By Wonderwall.com Editors
6:05am PST, Nov 21, 2020
When it comes to celebrities, it can be hard to keep track of who everyone has dated over the years. We remember their first loves, their long marriages and their most high-profile breakups — but in between those are the forgotten romances. Wonderwall.com is taking a look back at some of Hollywood's most surprising couplings that you might have forgotten about, starting with this one… Talk show host Montel Williams used to date history-making Vice President-elect Kamala Harris! Montel confirmed on Twitter in August 2019 that he and the politician — who at the time was a San Francisco City Hall lawyer and a decade away from serving as California's attorney general — were an item back in 2001. "@KamalaHarris and I briefly dated about 20 years ago when we were both single. So what? I have great respect for Sen. Harris," he wrote. Keep reading for more…
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Cher might be most famously tied to her former husband, Sonny Bono, but the music icon also dated a future A-lister back in the 1980s. In fact, Cher told Andy Cohen that this actor was one of her "top five" lovers. Who could this mystery man be?
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Renee Zellweger famously dated Jim Carrey and Bradley Cooper, had a four-month marriage to Kenny Chesney and was even linked to John Stamos at one time. But on the set of "Cold Mountain," she chose to keep warm with this popular rock star. Who is he?
The White Stripes rocker Jack White had Renee Zellweger at hello. The musician made his feature film debut in the lauded 2003 drama "Cold Mountain." He was by his then-girlfriend's side when she won an Academy Award for her work in the film. (He's seen here in the background as Renee shared a moment with Christine Taylor at the 2004 Vanity Fair Oscar party following her big win.)
Emma Thompson has been married to actor Greg Wise since 2003. Before that, she was married to actor-director Kenneth Branagh, who notoriously had an affair with Helena Bonham Carter. But who was her long-term boyfriend before her marriages?
For years, Emma Thompson made "House" with fellow Brit Hugh Laurie. They dated in the late '70s and early '80s after connecting in a sketch-comedy troupe at the University of Cambridge. They've remained friendly in the decades since their split.
Before Sandra Bullock's well-documented divorce from Jesse James, she had some "Crazy, Stupid, Love" with this actor who was so much younger than her that friend Hugh Grant used to call him "the child." Who is he?
It's Ryan Gosling, who met Sandra — who's 16 years his senior — while making 2002's "Murder by Numbers." They dated from 2001 to 2003.
Lucy Liu was never serious with this A-list actor, but from Christmas to New Year's in 2005, the two were reportedly inseparable. Who's the handsome fellow?
It's George Clooney, who reportedly briefly dated Lucy Liu in late 2002. He famously ditched his bachelor status when he wed human rights lawyer Amal Alamuddin in 2014.
We always forget that before Uma Thurman was married to another famous actor before she and Ethan Hawke tied the knot. She was 20 years old when she exchanged vows with an Englishman who was in his early 30s at the time. Remember who?
Uma Thurman and Gary Oldman tied the knot in 1990 after a whirlwind courtship that ended just as quickly: They split just two years later.
After January Jones moved to Los Angeles, she hooked up with a Hollywood star who told her that she'd never make it as an actress. It's safe to say that he's not the father of the "Mad Men" star's child, but do you know who her critical old boyfriend is?
It's Ashton Kutcher, who himself went from model to actor but didn't think his then-girlfriend could pull off the same transition. January Jones went on to score an Emmy nomination and two Golden Globe nods for her work as Betty Draper on "Mad Men."
Paula Abdul was a "Straight Up" pop superstar before she reinvented herself as a judge on "American Idol," and that kind of fame is rumored to be what ended her relationship with this formerly mullet-ed TV star. So who was the dude?
It's John Stamos, whose "Full House" fame wasn't quite on par with Paula Abdul's pop star status at the time.
Before husbands Chris Martin and Brad Falchuk, and after high-profile loves Brad Pitt and Ben Affleck, Gwyneth Paltrow briefly dated this actor after the two met on the set of "The Royal Tenenbaums." Who was the extra-special co-star?
It's Luke Wilson! Sparks flew when Luke and Gwyneth Paltrow co-starred together in 2001 but their love was short-lived. The couple broke up a year later right before Gwyneth met her future ex-husband, Coldplay frontman Chris Martin.
