Forgotten celeb couples of the 2000s

By Wonderwall.com Editors 5:04am PDT, Jul 24, 2020

The aughts — that decade at the start of the millennium — doesn't seem like that long ago, until, of course, you start to think about all the events that occurred during that time period. Join Wonderwall.com as we take a look at the forgotten celeb couples of the 2000s… Sure, Chris Evans has since dated several Hollywood stars including Minka Kelly, Jenny Slate and Lily James, but there was a time when the apple of his eye was Jessica Biel! The "Captain America" leading man romanced the "7th Heaven" actress from 2001 to 2006 while she starred on the hit family drama. Chris was pretty romantic, Jessica — who's now married to Justin Timberlake — has admitted. "When I turned 21, I actually awoke to find my bed covered in rose petals," she told Cosmopolitan in 2005. "In the middle of the night, he had pulled apart at least 24 roses in all different colors and sprinkled the petals everywhere. He's definitely a keeper." Keep reading to check out more forgotten relationships of the 2000s!

Jessica Simpson and John Mayer dated from 2006 to 2007. In Jessica's 2020 memoir "Open Book," she detailed how she went back to the "Gravity" singer on more than one occasion. "We were great at intimacy. We were great at loving each other," she told Hoda Kotb on the "Today Show." "That was easy, but the relationship was very complex. And it was always on-again, off-again. On-again, off-again. And I went back close to nine times." Jessica's roller coaster romance with the singer-songwriter was also a factor in her split with Tony Romo. "[Tony] accused me of seeing John behind his back… I hadn't cheated on Tony at all, but I could not lie and say I hadn't even seen him." Sounds messy.

Yup, there was a time when Scarlett Johansson and Josh Hartnett were an item. The duo got together after co-starring in "Black Dahlia" in 2006 but ended things just a year later due to their busy schedules. According to Josh, the breakup was "really painful." The actor has said of the split: "At the end of the day we're just ordinary people, and it didn't work." The same year he split from ScarJo, the "Pearl Harbor" actor was linked to Helena Christensen, Penelope Cruz, Sienna Miller and Gemma Ward.

RELATED: 2000s movies to stream at home

How cute was this early aughts couple? Long before Jamie Dornan sizzled on screen in "Fifty Shades of Gray," he was in a relationship with actress Keira Knightley from 2003 to 2005. Jamie went on to marry Colin Farrell's ex, singer-songwriter Amelia Warner, in 2013 and the couple now share three kids. After Jamie, Keira dated "Homeland" star Rupert Friend for five years before marrying musician James Righton in 2013. They welcomed their second child in 2019.

There was drama in teenybopper land back at the turn of the millennium when pop singer Aaron Carter was dating singer-actress Hilary Duff and then did a switcheroo and started seeing Lindsay Lohan in 2003. Then he got back with Hilary, only to allegedly cheat on her with her best friend.

Nowadays, Hilary Duff is happily married to musician-producer Matthew Koma while Joel Madden found his bride in Nicole Richie. But back in the aughts, the "Lizzie McGuire" star and the Good Charlotte rocker dated each other! Hilary and Joel were in a relationship for three years from 2003 to 2006, though they only went public with their romance after her 18th birthday, given that she was eight years his junior. "I had a 26-year-old boyfriend," she later told Cosmopolitan of losing her virginity. "So everyone can make their own assumptions about what I was doing."

Sociality and reality star Paris Hilton and Backstreet Boy Nick Carter dated for seven months in 2004 and their romance was packed with allegations of cheating, abuse and all sorts of drama. It's seems crazy now, but back then they were, like, a really big deal.

Tara Reid was an "It" girl once upon a time, and JC Chasez was a heartthrob member of *NSYNC. When he went solo in 2002, she starred in his "Blowin' Me Up" video, and they tried to become an "It" couple. The math didn't add up and even though they went to the 2002 Billboard Music Awards together, they were not meant to be.

