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The early '00s were a weird time. Jelly shoes were in. Von Dutch hats were a status symbol. If you wanted to make a point, you'd just write it on the back of your Juicy Couture sweatpants. We were all so distracted trying to figure out the futuristic technology behind MySpace that there are tons of celebrity couples you forgot dated (or purposefully repressed) after the Y2K panic faded.
The wild lives of celebrity couples were somehow even weirder back then than they are now, especially as more and more former stars feel comfortable oversharing in the press as the '00s become part of the distant past. Don't worry, we'll refresh your memory with this list of 40 celebrity couples you probably forgot dated in the early '00s.
Bradley Cooper and Renée Zellweger dated for nearly five years, yet we have no recollection of this couple at all. The pair met on the set of their film Case 39, a film that we incidentally also do not remember at all. According to US Magazine, this 2009 thriller filmed all the way back in 2006, when Renée and Bradley started their relationship. They broke up in 2011 after The Hangover made Bradley a star, proving that men can't be trusted. The couple lived together for at least a year, and even though neither couple ever publicly admitted to the relationship, vacations and family visits were well documented in the tabloids.
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Justin Timberlake and Jenna Dewan dated after his split from Britney Spears in the early '00s. Jenna admitted to the "friends... that dated" situation (or, as a later Justin movie would dub it, Friends With Benefits) on Watch What Happens Live without a specific timeline, but it was likely when she was a backup dancer for the pop prince. The dance-off that Lifetime's biopic Britney Ever After portrayed between the future Step Up star and the "...Baby One More Time" singer never happened, but Britney and Justin's breakup was dramatic enough without it. Jenna is still good friends with Justin, so their fling probably wasn't more than two hot people briefly being hot together.
Jared Leto has dated as many as twenty-one famous women, but his 1999 to 2003 relationship with Cameron Diaz is one of his most significant past loves. The Charlie's Angels starlet and the 30 Seconds To Mars frontman were even the subjects of engagement rumors before their split, but there's not that much online about the former lovers. Cameron must have a thing for moody rock stars — she married Good Charlotte guitarist Benji Madden in 2015 after dating Justin Timberlake following her split with Jared. As for Jared, the 47-year-old is still breaking Hollywood hearts even in the late, late 2010s.
Speaking of Justin Timberlake and Cameron Diaz, these A-listers dated from 2003 until 2007. Justin met his forever-love Jessica Biel right after his split with Cameron, but Cameron dated Yankee slugger (and current husband to J.Lo) Alex Rodriguez before finding Benji in 2015. Cameron and Justin starred in Bad Teacher together in 2011 after only four years apart, but Cameron had nothing but glowing things to say about her ex to US Weekly, where she called him "bizarre and hilarious," "a genius comedian," and "the best person for the job." It's awesome to see these famous exes are on good terms.
One of the strangest TBT couples out there, Scarlett Johansson and Jack Antonoff dated in 2001 until 2003. This was before either of them had made it big while the teenagers were students at the Professional Children's School in New York City. Lena Dunham said she felt like she was hallucinating when she stumbled upon an old picture of the couple online when she was still dating Jack. Jack is currently single and looking pretty good while he's not busy forcing '80s synths into pop music where they don't belong, and Scarlett is dating SNL head writer Colin Jost.
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January Jones and Josh Groban dated from 2003 to 2006, and more than six years after that two-and-a-half year relationship ended, Josh called it his longest relationship. He low-key hasn't had another relationship last that long since. His relationship with Kat Dennings from 2014-2016 came close, but it looks like January was the love of his life. Josh has had a weird dating history since the early 2000s, being linked to Katy Perry, April Bowlby, Selma Blair, and possibly Michelle Trachtenberg. Meanwhile, January had a baby from an unknown (to us) father, strongly advocated for eating your own placenta, and started dating Nick Viall.
Kid Rock and Pamela Anderson were such an iconic part of the early '00s that there were couples' Halloween costumes based on their marriage. It's not so much that we forgot that Kid and Pamela were together, we just kind of forgot either of them existed. Pamela and Kid called off their engagement in 2003, only to get married on a yacht three years later. Their marriage lasted for four months, and Pamela told The Hollywood Reporter in 2018 that they haven't spoken since. Pamela hilariously dragged Kid for becoming weirdly conservative, and she clearly knows that she won this breakup.