Natalie Portman had a baby and later married her "Black Swan" choreographer, but back in the day, she briefly dated a noted musician who claimed that all hell broke loose in nerd land when he hooked up with her. Do you know who this bespectacled man is?
It's Moby, who had to fight off the wrath of "Star Wars" geeks everywhere after they learned he'd dated Padmé Amidala aka Natalie Portman.
Robin Givens had an infamously tumultuous relationship with boxer Mike Tyson, who nearly pounded in the pretty face of this actor when he showed up at her house. Who was her future A-List star boyfriend?
It's Brad Pitt, who went on to famously wed and divorce Jennifer Aniston and Angelia Jolie.
Everyone knows Britney Spears was once half of a pop power couple with Justin Timberlake. But in 2003, just before she wed Kevin Federline, Britney linked up with a foreign-born actor who had a reputation for being quite lucky with the ladies. Can you remember who it was?
Demi Moore was married to Bruce Willis for more than a decade and later married and divorced Ashton Kutcher. But in 2002, she had a summer fling with this rock star, whom Bruce allegedly wanted to take "under the bridge" and beat up. Who was the lucky guy?
Anthony Kiedis! Bruce Willis reportedly thought the Red Hot Chili Peppers rocker would be a bad influence on the three daughters he shares with ex-wife Demi Moore.
Long before she wed David Arquette or romanced current love Johnny McDaid, Courteney Cox spent six years dating this Oscar-nominated actor. The two thespians would reportedly run lines together and read over each other's scripts back in the '90s. Who is her ex-love?
It's Michael Keaton! For a long time, Courteney Cox and the "Batman" actor were totally inseparable. She later called the romance "the most important relationship I've ever had." Aww!
Liv Tyler was only 18 when she started dating this actor. Their young love was filled with romance, but eventually, the spark fizzled. Despite their breakup, Liv has said that she still considers the Academy Award winner to be "family." Who is it?
Joaquin Phoenix! Liv Tyler and the "Walk the Line" star are as amicable as exes can be, according to her. "I'm friends with all my exes! I love them so much! I guess it depends on what happens, right? I consider Joaquin and all of his sisters to be like family," she once told ELLE. "We were so young when we were together, like 18 to 21. He was my first love. So he's a huge part of even my sense of humor."
Hilary Duff is all about the mom life these days after welcoming her second child, a girl, in 2018 with musician Matthew Koma and preparing to give birth to her third in 2021 (she also has a son with ex-husband Mike Comrie). But back when she was a child star, she had a one-and-done would-be romance with a fellow kid actor who said they once had the "worst date ever." Who was this not-so-chivalrous dude?
The guy Hilary Duff briefly romanced was former Disney star Shia LaBeouf. The "American Honey" actor went on to date Carey Mulligan and "Transformers" co-star Megan Fox before marrying and divorcing Mia Goth then briefly moving on with FKA Twigs ahead of a romance with actress Margaret Qualley.
Tyra Banks was a young model getting her first big television break when she dated the princely star of a popular sitcom. He's more of an A-list king these days, and his kids are following in his all-star footsteps. So who had Tyra smizing back in the day?
It's Will Smith! The pair not only dated IRL, but their characters were a couple on "The Fresh Prince of Bel-Air."
Reese Witherspoon casually dated this handsome young actor for a few months in the early '90s — around the time his career first started taking off. Remember who?
Reese Witherspoon and Chris O'Donnell dated for a few months in 1993. After they split, he started seeing Caroline Fentress. They've been married since 1996, which is why it's probably easy to forget that the "NCIS: Los Angeles" star was ever with anyone else!
Kristen Bell might be married to Dax Shepard now, but back in college, the "Forgetting Sarah Marshall" star had a gleeful young actor who couldn't keep his jazz hands off her. Who is the now-famous fellow?
It's former "Glee" star Matthew Morrison, who swept a young Kristen Bell off her feet during their college years.
Way back in the '80s, Drew Barrymore and a fellow child star went on a disastrous date together — the mystery guy said he didn't leave the best impression. Both went on to become A-list superstars, and the guy even became a superhero. Who could it be?
