Love may be blind and beauty is in the eye of the beholder, but sometimes, certain couples get together and you just can’t figure out what drew them to one another in the first place! In the world of Hollywood, celebrities cycle through relationships the way the rest of us change our clothes, which can make for some truly odd pairings.
Beyond physical appearance, these 15 celebrity couples have us wondering how they possibly could have met, since they tend to run in different circles. And, even when they did meet, how did they find enough common ground to maintain a relationship or even a marriage? Opposites can attract, and while some of these couples have since split, with the people involved moving on to other partners who make a lot more sense, others have defied the odds and are still going strong, even if we never imagined they’d be able to stick it out! Finding true love is a rare thing, and if these people managed to find it with someone no one saw coming, then who are we to judge? Sometimes, defying expectations can lead to that fabled happily ever after (and at other times, not so much).
15 Gwen Stefani & Blake Shelton
She’s California cool, and he’s a down home country boy. But for some reason, these two were attracted to one another while both were going through massively difficult times in their personal lives. In the summer of 2015, both Shelton and Stefani announced their separate splits from their long-term partners—Shelton from country singer Miranda Lambert after four years of marriage over rumors of infidelity and opposing future goals for their relationship, and Stefani from Bush frontman Gavin Rossdale, her husband of 13 years and father of her three sons.
No one ever expected these two to hit it off the way they did, owing to the disparity between them. But thanks to mutual heartache, a gig on TV’s The Voice, and an interest in music, this celebrity couple has defied the odds to stay together ever since with their much-publicized romance that has seen them become tabloid staples. Only time will tell if they can stick it out for the long haul!
14 Avril Lavigne & Brody Jenner
You might have forgotten about this truly weird pairing, but the early 2010’s were a crazy time, guys. Beginning in 2010, pop-punk singer and eyeliner aficionado Avril Lavigne got involved with reality star Brody Jenner of The Hills fame, and they actually stuck it out for close to two years! Clearly, Lavigne had a little bit more cache at the time compared to Jenner, who had mostly made a name for himself dating women from reality shows (including Kristin Cavallari and Nicole Richie, to name a couple), and Jenner eventually became tired of living in the singer’s shadow. (He may have also been annoyed with trading in his trademark OC looks to jive better with Lavigne’s style, because how else do you explain that lime green tie?)
After refusing to join Lavigne on her Asia tour, Jenner ended things. Since then, both have found love again, Lavigne with Nickelback frontman Chad Kroeger and Jenner with Kaitlynn Carter.
13 Jennifer Aniston & Justin Theroux
For so long, we were used to seeing Jennifer Aniston with golden boy Brad Pitt until Angelina Jolie came between the two and people started wearing T-shirts declaring their affinity for one woman or the other. Afterwards, Aniston dated a slew of wrong-for-her men, including Vince Vaughn and John Mayer, before she finally settled down with Justin Theroux, which no one saw coming.
Compared to the effortlessly tanned and toned America’s Sweetheart, Theroux was considered a bad boy of sorts, prone to dressing in lots of leather, living the New York life, and not afraid of the occasional nude scene. Once the two got together in 2010 after hitting it off on the set of Wanderlust, they were seen stepping out in matching all-black outfits as Aniston embraced the east coast. Despite rumors that swirled about the pair’s unhappiness, work schedules, and Theroux’s close friendships with other women, the two were engaged in 2012 and married in 2015.
12 Alanis Morissette & Ryan Reynolds
Before Blake Lively and ex-wife Scarlett Johansson, Ryan Reynolds was cozying up to singer Alanis Morissette in a pairing that left a lot of people scratching their heads. Beyond being brunette and Canadian, these two didn’t seem to share that much in common, but it didn’t stop them from getting engaged and sticking it out for an astonishing four and a half years!
We’re used to seeing Morissette in all her angsty glory, thanks to her landmark album, Jagged Little Pill, whereas Reynolds was kind of a goof, but a hot goof, who managed to get shredded enough to become an action hero. While the two got involved on the cusp of Reynold’s fame, they broke up in 2007 and Morissette ended up writing an album that she described as going through the stages of grief that came from the breakup. Now, of course, we know that Reynolds is happily married to blonde goddess Blake Lively, and the couple share an adorable family with their two young daughters!
11 Renée Zellweger & Jack White
If the early 2010’s were a crazy time, then the 2000’s were way, way weirder. So weird that you probably blocked out the fact that Renée Zellweger was not only involved with White Stripes frontman Jack White, but that the two were actually engaged!