Nicole Kidman is currently one-half of the cutest couple in Hollywood, but before she was loved up with country star Keith Urban, Nicole was engaged to Lenny Kravitz. The pair dated between 2002 and 2003, and Lenny talked to Mr. Porter in 2017 about how awesome Nicole is, and how glad he is that they're still friends. We love seeing healthy celebrity breakups! Lenny also thought it was really cool that Nicole got to work with his daughter, Zoe Kravitz in The Killing Of A Sacred Deer because the ex lovers got to reunite.
One of the most shocking celeb couples on this list is Natalie Portman and Moby. They dated super briefly in the mid-'00s, and Moby said that he got a lot of hate for dating the Star Wars starlet.
"As far as the very brief affair that I had with Natalie, it’s made me a target of a lot of nerd wrath,” the DJ told Spin in 2008. “You don’t date Luke Skywalker’s mom and not have them hate your guts.”
Natalie hasn't spoken much about the short-lived fling, but Moby seems to have a thing for girls half his age, going on to date Christina Ricci after their breakup.
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Kim Kardashian in the early '00s is our favorite Kim Kardashian. The tragic outfits, the offers to re-organize Paris Hilton's closet for her, the vastly different nose. They're all hallmarks of a simpler time, a better time. Something that came out of this simpler, better time was Kim's relationship with Nick Cannon from 2006 to 2007. This was before his marriage to Mariah Carey, another TBT that reminds us of the good old days. Nick told The Howard Stern Show that he dumped Kim even though she's super nice because she lied about her infamous sex tape with Ray-J existing. It's fine — Kim clearly won that breakup anyway.
Nick Lachey and Kim Kardashian dated in 2006, right before she dated Nick Cannon, and Nick claimed in 2013 that Kim was using him to get famous. Nick said to Details that Kim would tip off the paparazzi to their date locations for the free press. Oh, how the tables have turned. No one remembers 98 Degrees and everyone knows about Keeping Up With The Kardashians, so who exactly is using whom now, Nick? Nick and Kim literally only dated for about a week after his divorce from Jessica Simpson, but we honestly wouldn't be surprised if Kris Jenner was already pulling the strings back then and did, in fact, tip off the paparazzi. The devil works hard, but Kris Jenner works harder.
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P!nk's relationship with Joey Fatone would have been a huge scandal in the early 2000s... if anyone had found out about it. P!nk told Glamour in 2013 that she secretly dated the *NSYNC star while she was opening for the band on tour. She said that Joey was totally in love with her and that he asked her dad's permission to take her out for ice cream. Is this The Notebook? Are we crying right now? The pair dated briefly when P!nk was nineteen and she fondly remembers the former boy bander as a total sweetheart.
Ryan Gosling and Sandra Bullock had a sixteen year age difference when they dated in 2002 and 2003. The 22-year-old Ryan met 38-year-old Sandra on the set of Murder By Numbers, and they confirmed their relationship at red carpet events like the Cannes premiere of Murder By Numbers and the premiere of Ryan's movie The Believer. Sandra said that her relationship with Ryan helped her to chill for a sec and shake off some of her self-professed OCD tendencies. She even told Cosmo that he was like her "little Buddha." No tea, no shade, but that's kind of weird.
Spies in love? Scandal star Scott Foley and Alias badass Jennifer Garner were literally married. The couple met while filming Felicity and tied the knot in 2000. Their nuptials lasted until 2004, and Jennifer described their divorce as an implosion to Allure. Jen had nothing but nice things to say about Scott, but copped to the fact that despite the pair being "full-on grown-ups," they weren't prepared for marriage and didn't stand a chance. Jen started dated Ben Affleck soon after her divorce, and we all saw how that turned out. Here's hoping third time's a charm for Jennifer because she's amazing and deserves some good luck.
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If it made her happy, it can't have been that bad. Sheryl Crow has been through it: crazy stalkers, breast cancer, a brain tumor, and raising two sons as a single mother. No wonder we've collectively forgotten that Sheryl dated Owen Wilson from 1999 until 2001. She also dated Eric Clapton and Lance Armstrong, and she told Telegraph that she was dragged into Lance's doping allegations by a whistleblower who had claimed she knew the whole time. Sheryl's brief romance (and rumored engagement) with Owen is probably the least interesting part of her last two decades, so it's easy to see how it got swept under the rug.
