried to hold her down and be like “That was before me” because she is a great girl. She’s actually one of the nicest people you’ll ever meet. But the fact that she lied and told me that there was no tape?’ Cannon went on to marry Mariah Carey, but the couple sadly divorced in 2016. Unless you’ve been living under a rock, you know that Kim is married to moody rapper, Kanye West.



Weird, right? Way back when 3rd Rock From the Sun was still on our TV screens, Ryan Reynolds was busy starring in his own sitcom, Two Guys and a Girl – and dating Kristen Johnson. The unlikely duo shared a string of dates, including attending the premiere of The Green Mile together. It didn’t last long and Reynolds is now happily married to the gorgeous and supremely talented Blake Lively. The couple share two adorable children. Johnson continues to act with spots on hit shows such as Ugly Betty and Modern Family under her belt. It just goes to show that not all celebrity relationships have to end in long, bitter divorces.

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