20 Celebrity Couples You'll Never Guess Dated in Real Life

Opposites attract, but do they last?

Complex Original

Image via Complex Original

Some combinations, like peanut butter and jelly, are made for each other. Others, like oil and water, are not. The same goes for celebrities, who, as the tabloids desperately want to prove to you, are just like us. Sometimes they're attracted to the wrong people. And sometimes, they're attracted to people who seem like their polar opposites, but turn out to be their soul mates instead.

It's hard to say what attracts people to each other, but when the primal instinct kicks in, no one can stop it. Not even the rich and famous. This urge has resulted in a slew of romances that just don't make sense to us or anyone else. To honor life's little surprises, we've gathered some of the quirkiest, strangest, and most unorthodox pairings to bring you 20 Celebrity Couples You'll Never Guess Dated in Real Life.

Written by Valeriya Safronova (@vsaffron)

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Danny Boyle and Rosario Dawson

Dated: August 2012-current

When you give this pair some deep thought, they make sense together. Both are talented, accomplished, and private celebrities. On the surface, however, there are a few suprises, including their 23-year age gap. Staying the the shallow lane, we can't help but notice that Dawson is smoking hot, while Boyle is...sweet-looking. This may be an unexpected match, but something about it is heart-warming.

Billy Corgan and Tila Tequila

Dated: 2009

Things Billy Corgan is famous for: being the front-man of alternative rock band Smashing Pumpkins and living with Courtney Love. Things Tila Tequila is famous for: making a sex tape with two female porn stars, being engaged to heiress Casey Johnson, hosting her own dating show, and probably her most important accomplishment to date, becoming the most popular artist on MySpace. Notice any crossover between these two? No? Neither did they, as it turns out. Their relationship was one and done.

Sandra Bullock and Ryan Gosling

Dated: 2002-2003

Before Sandra Bullock married Jesse James, her ex-husband slash serial cheater slash scumbag extraordinaire, she dated Ryan Gosling, who wasn't exactly the meme-inspiring Gos we know him now. If she only knew.

After meeting of the set of Murder by Numbers over a decade ago, Bullock went public with the ultimate ladykiller, despite being 16 years his senior.

Alanis Morissette and Ryan Reynolds

Dated: 2002-2007

Ryan Reynolds is what is known in some circles as a "serial celebrity husband." Yes, he is well-known in his own right, but not quite to the same extent as the two women he's married, Scarlett Johansson, who is famous enough to be called ScarJo; and Blake Lively, who is so gorgeous that if you don't know who she is, you must never leave your house—or go on the Internet.

Before tying the knot twice, Reynolds was actually engaged to Alanis Morissette, a great looking, talented woman, but not quite the blonde bombshell type that Reynolds seems to prefer marrying.

Christian Bale and Drew Barrymore

Dated: 1982

It's hard to imagine Batman on a date with a quirky-cute-slightly-troubled Charlie's Angel. While Barrymore and Bale are both highly respected stars in show business, we just can't imagine their personalities clicking. He's more of the brooding, suave type, while she is awkward, eager, and slightly offbeat in a charming way. It would be like James Bond getting it in with Mary Poppins. Just plain wrong. No wonder it only lasted through one movie date.

Roger Ebert and Oprah Winfrey

Dated: 1986

She helps people put their lives back together for a living, he picks their labors of love apart in his reviews. She shares with her guests advice for how to move forward, he tells players in the movie industry how not to suck. Their pairing was the not-so-classic match between the generous supporter and the cutting critic.

Had they lasted beyond two dates, Oprah and Ebert could have joined forces to create a gladiator-style show where authors and directors would compete for their highly desirable stamp of approval.

Geri Halliwell and Russell Brand

Dated: August-September 2012

Aftet the the Spice Girls' performance during the London Olympics, all eyes were on the mega group again. Which meant the paparazzi was armed and ready to document their every move. One of Geri Halliwell's (a.k.a. Ginger Spice) moves? Dating Russell Brand, the comedian most famous for Forgetting Sarah Marshall and marrying then divorcing Katy Perry. Before that, he was well known on the other side of the pond for being Shagger of the Year, three years in a row.

Generation gap considered, this certainly caused some "WTF?" thoughts for their respective fans.

Dennis Rodman and Madonna

Dated: 1994

While both Rodman and Madonna were known for their outrageous style, they came from totally different fields. In his autobiography, Dennis Rodman even writes, "I didn't know what the hell this white megastar wanted from me." That just about sums up our sentiments as well.

Allegedly, when Madonna first met Rodman, she locked the two of them in her hotel room and said that she would not let him out. How they crossed paths, why Madonna desperately wanted his baby, and who acted on his or her desires first are all questions that will have to remain a mystery.

Mila Kunis and Macaulay Culkin

Dated: 2002-2011

Mila Kunis is insanely hot, talented, and in demand. If for some ridiculous reason you doubt the truth of that statement, refer to her presence on pretty much every publication's list of Hollywood's hottest actresses; her performances in Black Swan, Ted, and Friends With Benefits; and her upcoming roles in movies with James Franco, Clive Owen, Marion Cotillard, and Robin Williams.

Culkin, meanwhile, still looks kind of like he's 13 and has recently been involved in hard-hitting projects like a YouTube video explaining how he transformed his apartment into a painting studio and a film shot entirely on his friend's iPhone. These sound eerily like the things your kid brother might do when he's bored and Home Alone (zing!).

If you heard the rumor they were engaged, we're sure you were just waiting for the moment when she would upgrade.