Jake Gyllenhaal and Kirsten Dunst were the quintessential Hollywood It-Couple from 2002 to 2004, when Kirsten was still uber-famous from her role as Mary Jane Watson in 2002's Spiderman and Jake was still riding his indie cred wave from Donnie Darko. Kirsten met Jake through his sister, Maggie Gyllenhaal, after Kirsten co-starred with her in Mona Lisa Smile. Jake and Kirsten moved in together real quick in a million dollar Los Angeles apartment but ultimately broke up around the two-year mark. Rumor has it that Kirsten always wanted to go out and Jake only wanted to stay in, and that dichotomy is what ended their romance.
Jake Gyllenhaal was a certified hottie in the '00s, so he played the field a bit following his split with Kirsten Dunst. Jake and Natalie Portman are good friends to this day (he once called her "the Audrey Hepburn of our generation" at the Desert Palm Achievement Awards), but they likely dated in 2002 and possibly gave it another try in 2006. Jake has joked that it's impossible to pick a restaurant because of Natalie's veganism, but if that was the main issue, being vegan is super in since the late 2010s, so it'd probably be easier for the couple to find a place to eat nowadays.
Long, long, long before Jaime Dornan was the hottest (emphasis on ~hottest~) new movie star in Hollywood with his starring role in Fifty Shades of Grey, he was the unknown boyfriend of up-and-coming actress Keira Knightley, who was was about to shoot to fame for Pirates of the Carribean. They met at a photo shoot for a British jeweler because they're both ridiculously attractive and British, and some gossip sites (like The Mirror) reported that Keira actually set Jaime up with his first Hollywood agent. The next time you're gawking over Christian Grey's abs, remember that you actually have Keira Knightley to thank.
Kiera's co-star Orlando Bloom was also in a forgotten aughts relationship — this one with Kate Bosworth from 2002 to 2006. Orlando was flying high on fame from his 2001 appearance as Legolas in The Lord of the Rings: The Fellowship of the Ring, his 2002 reprisal of the role in The Lord of the Rings' second installment, and 2003's Pirates of the Carribean: The Curse of the Black Pearl. This was truly peak Orlando, congrats to Kate for locking that down when she did.
Wilmer Valderrama and Mandy Moore dated from 2000 to 2002 after meeting on a photo shoot, and Wilmer was the This Is Us star's first boyfriend. Their relationship has been pretty interesting even after their breakup because Wilmer claimed that he took Mandy's virginity and Mandy fully called him out for lying. The two managed to get past that drama, which is really mature of Mandy. They still go to Halloween Horror Nights at Universal Studios Hollywood together every year, and even though they aren't close, the former couple remains friends more than ten years after their breakup, People Magazine reported in 2018.
Wilmer Valderrama and Lindsay Lohan's relationship was creepy. Wilmer started dating her before she was eighteen, and they kept their relationship a secret until she was a legal adult, so they probably both knew what they were doing was a) illegal and b) frowned upon. The couple broke up in 2004, only a year after they went public, and while the pair was still living together. Wilmer went on to date Demi Lovato and Lindsay wrote the song "Over" from her album Speak about Wilmer after recovering from her hospitalization for exhaustion and a high fever.
Chris Evans and Jessica Biel were a fun couple. They spent one Valentine's Day skydiving, according to a 2018 interview with Esquire, sometime between 2001 and 2006. They had a long, PDA-filled relationship, and starred in the 2004 thriller Cellular and the 2006 drama London together. The couple hasn't spoken out about why their relationship ended, but back in the good ol' days, they weren't shy about sharing the happier details of their time together. Jessica fondly remembered Chris covering her bed in rose petals on her 21st birthday and how she used to cook homemade meals for the actor.
Ryan Reynolds has fantastic taste in women. He was married to Scarlett Johannson. He's currently married to Blake Lively, the best person in the world. And he almost married Alanis Morissette, who he dated from 2002 until 2007. Ryan has an eye for quality. Alanis and Ryan met at Drew Barrymore's birthday party, which is very 2002 of them, and Alanis was Ryan's first high-profile engagement. Alanis was already an icon by then — Jagged Little Pill came out in 1994 — and Ryan was best known as Van Wilder (as in, National Lampoon's Van Wilder) and was at the beginning of a prolific career.
