If you’re looking for unpredictable and highly erratic entertainment, it doesn’t get better than Hollywood romances. Elopements, secret dating, sudden marriages that last a lifetime, and long marriages that explode gloriously. Where fame and fortune mixes with the search for The One, there’s bound to be some scalding hot tea – as evidenced by these 42 bizarre couples.
1. Mission: Date Cher
This is almost a two for one. More people than Madonna and Sean Penn got together at the superstars’ 1985 wedding. Two wedding guests also started flirting: Tom Cruise and Cher. The diva and the young action star struck up a conversation, reconnected at a White House event, and soon enough, they were an item. It didn’t last long but dang is it a good Hollywood footnote.
2. Kill Gary
Kill Bill actress Uma Thurman and Harry Potter’s godfather Gary Oldman took a stint into marriage despite their 12-year age difference. They lasted two years before divorcing, and both have moved on since. Thurman lasted seven years with Ethan Hawke and Oldman is on his fifth marriage.
3. Does Hogwarts Have a Glee Club?
Can you picture Hermione and Sam from Glee having a tete-a-tete? Well, it happened! Chord Overstreet and Emma Watson dated briefly in 2018. Spotted in Los Angeles in February of that year, they just managed to scrape it ‘til May.
4. Mumford and Bride
The lead singer of Mumford & Sons, Marcus Mumford, and British actress Carey Mulligan have quite the meet-cute. Apparently, the couple met through a childhood pen pal program. After getting back in touch as adults, they tied the know in 2012. They have two children and keep their relationship locked and barred from the public eye. Mulligan has said, “Marcus is the only thing that’s mine that I can keep totally away, so I try to.” Oh, and another member of the band is married to Dianna Agron from Glee.
5. Fiona Gets Her True Love’s Kiss
After dating Justin Timberlake and Jared Leto, Cameron Diaz surprised everyone by marrying rock-star and Good Charlotte guitarist Benji Madden. The private couple kept their relationship out of the public eye for some time, but Madden officially ruined that in 2017. That’s when he posted on social media for his wife’s 45th birthday.
6. Sophisticated Lady
Back in the 2000s, Nicole Kidman was back on the market after her divorce from mega-star Tom Cruise. The Aussie actress started dating Lenny Kravitz, most famous for a few competing reasons: a) rock music b) wearing an extremely long scarf c) a certain NSFW concert moment and d) being Zoe Kravitz’s dad. He also apparently wrote the extremely catchy song “Lady” for Kidman. Though the couple even got engaged, they ended up parting ways.
7. RDJ Loves SJP
Classic love story: boy meets girl, they fall in love, they both pursue Hollywood careers, boy struggles with substance abuse, and boy and girl break up. Robert Downey Jr. and Sarah Jessica Parker were the young Hollywood couple in the 1980s, but sadly, they couldn’t make it through some very tough times: Downey Jr’s descent into addiction.
After a serious, seven year relationship, the young actors broke up, though they only had good things to say about one another. They even recently reconnected to give each other closure. Pass the tissues.
8. The Name’s Bond; Rachel Bond.
Daniel Craig and Rachel Weisz have been together for a whopping eight years (practically a century in celebrity-marriage world). Maybe that’s a result of keeping their relationship so private. Weisz once said to More magazine, “You have to protect your marriage.” One thing we do know? Weisz recently gave birth to the couple’s first child at 48 years old.
9. Too Bad She’s Taken
1980. Dublin. Ardmore Studios: a sorceress approaches a young man who is immediately entranced. There’s just one thing: this is the set of Excalibur, the sorceress is a young Helen Mirren (dressed up as Morgana Le Faye), and the man is Liam Neeson. After Mirren’s entrance knocked Neeson’s socks off, the actors quickly hooked up, even living together for a time. While they aren’t together anymore, they’re still on good terms. D’aww.
10. I See Love in Your Future…
This one’s for the kids who grew up in the 2000s. Who remembers Raven Symone from That’s So Raven and her girlfriend, America’s Next Top Model contestant, Azmarie Livingston? They’re an on-again off-again couple that, last was heard, is still together.
11. Sotto Voce Service
Dave Franco and Alison Brie got married in a secretive wedding service some two years ago. They wanted it to be as low-key as possible, and it looks like that worked!
12. Mum’s the Word
When Katie Holmes split from her former husband Tom Cruise, an unlikely suitor was there to scoop her up: Jamie Foxx. That being said, the couple has been extremely tight-lipped about their relationship, with Foxx even cutting an ESPN interview short when asked about it. Rumor has it that all that secrecy went to waste. Sadly, the couple is no longer together.
13. Saturday Night Love
This one’s sweet. Funnyman Andy Samberg and critically acclaimed folk musician Joanna Newsom are one of Hollywood’s most low-key, steady couples. Even though he’s a comedian and she’s broody singer, the duo clearly make it work. They extremely private couple recently welcomed their first child.
