14 '90s Couples That You'll Want To Stalk Again

After watching the now-famous reunion between old flames Jennifer Aniston and Brad Pitt at the SAG awards, we took an obligatory walk down memory lane to revisit other iconic '90s couples we've been keeping in the back of our minds
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Nostalgia seems to always be a dominant narrative in the worlds of fashion and pop culture, and 2019 was no exception as inspiration from the 1990s and 2000s took over. Iconic shoes and accessories took over the closets and Instagram feeds of fashion lovers worldwide, and the valiant efforts of stars like Bella Hadid even almost brought back low-rise jeans.

Aligning with the rose-coloured glasses we have on the turn of the millennium, we wanted to remind the world of all the forgotten '90s couples that marked the time, even if they weren't meant to be together to this day. Recently, the SAG Awards brought Brad Pitt and Jennifer Aniston back for a brief moment, and 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.

Here, we remember the magic of these 14 forgotten '90s couples, whose high-profile relationships became synonymous with their equally talked-about era.

Kate Moss and Johnny Depp

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Picture-perfect '90s couple Kate Moss and Johnny Depp dated from 1994-1998 and broke up shortly after getting engaged.

Brad Pitt and Jennifer Aniston

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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, and now that both are single again, who knows what might happen?

Julia Roberts and Matthew Perry

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The duo 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.

Tom Cruise and Cher

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Cruise met Cher at the wedding of Sean Penn and Madonna in 1985. At the time, she was 39 and he was 23.

Brad Pitt and Christina Applegate

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Brad Pitt and Christina Applegate appeared together at the MTV Movie Awards in 1989.

Janet Jackson and Matthew McConaughey

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Janet Jackson and Matthew McConaughey had some romantic encounters revealed during Watch What Happens Live and nothing seems to get fans excited more than a '90s couple's reunion.

Quentin Tarantino and Sofia Coppola

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The two award-winning directors dated after Coppola separated from Spike Jonze in 2003.

Jared Leto and Cameron Diaz

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The actors 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.

Ryan Gosling and Sandra Bullock

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Ryan Gosling and Sandra Bullock dated between 2002 and 2003, when she was 38 and he was 22.

Ben Affleck and Gwyneth Paltrow

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Gwyneth Paltrow and Ben Affleck dated on and off from 1997-2000. Gwyneth later reflected on the relationship as a time she was "looking for healing" in her life.

Bradley Cooper and Renée Zellweger

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Cooper and 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.

John Mayer and Jessica Simpson

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The musicians dated in 2006. In a controversial interview in 2010, Mayer stated, "This girl was like cocaine to me."

Robert Downey Jr. and Sarah Jessica Parker

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SJP and RDJ 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.

Ryan Reynolds and Alanis Morissette

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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.

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