Before there was Scarlett Johansson and Blake Lively, there was Alanis Morissette! Ryan Reynolds met the Canadian singer-songwriter in 2002 at Drew Barrymore's birthday bash. They got engaged two years later in 2004 but called it quits three years after that in 2007. "I think it's the straw that breaks the camel's back," the "Ironic" singer told the Los Angeles Times of her breakup with the Canadian actor. "I was a full-blown love addict, so it was like, 'I can't keep doing this, my body can't take it.' For someone who is a love addict, [breakups are] debilitating." Alanis's 2008 album "Flavors of Entanglement" addressed the demise of their passionate romance.

It's hard for us to forget one of the greatest relationships of the 2000s — Ryan Gosling and Rachel McAdams — but people do forget. They dated for two years after filming "The Notebook" together, split in 2007, then tried one more time in 2008 before calling it quits again. She's since welcomed a child with screenwriter Jamie Linden while Ryan is a daddy of two with girlfriend Eva Mendes.

Orlando Bloom and Kate Bosworth broke up in 2006 after about three years of dating. Years later, Kate claimed that the pain of the split gave her vertigo. She's now married to director Michael Polish, while Orlando is with Katy Perry after splitting from first wife Miranda Kerr in 2013.

After meeting while filming the 2002 psychological thriller "Murder by Numbers," Ryan Gosling and Sandra Bullock were in a relationship for almost two years. While neither confirmed their relationship at the time, the "La La Land" actor eventually admitted that he did date the "Miss Congeniality" actress. However, despite being very much smitten with one another (Ryan even went so far as calling Sandra one of his "greatest girlfriends"), their relationship was the subject of some scrutiny due to the fact that Sandra was 37 while Ryan was 21 when they were first romantically linked.

This one might have slipped by you! Nick Lachey and Kim Kardashian West briefly dated in 2006. Nick later suggested to Details magazine in 2013 that Kim used him for fame. While we're not shocked, she definitely got what she was looking for!

From 2003 until 2010, "Home Alone" star Macaulay Culkin had Mila Kunis by his side. "We grew up together," she said before their split. "You find a steady rock in your life and that's all you need. We have our ups and downs but work through them." Mila married Ashton Kutcher in 2015 and the couple now share two kids. As for Macaulay, he's been in a relationship with former Disney star Brenda Song since 2017.

"The O.C." stars Adam Brody and Rachel Bilson started dating in real life during the first season in 2003. They were besties in love and they even adopted a pit bull terrier together before calling it quits in 2006. Adam has been married to Leighton Meester since 2014 and the couple welcomed their first child in 2015. Rachel split from longtime beau Hayden Christensen, with whom she shares a daughter, in 2017. She briefly dated Bill Hader in 2019 and 2020.

"Dawson's Creek" meets "American Pie"? Before Tom Cruise was ever in the picture, Katie Holmes famously started dating Chris Klein in 2000 after meeting him on the set of her hit teen series. The young couple got engaged three years later in 2003. They called it quits in March 2005. Some criticized Katie for getting engaged to future ex-husband Tom just three months after her split from Chris was reported, but Chris has explained that the timeline is off. "When we were breaking up, we kept it to ourselves for a while. It looked like it was Katie and Chris together and two seconds later Katie and Tom together, but that's ridiculously compressed… Kate was incredibly respectful about the decision she was making to move on [with Tom]," he told People.

Four days after splitting with hairstylist husband Ric Pipino in 2002, Heidi Klum popped up in Australia with Red Hot Chili Peppers frontman Anthony Kiedis. It was a quick fling and by 2003, she was pregnant with Italian businessman Flavio Briatore's daughter. Heidi is now married to musician Tom Kaulitz after splitting from second husband Seal in 2012. And Anthony is still dating young models.

Janet Jackson and Matthew McConaughey? It's true, they were a couple… sort of. The "All for You" singer dated the actor in 2002 after meeting him at the Grammys. While Matthew denied ever being involved with the music star, insisting they were "just friends," Janet later admitted to the brief romance. In 2019 during a game of Plead the Fifth on "Watch What Happens Live," Matthew was asked to either confirm or deny his relationship with Janet. After nervously laughing, he said, "We went and had dinner one night. That was sort of it."