14. Nerds, Prepare to Lose it
Here we go: River Song (Alex Kingston) and Lord Voldemort (Ralph Fiennes) were married between 1993 and 1997. Gilderoy Lockhart (Kenneth Branagh) and Professor Trelawney (Emma Thompson) were the British power-couple from 1989-1995, until Lockhart started making dark magic with Bellatrix Lestrange (Helena Bonham-Carter).
Oh, and Ginny Weasley (Bonnie Wright) was engaged to Grindelwald (Jamie Campbell Bower).
Bonnie Wright and Jamie Campbell Bower
15. Slow n’ Steady
Jim Parsons, most famous for playing Sheldon on The Big Bang Theory, tends to keep his private life private. The comedian was actually with his husband Todd Spiewak for 15 long years before they put a ring on it. Parsons said in an interview with Stephen Colbert, “We just didn’t care about the act of it that much, to be honest with you.”
16. Mail-Order Husband
Mockumentary director Christopher Guest jokes that his wife, Jamie Lee Curtis, picked him out of a magazine. As the story goes, Curtis told a friend, “I’m going to marry that guy,” when looking at his photo. She was right: The picture still hangs in their home.
17. Maeby They’ll Find Love
This one is very unexpected: Brad Pitt has been seen out and about with Alia Shawkat, a young artist and actress best known for playing Maeby Funke on the cult hit Arrested Development. Honestly, I ship it.
18. She’s Everybody’s Type, That’s Her Thing
Oh, Jackie Burkhart: You were truly the best part of That 70’s Show. But apparently, Mila Kunis’ charms extended off screen as well. Before marrying her 70’s Show co-star Ashton Kutcher, Kunis was in a long-term relationship with troubled ex-child star Macaulay Culkin.
19. When Meg Met Dennis And Then Met Someone Else
Remember when Meg Ryan was married to Dennis Quaid? They seemed like the golden couple–but behind closed doors, life was dark indeed. Quaid struggled with substance abuse issues and Ryan was rumored to seek comfort in the arms of her young Australian co-star: then up-and-coming actor Russell Crowe. Ryan and Crowe became an item shortly after Quaid and Ryan announced their split, but they didn’t last.
20. You Oughta Know
Here’s a wayback playback. In the early 2000s, Canadian lovebirds melded the best of screen and sound. Songbird Alanis Morissette adored her younger boyfriend, fellow Canuck Ryan Reynolds. And while we’re here, let’s address the elephant in the room. Alanis’ ultimate break-up song “You Oughta Know” is reportedly about another one of Morissette’s exes: Dave Coulier, aka benign-seeming Uncle Joey from Full House. We guess in real life, he had Uncle Jesse-style bad boy moves.
21. She Went To The Candy Shop
I have a soft spot for this one: Chelsea Handler shared what seemed to be a very tender relationship with rapper/business mogul/professional petty man 50 Cent. Even though Handler said, “I’m not gonna date somebody whose name is a number,” they struck up an unlikely romance in 2011, with both parties still speaking fondly of one another.
22. Keeping Up With A Messy Man
Basketball player and chronic mess Lamar Odom has been through…a lot so inevitably, some drama was going to get lost in all the kerfuffle. Few people know that he left a very famous woman for Khloe Kardashian. In 2009, Odom walked away from the goddess herself, Taraji P. Henson.
23. Community of Two
This one’s kind of niche but come along for the journey anyway. Fans of Community will remember Shirley, the squeaky-clean Christian mom played by Yvette Nicole Brown, but few people know that she dated a superhero: Zachary Levi, aka Shazam! The couple attended several events together in 2011 and looked very cute.
24. A Star Is Dumped
For all the Bradley Cooper/Lady Gaga romance rumors that have been swirling since A Star Is Born, it’s worth pointing out that Cooper has already dated a glamorous blonde triple threat: Renee Zellweger. The Hollywood actors dated for two years before splitting, apparently because of Cooper’s accelerating career.
25. La La Love
Emma Stone started dating SNL writer and director Dave McCary sometime after her appearance on the show in 2016. McCary direct Stone in a sketch. They’ve been mostly private, only making their public debut as a couple at the 2019 SAG Awards.
26. Marvel vs DC
Serious Black Widow and goofy Deadpool probably wouldn’t get along in the comic book universe and clearly, they didn’t get along in real life either. After a whirlwind romance, Ryan Reynolds and Scarlett Johansson tied the knot in 2008, only to divorce in 2011. Soon after, Johansson used a strange word to describe their doomed romance, cryptically saying it was a “competitive” union. Hmm.
27. Political Promiscuity
Rosario Dawson and Senator Cory Booker (who previously made moves on Mindy Kaling via Twitter) were spotted attending Dear Evan Hansen in January 2019. It was only a matter of time before the public demands for confirmation found Dawson spilling the beans to TMZ. The actress said, “I am just grateful to be with someone that I respect and love and admire so much.”