We know that White already had a strange dating history, having been married to his bandmate, Meg White, previously, before claiming in other interviews that the two were siblings, and Zellweger would go on to have an odd future in romance as well, including her short-lived and seemingly random marriage to country singer Kenny Chesney in 2005. But, before that, both White and Zellweger dated for about a year and a half before suddenly calling it quits in 2004. The couple had met while filming the movie Cold Mountain, and it seems that their opposite natures are eventually what drove the low-key couple apart. We’re kind of okay with that, however, because these two just didn’t mesh well in our minds!
10 Jennifer Lawrence & Chris Martin
After ending her on-again, off-again romance with Nicholas Hoult, Jennifer Lawrence went on to date some guys that left us wondering what exactly is with her taste in men. Most recently, the Oscar winner has been linked to director Darren Aronofsky, who is 22 years her senior, but her weirder relationship came with Coldplay frontman Chris Martin.
This couple was the subject of much speculation, mostly because it just didn’t seem to make much sense. While Lawrence has a reputation for being an ‘every girl’ who loved pizza and had a habit of tripping on the red carpet, Martin had recently split from wife, Gwyneth Paltrow, famed for her pseudo-scientific lifestyle website GOOP and touter of all things kale. Back in 2014, though, after Paltrow and Martin had “consciously uncoupled,” he struck up a relationship with Lawrence, who is 13 years younger than him. After about a year together, in between which there were multiple breakups, this odd couple ended things for good in August 2015.
9 Cameron Diaz & Benji Madden
Who would have pictured that Benji Madden of Good Charlotte and Cameron Diaz would ever end up together? Not us, that’s for sure! These two look so strange together that they regularly make the lists for odd celebrity couples because no one can quite believe that they’re together and how it even happened in the first place.
Well, it turns out that it pays to have friends in high places because it was actually Nicole Richie–Madden’s twin brother Joel’s wife–who brought these two together back in 2014. With his tattoos and her megawatt smile, this couple leaves people wondering what exactly they have in common. Madden has a history of dating beautiful blondes, while Diaz tends to hook up with her costars, most notably Matt Dillon and Jared Leto. However, despite her long list of ex-lovers, Diaz has said that “no one compares” to husband Madden, whom she married in a secret ceremony in 2015, and so we hope these two crazy kids can keep it going!
8 Aaron Taylor-Johnson & Sam Taylor-Johnson
Age ain’t nothin’ but a number, but while Aaron Taylor-Johnson and wife Sam have been trying for ages to convince naysayers of exactly that, they haven’t quite managed to convince everyone that their love is real, true, and not at all weird.
The couple met back in 2009 when Aaron was just 19 and his now-wife was 42 and directing him in a film. 23 years may separate this pair, but Aaron claims that not only does he not notice it, but that he has always felt like an old soul and prefers to be a family man rather than joining other twenty-somethings on a road to self-destruction. Their romance was a whirlwind one, and by the time he was only 20, the two married and changed their names to include them both! The Taylor-Johnsons had previously been known as Aaron Johnson and Sam Taylor-Wood, but combined them when they wed. They welcomed two daughters in addition to Sam’s two from a previous relationship and seem to be living happily every after despite raising more than a few eyebrows.
7 Macaulay Culkin & Mila Kunis
We’re so used to seeing Mila Kunis with That ‘70s Show co-star and now-husband Ashton Kutcher that it’s easy to forget the Bad Moms star once dated Macaulay Culkin for a staggering eight years! This strange duo met in 2002 and kept things going until 2011 before quietly breaking it off. While she’s been declared a bonafide hottie throughout her career, Culkin had lost some of the lustre that made him a household name as a child star. Enduring personal tragedies and a failed marriage that began when he was 18, Culkin sought some type of stability, which Kunis was happy to provide. The pair even attended Michael Jackson’s funeral together!
However, before they split back in 2009, Kunis wasn’t sure she’d ever get married, even to her long-term boyfriend, saying that marriage wasn’t that important to her. Of course, we know that she’s since changed her tune, having married Kutcher and welcomed two children with him, but this long-time odd couple is still one for the books!
6 Matthew Perry & Lizzy Caplan
You probably had to do a double take for this celebrity couple, but it’s true! Not only did Friends star Matthew Perry and Masters of Sex’s Lizzy Caplan date, but they stuck things out for six whole years! This pair were so low-key you probably didn’t even know that they were a thing, but they actually were, from 2006 to 2012. Rarely photographed together, it was a year and a half before the split was even confirmed, although sources said it was amicable, even considering the ugly reason behind it. Despite their serious relationship, it was said that Caplan wanted some sort of commitment from the actor, who famously battled alcohol and prescription pills while filming the sitcom that made him famous. Perry didn’t want to get married–to Caplan or to anyone, it seemed–and things ended.