Now that she's married to choreographer-dancer Benjamin Millepied, it's hard to remember that Natalie Portman had a dating life before "Black Swan." But from 2003 to 2004, she was with Gael Garcia Bernal, whom she met while working on an independent film in 2003. They gave it a second chance nine months after a breakup, but it didn't work out. Natalie was also famously linked to Jake Gyllenhaal in 2002 and again in 2006.

"American Idol" alum Carrie Underwood and Dallas Cowboys quarterback Tony Romo dated in 2007, but it's often forgotten because he went on to date Jessica Simpson in 2008 and 2009. Carrie switched sports and in 2010 married hockey player Mike Fisher, with whom she shares two boys. Tony, who retired from the Cowboys in 2017, now has three children with wife Candice Crawford.

Nothing says "awesome start to a relationship" better than a New Year's Eve hookup, but that's what allegedly happened with Jessica Alba and Mark Wahlberg, who reportedly got together at the Shore Club in Miami Beach before the clock struck midnight on Dec. 31, 2003. When the champagne wore off, so did the romance. He was on a break from Rhea Durham, his now-wife and mother to his four children. And Jessica has since moved on with husband Cash Warren, the father of her three girls.

Gisele Bundchen and Leonardo DiCaprio got together in 2001 and there were some engagement rumors in 2004, but the couple called it quits in 2005. Gisele and NFL quarterback Tom Brady are now happily married with children. As for perpetual bachelor Leo, he went on to romance many more models.

Just like there was life for Gisele Bundchen before Tom Brady, there was sexy time for Tom Brady before Gisele. From 2004 until the end of 2006, Tom dated actress Bridget Moynahan. And, just like her character in "Serendipity," she was ditched. But Bridget was pregnant when they split. She gave birth to the couple's son, John Edward Thomas Moynahan, in 2007. Tom now has two kids with Gisele, whom he married in 2009.

Bradley Cooper and Jennifer Esposito's four-month marriage came to an end in 2007 because, as Bradley told radio host Howard Stern, "It just wasn't right. It's interesting… things happen!" In 2019, Bradley called it quits with model Irina Shayk, with whom he shares a daughter. Jennifer later married and divorced British model Louis Dowler.

Ashlee Simpson and singer-songwriter Ryan Cabrera dated in 2004, back when she was starring on her eponymous MTV reality show. During that year, she also screwed up her performance on "Saturday Night Live," so her breakup with Ryan was less of a milestone. She then married Fall Out Boy bassist Pete Wentz in 2008 and welcomed a son the same year. Ashlee has been married to Evan Ross, since 2014. As for Ryan, he was last linked to WWE star Alexa Bliss.

Nicolas Cage was a huge Elvis Presley fan, so it was a big deal when he married The King's daughter, Lisa Marie Presley, in 2002. But they split less than four months later. "I'm sad about this, but we shouldn't have been married in the first place. It was a big mistake," she said through her publicist.

After meeting making the 2002 comedy "Gigli," in which they both starred, Jennifer Lopez and Ben Affleck began a whirlwind romance (remember when he appeared in her "Jenny from the Block" music video?). In a matter of two years, Bennifer went from casually dating to a broken engagement and finally called it all off in 2004. "I lost my sense of self, questioned if I belonged in this business, thought maybe I did suck at everything, and my relationship [with Ben] self-destructed in front of the entire world," she told Vanity Fair years later. She went on to marry and divorce Marc Anthony and is now with baseball star Alex Rodriguez.

Kate Winslet and director Sam Mendes were London lovers until they ended their nearly seven-year marriage in 2010. (That's what happens when some couples of the aughts try to extend into a new decade.) Some reports claimed it was over because he got too close to actress Rebecca Hall. Kate married third husband Edward Abel Smith in 2012.

January Jones was an unknown actress in 2000 when she was dating Ashton Kutcher of "That '70s Show" fame. If it were up to him, she would have been an unknown forever. "He was not supportive of my acting," January told GQ in 2009. "He was like, 'I don't think you're going to be good at this.'" Well, the "Mad Men" star sure proved him wrong!