Robert Downey Jr. and Sarah Jessica Parker

Dated: 1984-1991

Even Carrie Bradshaw and Iron Man as a pair would make more sense than Sarah Jessica Parker and Robert Downey Jr. The two dated when they were both young and separated because Downey, who had allegedly been addicted to drugs since the ripe age of 8, couldn't quit his rock(s) and roll(ing) ways. He says that SJP kept trying to fix him, but he wasn't having it. Why did she stick around? Maybe she needed those 7 years to get the bad boy cravings out of her system.

Courtney Love and Steve Coogan

Dated: 2005

No matter how much or how little you know about Courtney Love, you know for sure that she is loud, raucous, controversial, and into rockers. While Steve Coogan is widely known in the UK for his partying and sexual escapades, he's somehow still more on the side of nerdy rather than crazy. Maybe that impression is born more out of the awkwardness and insecurities of his fictional alter ego, Alan Partridge, than out of reality, but Courtney Love seems to have been left with the same impression, reportedly telling friends that sleeping with Partridge was "embarrassing."

There's little love left between the former couple, whose relationship was in the tabloids when Love accused Coogan of causing Owen Wilson's suicide attempt and insisted that she was pregnant with his baby, which Coogan denied.

Justin Timberlake and Fergie

Dated: 1998

Though this relationship was so far pre-Jessica Biel that it was even before Britney, it still makes us scratch our heads. However, if you consider the point in their lives they started dating, it makes just a tad bit more sense. Timberlake was just gaining momentum as a teen superstar with NSYNC and Fergie was in her own bubble gum pop group, Wild Orchid.

Brody Jenner and Avril Lavigne

Dated: Spring 2010-January 2012

Avril Lavigne is a pop rock star who enjoys dying her hair neon colors, writing whiny songs, and getting tattoos. Brody Jenner is a reality star who hosted a TV show called Bromance, dated his sunny and tanned Hills co-stars Kristen Cavallari and Lauren Conrad, and according to his Twitter, believes that "WORK HARD=PLAY HARD."

Maybe their relationship was a farcical art experiment and we're all the idiots who believed that those two characters could ever date. Or maybe not. Either way, we know for sure that they're never, ever getting back together. Like, ever. Because's she's engaged to the guy from Nickelback.

Ted Danson and Whoopi Goldberg

Dated: 1993

We can easily see Whoopi Goldberg and Ted Danson sitting at a quiet bar somewhere with a fireplace, swapping anecdotes and laughing heartily. What we can't imagine is them sticking their tongues down each other's throats. Seriously, try it.

Ashton Kutcher and January Jones

Dated: 1998-2001

Before the whole Kutcher/Demi Moore fiasco, and before he even dated the late Brittany Murphy, the former Mr. Trucker Hat was linked to January Jones, a then-budding actress who hadn't gotten her breakout role yet. Allegedly, Kutcher didn't believe Jones would have success as an actress and discouraged her from pursuing her dreams. Years after the two split, Jones landed Mad Men.

Chelsea Handler and 50 Cent

Dated: 2010

Though Chelsea Handler's love of all things rapper is well-documented on her talk show, most assumed it was all part of her routine. That is, until 2010, when Handler started dating 50 cent. The match seemed unlikely: she was raised in an upper middle class neighborhood in Jersey; he grew up across the river in South Jamaica. She loves vodka; he doesn't drink. She helped shoot a TV show; he has been shot nine times. Unsurprisingly, the two opposites didn't stay attracted to each other for long.

Tyra Banks and Will Smith

Dated: 1993-1994

When they dated, Will Smith and Tyra Banks seemed like the dream power couple. He was the huge crossover star and she was one of the biggest models of her generation. Considering how differently the two have grown up—he, the composed A-list Hollywood actor and she, the eccentric host of America's Next Top Model—the thought of them together would seem like nothing more than a crazy PR stunt.

Simon Cowell and Carmen Electra

Dated: December 2012-current

If Carmen Electra and Simon Cowell the couple were to be evaluated by Simon in some sort of meta-fantasy-world -competition, he would laugh condescendingly in their faces and eloquently send them off with, "No. Just no." The actress/model/singer/reality TV star dating the pretentious dude who'd seem to make fun of women of her profession makes very little sense.

Lance Armstrong and Ashley Olsen

Dated: 2007

This couple is such a strange combination that we're even baffled by the logistics of their brief relationship. How did they meet? Who initiated it—the steroid abusing cyclist or the pixie-like child star? What was his pickup line? "Hey sexy, I thought you were hot in that role on Full House"? Or: "I lied my way into winning a shit ton of trophies. Wanna feel my thunder thighs?"

The age difference between these two is just the tip of the strangeness. He's a now disgraced athlete, she's a tiny mogul who grew up starring in movies about dolphins and moral dilemmas like whether to tattle on her siblings. She embodied boho-chic for a time; he prefers spandex. WTF?

Tom Cruise and Cher

Dated: 1986

This pairing makes us wish there were a reality TV show that paired the weirdest characters in Hollywood together and sent them on dates. The Tom Cruise and Cher episode would be absolutely hilarious. First of all, there's the 16-year age gap. Second of all, there's the transparent, glittery outfit Cher would likely wear and Tom's reaction to it—probably a flash of his winning smile, the one that usually conceals all the batshit crazy ideas circling around inside. Finally, there's their conversation. Would she give him tips on how to dress to reinvent himself post-divorce? Would he try to recruit her into The Church? We've never wished for a time machine so badly.