True to that relationship, since the split, both actors have kept things pretty quiet in their personal lives, instead making themselves known for their work.
5 Mary-Kate Olsen & Olivier Sarkozy
We know it’s probably not totally fair to use this photo to showcase the relationship between Mary-Kate Olsen and Olivier Sarkozy, but Olsen’s expression in this snap was just too good to pass up!
An odd couple that tends to eschew the Hollywood limelight despite the obvious public interest in their relationship, these two began dating in 2012 and actually waited three years before tying the knot. However, the clock was ticking for Sarkozy, who is 17 years older than his bride, and he wanted to lock things down after only 10 months. Olsen, on the other hand, rejected his initial proposal and waited until 2014 before finally saying yes. Since marrying, the pint-sized star and entrepreneur with a million-dollar empire has become a stepmom to Sarkozy’s two kids from his previous marriage, although we can’t imagine that five-foot-tall Olsen is able to be all that authoritative! While we can’t say or be sure if this couple has enough staying power, we’re certainly interested to watch what unfolds!
4 Tom Cruise & Cher
Can you get more ‘80s than this duo? Tom Cruise was just a young thing when he got involved with Cher in another romance that had people wondering what the eff was going on. Cruise was just starting out when this celebrity couple hooked up in 1987, whereas Cher was enjoying her peak, complete with outlandish Bob Mackie attire. While one would think that the famous Cher would have had the upper hand in this relationship–especially with 16 years on her younger beau–apparently, it was the opposite! Cher has said that she was crazy for the actor and counts him among the top five of all of her lovers!
Easily one of the most random couples to ever happen in Hollywood, this pairing was a brief one, but one that clearly made a lasting impression on both stars as well as the public. However, Cher apparently wished more had happened between the two, saying a “great big romance” might have been possible, were it not for their conflicting schedules. Oh, if only!
3 Evan Rachel Wood & Marilyn Manson
There’s something jarring about seeing these two together, even though it’s been years since they were involved. It was another May-December romance, with Evan Rachel Wood at 18 and shock-rocker Marilyn Manson twice her age at 36, but age was far from the strangest thing about these two. At the time these two got together, Manson was still involved with burlesque star Dita Von Teese, who cited this new couple’s burgeoning relationship as one of the reasons for her breakup with the rock star.
Wood and Manson embarked on an on-again off-again relationship that lasted years and saw the then-teenage Wood appear in one of Manson’s music videos that featured the couple making out under a shower of blood. When asked to comment on her relationship years later, Wood said that she was drawn to the promise of freedom and no judgments offered by Manson and was attracted to his androgynous look (Wood came out as bisexual in 2011). The two got engaged, but split before tying the knot.
2 Padma Lakshmi & Salman Rushdie
We know that Salman Rushdie is an acclaimed author, but looking at photos of him with Padma Lakshmi and you can see that this was a clear case of when beauty got with the beast. The host of Top Chef is undeniably gorgeous, whereas the Pulitzer Prize-winning and controversial writer has what many may generously call an “interesting look.”
Despite the discrepancies in appearance and age (Lakshmi was 28 and Rushdie was 51 when they met), this couple stuck it out for eight years and even got married, but things weren’t entirely blissful. In her memoir, Lakshmi described Rushdie as hopelessly needy and cold when it came to her personal battle with endometriosis (he called her a “bad investment”). In his own memoir, Rushdie snapped back, saying that Lakshmi was narcissistic and moody. Clearly, this couple was attracted to one another despite their differences, but like many volatile relationships, they eventually fizzled out.
1 Naya Rivera & David Spade
What is it about David Spade? The guy isn’t all that good-looking or talented, and yet he has a dating history filled with some of Hollywood’s most beautiful women, including Heather Locklear, Julie Bowen, and Nicollette Sheridan. Most recently, though, Spade has gotten together with Glee actress Naya Rivera, who’s 23 years his junior and way out of his league, if we do say so ourselves!
This unlikely couple was first seen getting cozy in April 2017, but had reportedly already been involved for a few weeks. Since April, they’ve been spotted out at dinner, but multiple people have claimed that the whole thing is casual and just for fun. While they may just be having a good time together, this random pairing of the 53-year-old and the 30-year-old was strange enough for us to put it as number one on our list, and we’ll bet that plenty of people never saw it coming before now–we certainly didn’t!
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