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Imagine how insanely beautiful George Clooney and Lucy Liu's children would have been. They could have created a new race of superhuman beautiful people, but alas, their 2006 dalliance was only a fling. There were rumors that Lucy and George were together in 2000 when they hung out together at the MTV Movie Awards, a wonderful start to the new millennium, but nothing romantic between the on-again, off-again pair was confirmed until the paparazzi caught them kissing on New Year's Eve. Lucy has denied they were ever dating, but there was clearly something going on between the two A-List stars.
Rashida Jones's personal life is fascinating. Setting aside the whole "her parents are more famous than anyone else will ever be" thing, she had a kid with Vampire Weekend frontman Ezra Koenig in 2018 and she used to date Colin Jost. Who knew? Back in 2002, Rashida started dating another musician, producer Mark Ronson. The pair were serious enough to get engaged in 2003, but broke up one year later. Mark proposed through a custom-made crossword puzzle he gave to Rashida as a 27th birthday gift, which is super cute. The former power couple are both still doin' fine, just separately.
Mila Kunis and Macaulay Culkin dated for most of the early '00s from 2002 to 2010. Mila went on Dax Shepard's podcast in 2018 to talk about the split, taking basically all of the blame. Mila said she was an "*sshole" in her twenties and alludes to a mysterious, "f*cked up" thing that she did to Macaulay that ended their relationship. Mila was promoting Black Swan at the time of the split, and the breakup was her wake-up call to figure herself out. All's well that ends well: Mila is happily married to her long-time friend and costar Ashton Kutcher, and Macaulay is dating former Disney star Brenda Song.
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Alyssa Milano and Justin Timberlake dated shortly after his breakup with Britney Spears. Was this before, after, or during Justin's fling with Jenna Dewan? The world may never know. Alyssa seems like a cool girlfriend, gushing over Britney and JT's true love to Entertainment Tonight in 2015, saying they "just seemed like the perfect match!" Alyssa and Justin dated for only a few months in the '00s, and Alyssa is pretty blase about the whole thing. Alyssa wasn't surprised when Justin and Britney broke up because they were only twenty, so her short-lived romance probably wasn't all that surprising to the young star either.
Lance Armstrong has made some questionable career decisions. No, not only the doping. He also dated Ashley Olsen when he was 36 and she was only 21. His handlers reportedly wanted him to end the relationship because of bad optics, according to the Daily Mail, but the relationship burnt out on its own after a couple of months. Lance moved on to Kate Hudson, and Ashley proved that dating older men wasn't just a phase. She dated millionaire art dealer Richard Sachs, who is 28 years her elder, Johnny Depp, who is 23 years her senior, and director Bennett Miller, who is 20 years older than her.
Gisele Bündchen is happily married to Patriots quarterback Tom Brady, and their beautiful family is the least annoying thing about the fan-proclaimed NFL GOAT. Before she was happily loved up with Tom, Gisele was the most important of Leonardo DiCaprio's long-documented penchant for blonde supermodels. The couple dated from 2003 to 2005 and was Leo's longest relationship ever. Gisele opened up about her decision to dump Leo in 2019, saying that she was struggling with depression and suicidal ideations during their relationship and made the decision to do some soul-searching and adopt a healthier lifestyle. Leo, however, was content with staying the same. Gisele met Tom on a blind date one year later, and the rest is history.
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Shia LaBeouf best keep Hilary Duff's name out of his mouth! Shia loves drumming up a scandal, and in 2011 he told Details magazine that his date with Hilary was the worst he's ever had. Granted, he also mentioned that he doesn't think she was into him at all either, but Hilary is a beautiful queen and Shia should have been so lucky. The almost-couple went out to sushi and then never saw each other again. Shia didn't give a specific timeline for this horrible date or how it came about, but since he was reminiscing in 2011, safe to say it happened well before the 2010s.
Another failed celebrity date? Shia LaBeouf and Rihanna. Don't know if that massive L is such a surprise, other than the fact that Rihanna even agreed to go out with Shia in the first place. Shia isn't one to shia way shy away from talking about his failures, and he told Playboy that he did go on one date with Rihanna in 2007. Rihanna actually reached out to him, and the duo was spotted by paparazzi when they went out to dinner. Shia chalked the one-and-done date to a lack of a spark and said that the pair remains friends.