28. Mr and Mrs Smith
Before settling down with Jada Pinkett Smith, Will Smith formed half of one of the 90s’ ultimate super-couples by dating Tyra Banks. Between 1993-1994, the iconic supermodel met the Fresh Prince himself while on set of the comedy show. Before Jada got serious with Smith, she dated Wesley Snipes and Tupac. Strong dating histories, these two.
Oscar-winning actress Helen Hunt tried out 17 months of marriage with a very unlikely catch. She briefly settled down with Hank Azaria (known for playing several characters on The Simpsons, including Moe, Apu, and Chief Wiggum). It did not last, and they split in 2000.
30. When You Know, You Know
There’s couples who move fast, and then there’s Nicolas Cage and Patricia Arquette. Apparently, Cage was so smitten that he proposed on the same day that they met. It’s therefore downright confusing that they lasted five years before divorcing. All things considered, that’s not a bad marriage-span and a very impressive dating: marriage ratio.
31. From Tennis Court to Divorce Court
Brooke Shields’ marriage to tennis star Andre Agassi came to a screeching halt in 1999 after two years of marriage. And there are certain things Shields won’t forget readily. In her 2014 memoir, Shields revealed the couple’s darkest moment. When discussing Agassi’s confession of his addiction to crystal meth, she wrote, “I was the one who had supported him unconditionally when he told me that he was basically bald and had been wearing hairpieces most of his adult life. Why should this have been any different?”
32. Blood Bond
When Angelina Jolie and Jonny Lee Miller married, Jolie apparently wore a white shirt with Miller’s name written on the back…in her blood. This is grounds enough for everyone to be pleased about their divorce.
33. Jurassic Anatomy
After spending plenty of time together on set working on various projects, Geena Davis and Jeff Goldblum tied the knot in 1987. Davis filed for divorce based on “irreconcilable differences,” and if that doesn’t leave you thirsting to know what she meant then what are you even doing here.
34. Canadian Content
These days, the shine has kind of worn off Canadian Prime Minister Justin Trudeau, but remember back in 2015 when he was everyone’s political boyfriend? Turns out dude got his charisma from his dad. When Justin’s father Pierre Elliot Trudeau was Prime Minister of Canada, he charmed one of Hollywood’s biggest stars: Barbra Streisand. The pair were briefly an item in the 70s.
35. Marriage of Unequals
Richard Gere and Cindy Crawford were married for four years. In a 2014 interview, Crawford said they were never really peers in their marriage. In her words, “I was young and he was Richard Gere.”
36. Big Little Liaisons
Talk about a weird match; actress Laura Dern was married to rock/soul/reggae musician Ben Harper. The marriage was tumultuous, with Harper filing for divorce, the pair reconciling, and Laura filing for divorce all in the span of three years. This also seems like the right moment to break it to you that Counting Crows frontman Adam Duritz dated Emmy Rossum, Courteney Cox, and Jennifer Aniston. The 90s were weird.
37. “I’ve Got a Beau For You”
Zooey Deschanel and Death Cab For Cutie frontman Ben Gibbard were introduced by their music manager. Sadly, it seems the manager kind of screwed the pooch on that one. Their marriage only lasted approximately three years. Nowadays Deschanel is dating one of the Property Brothers.
38. Bae Watch
Everything about Pamela Anderson’s marriage to Robert James Ritchie (better known as Kid Rock) was spectacular; from their party yacht wedding in St. Tropez, to their short-lived marriage, to the fact that Anderson claims not have spoken to her ex-husband since the divorce.
A good sense of humour goes a long way – maybe that’s what got Pete Davidson an in with Kate Beckinsale. The flirtation allegedly began at a party for InStyle, where Beckinsale neglected the company of anyone else in favour of flirting with Davidson. They’ve since split, but we’ll always remember the memes.
40. More People Need To Know
More people need to know that Whoopi Goldberg and Ted Danson dated in the 1980s. After Danson and Goldberg fell in love while co-hosting an environmental video, Danson and his wife divorced and the new couple struck up a relationship. But they were doomed to an absolutely cringe-inducing end. Danson performed a comedy routine about the couple’s unexpected romance…while in blackface. It’s safe to say that it did not go over well. Unsurprisingly, the couple didn’t last.
41. XOXO, Gossip Girl
After all of the Nate and Chuck drama, Blair Waldorf settled down with an unexpected choice: The OC’s Seth Cohen. Leighton Meester and Adam Brody have been married since 2014, having their first child only a year later.
42. The Handmaid’s Fairy Tale
Why do the SNL guys keep marrying their show’s hosts? Elisabeth Moss and Fred Armisen were married for eight months, an experience Moss has since described as “traumatic.” Armisen has also confessed to being a “terrible husband.”