15 Forgotten '90s and Early 2000s Couples That You'll Want to Stalk Again
After watching old flames Jennifer Lopez and Ben Affleck rekindle their romance and get married, we took an obligatory walk down memory lane to revisit other iconic '90s and early 2000s couples we've been keeping in the back of our minds.
Nostalgia seems to always be a dominant narrative in the worlds of fashion and pop culture. 2022 is no exception, as inspiration from the 1990s and 2000s are taking over. Iconic shoes and accessories are raiding the closets and Instagram feeds of fashion lovers worldwide, and the valiant efforts of stars like Bella Hadid have launched a resurgence of items like low-rise jeans.
With the recent rekindling and marriage of Jennifer Lopez and Ben Affleck, we were feeling nostalgic for more than just fashion. We wanted to remind the world of all the forgotten '90s and early 2000s couples that marked the time, even if they weren't meant to be together to this day—but congrats, Bennifer!
Do you remember in 2020, when the SAG Awards brought Brad Pitt and Jennifer Aniston back together for a brief moment? The surrounding energy got us remembering all the other celebrity romances that still provide us with iconic throwback photos (and the occasional meme) to obsess over to this day. Do you remember when Tom Cruise dated Cher? That Julia Roberts and Matthew Perry were an iconic '90s couple for some time? And that Ryan Reynolds, who's now enjoying life with Blake Lively and their three daughters, once dated singer Alanis Morissette? You might search for some of these famous '90s couples from time to time to reminisce, while others might pop up on your Instagram feed thanks to accounts like @90sanxiety. But beyond whatever you've come across lately, some of the couples below are sure to surprise you with the reminder that yes, those two celebrities really dated.
So, if Bennifer's got you searching for a dose of nostalgia, take a look back at the magic of these 15 forgotten '90s and early 2000s couples, whose high-profile relationships became synonymous with their equally talked-about era.
Sarah Jessica Parker and Robert Downey Jr.
Sarah Jessica Parker and Robert Downey Jr. met on the set of the film Firstborn in 1984. They quickly formed a relationship and went on to date for seven years, barely reaching '90s couple status before parting ways in 1991.
Tom Cruise and Cher
Tom Cruise and Cher met at the wedding of Sean Penn and Madonna in 1985. At the time, she was 39 and he was 23.
Kate Moss and Johnny Depp
Picture-perfect '90s couple Kate Moss and Johnny Depp dated from 1994-1998 and broke up shortly after getting engaged.
Julia Roberts and Matthew Perry
Julia Roberts and Matthew Perry met during the second season of Friends in 1996, when she made a cameo. This '90s couple's romance was quick, but it was pretty iconic while it lasted.
Brad Pitt and Christina Applegate
Brad Pitt and Christina Applegate appeared together at the MTV Movie Awards in 1989.
Gwyneth Paltrow and Ben Affleck
Gwyneth Paltrow and Ben Affleck dated on and off from 1997 to 2000. Paltrow later reflected on the relationship as a time she was "looking for healing" in her life.
Brad Pitt and Jennifer Aniston
Brad Pitt and Jennifer Aniston met in 1998 and were married from 2000-2005. The two had an iconic reunion at the 2020 SAG awards, which left fans dreaming of their past fling.
Cameron Diaz and Jared Leto
Cameron Diaz and Jared Leto were together between 1999 and 2004, and they even got engaged. But the '90s couple's engagement ultimately ended, and Diaz started dating Justin Timberlake soon after.
Sofia Coppola and Quentin Tarantino
Sofia Coppola and Quentin Tarantino dated after Coppola separated from Spike Jonze in 2003.
Janet Jackson and Matthew McConaughey
Janet Jackson and Matthew McConaughey had some romantic encounters revealed during an episode of Watch What Happens Live, and nothing seems to get fans excited more than a '90s couple's reunion.
Ben Affleck and Jennifer Lopez
While Bennifer has been making headlines recently, until a year ago, their relationship flew under the radar. With marriages and flings in between, it can be easy to forget that their romance began budding years ago. The two first met in the early 2000s on the set of the film Gigli, and by November of 2002, the two were engaged (for the first time). But by January of 2004, the two were officially separated. It wasn't until years later, in 2021, that they would rekindle their romance.
Ryan Gosling and Sandra Bullock
Ryan Gosling and Sandra Bullock dated between 2002 and 2003, when she was 38 and he was 22.
Ryan Reynolds and Alanis Morissette
Ryan Reynolds and Alanis Morissette met on Drew Barrymore's birthday in 2002 and got engaged in 2004. In 2006, however, they broke up, and they've since lived semi-parallel lives by getting married and having three children.
John Mayer and Jessica Simpson
John Mayer and Jessica Simpson dated in 2006. In a controversial interview for Playboy in 2010, Mayer stated, "This girl was like cocaine to me."
Bradley Cooper and Renée Zellweger
Bradley Cooper and Renée Zellweger dated for two years, from 2009 to 2011. While their romance was more recent than the mostly '90s couples on this list, it was just as iconic.