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I guess Matthew McConaughey was a gentleman because Miss. Jackson was definitely a fan in 2002. That's right, Janet Jackson and Matthew briefly dated after meeting at the 2002 Grammy Awards, where Matthew thought it was appropriate to wear flannel. The pair didn't *date* date, but Matthew was seen leaving her Bel Air mansion one morning shirtless and carrying his shoes while whistling. A bit specific with the details there, but legends of an interview where Janet admits the couple swapped more than ideas have swirled for a decade. Matthew and Janet seem to have left it on good terms, with some very friendly red carpet conversations in 2006.
Matt Damon and Winona Ryder were introduced in the late '90s by Gwyneth Paltrow. Gwyn was really close friends with Winona at the time and was dating Ben Affleck, Matt's Boston BFF. Matt and Winona actually fell apart around the same time that Ben and Gwyn did, but we'll get to that in a second. Matt and Winona went to the Golden Globes together in 2000 Matt was nominated for an award for The Talented Mr. Riply with Gwyn — talk about a power friend group. Neither couple lasted long after the show, but Winona has said since that Matt is an awesome dude and they're on good terms.
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Speaking of Ben Affleck and Gwyneth Paltrow, did anyone else totally forget that these two were seriously dating in the '00s? The couple dated on and off for three years, from 1997 to 2000. Gwyn has had some less-than-nice things to say about Ben in the press, telling Howard Stern that Ben wasn't in the right place in his life at the time to have a girlfriend, joking with Mario Batali about the celeb chef's distaste for Ben, and heavily implying to Diane Sawyer that Ben was her rebound after Gwyn's devastating split from Brad Pitt.
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It looks like couples that get arrested together don't necessarily stay together. Jennifer Lopez and Sean "P. Diddy" Combs met when Diddy was still going by "Puff Daddy" and J.Lo was still Jenny From The Block. Her debut album, On The 6, had just been released and J.Lo was freshly divorced from her actor husband Ojani Noa. People remember J.Lo's epic, everything-baring Grammy's dress better than the man on her arm, and the couple broke up in 2001 following a brief evening in jail in December 1999 regarding a shootout and the legal issues that came from it in 2000.
John Mayer and Jessica Simpson might be better describes as an early '00s couple we wish we could forget. John Mayer went through a rough patch when he followed a TMI Rolling Stone interview in 2010 with an even worse Playboy interview, also in 2010, where he called his ex-girlfriend Jessica "sexual napalm" and compared her to crack. This was also the interview where he compared his d*ck to KKK leader David Duke, you know, like a racist. Jessica is probably glad she got out in 2007. Jessica cried on Oprah when she talked about the interview and was absolutely livid about John's oversharing.
Julia Roberts and Benjamin Bratt were a huge deal in the '00s, and their breakup after four years of dating was the cause of a lot of tabloid speculation. People ultimately decided that Ben wanted Julia to slow down her movie career to start a family with him, and she didn't want to move away from New York City. Julia attributed this to being, in her words, "a selfish little brat," but she doesn't need to apologize for putting herself first during her twenties. When she met her husband Danny Moder, she was finally ready to calm down and find a balance between work and home.
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ScarJo may be happily loved up with SNL head writer Colin Jost right now, but back in 2004, she was dating My So-Called Life heartthrob Jared Leto. They only dated until 2005, but their brief romance was immortalized in photos of them getting their PDA on from LA to NYC including one hilarious photo on PopSugar where Jared is checking his phone while Scarlett is kissing him. Clearly, their relationship was doomed from the start. The pair briefly reunited in 2012 at the DNC because nothing says PDA like liberal legislating. It still wasn't meant to be, and PopSugar thinks Jared might be the mysterious perennially unavailable ex Scarlett talked about in her 2016 Cosmo interview.
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People should have been more concerned about Hilary Duff and Joel Madden. Hilary dated Joel from 2003 to 2006, and their relationship started when she was only 16. The Good Charlotte frontman was 24. Hilary has implied that she lost her virginity to Joel, which is just so cringy. After their breakup, Hilary did what she described to Cosmo as "a massive friend cleanse" at age nineteen and Joel started dating Nicole Richie within a month. Joel and Nicole are married and have two children, Harlow and Sparrow. Paper Magazine did a deep-dive and realized that not only was no one talking about Joel dating an underaged teen, but no one cared about Lindsay and Wilmer either *or* Hayden Panettiere and Milo Ventimiglia. Hayden was 17 and Milo was 29. Maybe the '00s weren't so great after all.