The 2000s were filled with outrageous fashion, boy bands, and iconic couples like Brangelina and Bennifer (who are reportedly back on!). The latest dating buzz and scandals happening in Hollywood made some of the hottest headlines. But with no social media to document every move stars made in their relationships, a lot of love affairs and flings went under the radar.
The crazy thing about Hollywood is how many people in the same circles have dated each other. The 2000s were formative years for a lot of A-list celebrities and musicians. Many of them gained more attention due to their dating lives than their careers.
Looking back now, there were a lot of juicy celebrity couples who dated and dominated the news cycle that may be a distant memory. Some of these relationships ended on good terms, while others left bad blood between the once loved-up celebs. Take a trip down memory lane and check out these 15 celebrity couples from the 2000s you probably haven’t thought about in years.
Jessica Simpson & John Mayer
Jessica Simpson and John Mayer dated on and off from 2006 to 2010. In Jessica’s 2020 memoir Open Book, she said they broke up and got back together nine times, with John often calling things off over email. Jessica wrote that her anxiety spiked around the time she dated John and that may have had a hand in her alcohol addiction. Jessica continued and said about their tumultuous relationship, “He’d dump me, then come back saying he had discovered he loved me after all.”
Mila Kunis & Macaulay Culkin
Mila Kunis and Macaulay Culkin quietly dated for nine years from 2002 to 2011. Mila said in the podcast Armchair Expert that the relationship ended badly on her part. She said Macaulay’s fans often went crazy over him in public, which was hard to deal with. They are now on good terms and have both since moved on with other big stars of the 2000s – Mila is married to Ashton Kutcher and Macaulay and Brenda Song recently welcomed their first child.
Ryan Gosling & Sandra Bullock
Not too much is known about Ryan Gosling and Sandra Bullock’s secretive romance. The pair supposedly dated for two years in 2002 after meeting on the set of the movie Murder By Numbers. The couple sparked interest not only because of their secrecy but because of their large age gap – Sandra is 16 years older than Ryan. Eight years after the alleged breakup, Ryan confirmed they dated and even called her one of his “greatest girlfriends.”
Hilary Duff & Joel Madden
A bit controversial, Hilary Duff and Joel Madden dated for three years when she was 16 and he was 24 in 2004. Hilary has said that this romance consumed her, and in 2007 Joel said to People magazine: “People can say or think whatever they want … so in my reality, it’s kind of irrelevant. I’m always the kind of person that does the right thing and keeps my side of the street clean.” Whatever that means, it seems both of these celebs do not see any problems with their former relationship.
Scarlett Johansson & Jack Antonoff
Little is known about the brief relationship between these two now successful celebrities. They met in high school at NYC’s Professional Children’s School in 2001 and started dating — they even went to prom together! After their breakup, Jack Antonoff went on to write a bitter song called “Better Love.” They both have gone on to each have high-profile acting and music careers, so this high school fling probably hasn’t left a bruise on anyone’s ego.
Alanis Morrissette & Ryan Reynolds
Alanis Morrissette and Ryan Reynolds met at Drew Barrymore’s birthday party in 2002 and began dating shortly after. In 2004 the two Canadians got engaged. After being engaged for three years, they amicably broke things off with Alanis stating she was a “love-addict” and needed to “break the cycle.” Ryan has since only said nice things about her, even quoting Alanis’ famous song “Ironic” while promoting his film Life in a 2017 interview.
Drew Barrymore & Justin Long
The pair met on the set of the star-studded movie He’s Just Not That Into You back in 2007. They dated for about two years with Drew Barrymore reportedly ending things and being “hot and cold” with Justin Long during their relationship. Justin was so heartbroken he decided to pull out from Drew’s 2009 film Whip It. They are now on good terms though, and even engaged in some flirtatious tweets with each other in 2020.
Chris Evans & Jessica Biel
In 2001, Chris Evans and Jessica Biel started dating. They were both relatively unknown in Hollywood, but dated for five years and even starred in two movies together during their relationship. While dating, Jessica said in an interview with Cosmopolitan that they, “Always talk about [marriage]. We both want to be married, and we both want to have children.” They both have become A-listers in their own right with Chris becoming Marvel's Captain America and Jessica becoming one half of a power couple with Justin Timberlake.
Nicole Kidman & Lenny Kravitz
Actress Nicole Kidman and rocker Lenny Kravitz met in 2002 supposedly when he was her landlord. Kidman had just come off of a high-profile divorce with fellow actor Tom Cruise. She ended up secretly dating Lenny for about a year. Nicole recently let slip that they were engaged during their whirlwind romance, which was unknown at the time. The two are on good terms with Nicole even working with Kravitz’s daughter he shares with ex Lisa Bonet on the HBO show, Big Little Lies.
Kirsten Dunst & Jake Gyllenhaal
In 2002, Jake Gyllenhaal’s famous sister Maggie introduced Kirsten Dunst to him and they began a passionate relationship. The pair dated for two years, even moving in together and adopting a dog. They reportedly broke up because Jake was more of a homebody and Kirsten liked going out, among other things. Kirsten has since moved on with fellow actor Jesse Plemons, and the couple is expecting their second child together in 2021. Jake, on the other hand, is still a bachelor who has since dated several other famous women.
Renée Zellweger & Bradley Cooper
The romance between Renée Zellweger and Bradley Cooper began in 2009 and lasted two years. They had reportedly met in 2006, while Bradley was married to Jennifer Esposito, and were friends at the time. While together, they got so serious that they moved in together and Renée had a close relationship with Bradley’s parents. They seemed to have remained friendly after their split, with Bradley stating he had “learned so much” from her and her acting skills.
Lindsey Lohan & Wilmer Valderrama
The famous pair was rumored to have started dating when Lindsey Lohan was 17 and Wilmer Valderrama was 24, but they didn’t announce their relationship until she turned 18. Wilmer is credited as being Lindsey’s first high-profile boyfriend and they were together for about a year. During their relationship, Lindsey was hospitalized twice for exhaustion and guest-starred on Wilmer’s show That’s '70s Show. Rumor has it that Wilmer broke up with Lindsey so he could date Ashlee Simpson, though that has never been confirmed.
Kate Hudson & Dax Shepard
In 2007, superstar Kate Hudson and up and coming comedian Dax Shepard dated for only a few months. In 2019, Kate went on to Dax’s podcast Armchair Expert and discussed their relationship and how the relationship started out too fast but was ultimately fun, leaving no hard feelings between the two. Dax relayed how he felt stuck in his career compared to Kate’s booming one, and that the two were just on different paths.
Joe Jonas & Ashley Greene
In 2010, fresh out of a relationship with fellow Disney star Demi Lovato, Joe Jonas began dating Twilight actress Ashley Greene. Ashley is known as being Joe’s first serious relationship, and they ended up dating for almost a year. Ultimately, having a long-distance relationship after Joe moved to Los Angeles while Ashley was in Vancouver shooting the next Twilight film was a big factor in ending the relationship.
Penelope Cruz & Matthew McConaughey
The famous costars started dating in 2005 and were together for about a year after meeting on the set of the hit movie Sahara. Not much is known about their secretive relationship, besides the fact that they road-tripped to Mexico and Matthew McConaughey called her, “a great listener.” It was reported that they ended their relationship due to their own busy schedules and there was no animosity.