Christian Bale! The Oscar winner admitted to GQ Australia that Drew Barrymore "never called again" after they went out as teens. "We went to see some bloody awful horror film, and that was the end of it," Christian said. "She never called again."
Long before she was Mrs. Chris Hemsworth, Elsa Pataky was an up-and-coming actress who dated an Oscar winner. The pair were together for three years and were so serious that the mystery man reportedly bought the Spanish star a 19th-century castle in upstate New York for her 31st birthday! Do you remember who he is?
Did you know that Carrie Underwood and Jessica Simpson have a very famous ex in common? The country music queen romanced one of football's biggest stars a year before he and the "Dukes of Hazzard" actress fell in love. Can you remember who he is?
It's Tony Romo! The former Dallas Cowboys quarterback attended the 2007 Academy of Country Music Awards with Carrie Underwood before he famously romanced Jessica Simpson the following year — which is why people often forget he dated the country star first!
Avril Lavigne was a skater girl in love with this not-so-skater boy back in 2010. In fact, this reality TV star was much more known for his Malibu ties and famous family than any pop-punk cred.
It's Brody Jenner! Once upon a time, Avril Lavigne and the reality star were quite the couple, but their clear differences caused them to split in 2012. "Avril and I are still friends who talk, and I wish her nothing but the best. … She's a great girl," Brody told the Huffington Post after their breakup.
Sarah Jessica Parker's first well-known Hollywood romance was with Robert Downey Jr., and she's been married to Matthew Broderick since 1997. But back in the early '80s, she was romantically linked to another future superstar. Sadly, the couple couldn't find the secret to a successful relationship. Who is he?
It's Michael J. Fox, who reportedly dated fellow young star Sarah Jessica Parker in the early-to-mid-'80s before later co-starring with her in "Mars Attacks!" Though there were also rumors that the two were only together for publicity…
Melissa Joan Hart was bewitched by this Canadian future A-list actor when both stars were teens. Their young love affair included one particular hot-and-heavy make-out session that Melissa wrote about in her memoir. Can you guess who he is?
It's Ryan Reynolds. Melissa Joan Hart and the Canadian actor dated when he was 17 and she was around 19. The two went on to have beautiful families with their respective spouses, Mark Wilkerson and Blake Lively.
Before she was a makeup mogul, a reality TV star or Mrs. Kanye West, Kim Kardashian West spent time romancing this former Nickelodeon star. The two reportedly split after Kim's now-infamous sex tape with Ray J surfaced. Who's her former flame?
Fergie's dating life has been super low-key since she divorced Josh Duhamel, but once upon a time, she romanced a blonde boybander. While performing in the girl group Untamed Flower, Fergie opened for and dated this singer, who quickly told her "bye, bye, bye." Who is he?
Keira Knightley has been with her husband, James Righton, for so long (since 2011) that we often forget she ever dated anyone else! Shockingly, she had a year-long romance with one of our favorite leading men a full decade before he made his major Hollywood breakthrough…
They were babies! Keira Knightley dated "Fifty Shades of Gray" heartthrob Jamie Dornan for about a year in the mid-aughts. During that time, he frequently accompanied her to hot-ticket events, like the 2004 premiere of "King Arthur" (pictured).
Before David Arquette fell in love with Courteney Cox, he dated another famous TV actress, though she shot into the spotlight a decade before the "Friends" alum. Which former child star did the actor romance in the '90s?
Alyssa Milano! The "Who's The Boss?" actress briefly romanced David Arquette in the early '90s. They made it a date night at the 1991 premiere of "Bill & Ted's Bogus Journey."
In the early '90s, Madonna dated an up-and-coming rapper who was nearly a decade her junior. They were extremely hot and heavy (despite his affinity for ice) until he dumped her after she released her "Sex" book. Who was it?
It was Robert Van Winkle, who's better known as Vanilla Ice! He and Madonna were quite the item in the early '90s until she included him in her coffee-table book. "I broke up with her after she printed that book because I was hurt to be an unwitting part of this [trashy] package," he once said. "It was disgusting and cheap. We were in a relationship yet it looked like she was [sleeping with] all these other people." Ouch!
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