The ubiquity of 1990s and early aughts nostalgia on Instagram, TikTok, and beyond has led, in recent years, to a resurgence of bodysuits, brown lipstick, combat boots, and chokers. But yearning for the semi-recent past has also reminded those of us who might not have been around to witness it that the late, great Val Kilmer once romanced Cher; Liv Tyler once dated Joaquin Phoenix; and that before Ben, Jennifer Garner was wed to one Scott Foley.
Please join us as we dive down this frankly thrilling rabbit hole and rehash the celebrity couples you forgot about—or simply never knew existed.
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Photo: Getty Images 1/41Cindy Crawford and Richard Gere
Before Crawford’s daughter Kaia Gerber and Gere’s son Homer Gere were co-stars on FX’s The Shards (and Vogue co-cover stars), the supermodel mère and actor père were one of the great power couples of the 1990s, eloping in Las Vegas in 1991. “It was a nice Armani suit, but I didn’t dream of getting married in a navy blue suit,” Crawford has said of her impromptu bridal look.
Val Kilmer and Cher
Cher lovingly called Kilmer a “funny, crazy, pain in the ass” in her social media tribute to the actor—whom she dated for a few years in the early 1980s—after his death in 2025.
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Photo: Getty Images 3/41Cameron Diaz and Matt Dillon
If you, like me, have a fairly vivid recollection of ’90s pop-cultural ephemera, you might already remember that Diaz dated her There’s Something About Mary co-star from January 1996 to September 1998. Dillon even called Diaz his “muse” in a 2006 interview with Parade, saying: “I hadn’t been in any deep emotional relationships.”
Madonna and Tupac Shakur
Before they became two of the most influential musical artists of all time, Madonna and Tupac semi-secretly dated after attending the 1993 Soul Train Music Awards as friends. (Rosie Perez introduced them, which is perhaps the most iconic way there is to meet someone.)
Tom Cruise and Cher
Not only were Maverick and the queen of camp together, but they met at Sean Penn and Madonna’s wedding in 1985, when Cher was 39 and Cruise was 23. (Look, she has a type!)“It was pretty hot and heavy for a little minute,” Cher said on Watch What Happens Live in 2013, adding that Cruise remains “in the top five” of her best lovers.
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Photo: Getty Images 6/41Julia Roberts and Matthew Perry
The two met when Roberts made a cameo (as “Susie Underpants”) on season two of Friends in 1996. Perry discussed their tryst in his 2022 memoir, Friends, Lovers, and the Big Terrible Thing, writing, “Dating Julia Roberts had been too much for me…So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”
Keira Knightley and Jamie Dornan
Knightley and Dornan dated from 2003 to 2005, when he was still a model (and pre–Fifty Shades of Grey) and her career was flourishing. A few years after their breakup, Dornan told the British press that he felt “a bit second-rate” compared to her, and that it put pressure on their relationship.
Ryan Reynolds and Alanis Morissette
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Photo: Getty Images 9/41Justin Timberlake and Jenna Dewan
Before she was famous, Dewan was a backup dancer for the singer, who kinda-sorta-maybe dated him after his breakup from Britney Spears circa 2002. “We were, like, friends…that dated,” Dewan has confirmed.
Jennifer Garner and Scott Foley
Felicity fans know that Garner guest-starred as Foley’s (Noel’s!) girlfriend, Hannah, before they married in 2000. But they divorced in 2003, after Alias made her a star.
Sofia Coppola and Quentin Tarantino
The directors dated for two years, following Coppola’s divorce from Spike Jonze in 2003. They remained friends, with Tarantino reportedly tearing up while presenting Coppola with the Golden Lion award for Somewhere at the 2010 Venice Film Festival.
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Photo: Getty Images 12/41Cameron Diaz and Jared Leto
Behold the emo paparazzi faves, who dated from 1999 to 2004 (before she moved on to Justin Timberlake). The actor and the actor/Thirty Seconds to Mars frontman were even engaged for a time.
Jennifer Aniston and Tate Donovan
Remember the Friends story line in which Rachel (Jennifer Aniston) dates one of her personal-shopping clients, Josh (Tate Donovan)? Well, in real life, the two actors had also been dating—but as they were filming their episodes together, they were actually breaking up. “We were like, ‘Hey, can we not keep doing this? ’Cause this is really painful and tough,’” Donovan told Us Weekly about the experience.
Elisabeth Moss and Fred Armisen
The talented couple’s 10-month marriage in 2009 spawned one of the best celebrity interview quotes of all time: “One of the greatest things I heard someone say about him is, ‘He’s so great at doing impersonations. But the greatest impersonation he does is that of a normal person,’” the Handmaid’s Tale star told Page Six in 2012.
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Photo: Getty Images 15/41Taylor Swift and Taylor Lautner
The young Valentine’s Day stars dated for a few months in 2009. He was later rumored to be the inspiration for “Back to December,” which Swift has said “was about a person who was incredible to me, just perfect to me in a relationship, and I was really careless with him.”
Janet Jackson and Matthew McConaughey
On Watch What Happens Live—apparently the main place for past celebrity couples to tell all—McConaughey said the two “had dinner one night. That was sorta it.”
Ryan Gosling and Sandra Bullock
Gosling dated Bullock in 2002 and 2003, when she was 38 and he 22. They were even red-carpet official at the Cannes premiere of Murder by Numbers and the premiere of Gosling’s film The Believer.
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Photo: Getty Images 18/41Lisa Marie Presley and Nicolas Cage
You’d be forgiven for forgetting that Presley and Cage were briefly married in 2002; they separated after three months. “I’m sad about this, but we shouldn’t have been married in the first place,” Presley said through a representative at the time.
Jennifer Aniston and Adam Duritz
Aniston and the Counting Crows frontman dated in 1995 after meeting through a mutual friend. Then, in 1997, Duritz went on a date with Aniston’s best friend and costar, Courteney Cox.
John Krasinski and Rashida Jones
Fans of The Office may have loved the “will they or won’t they” thing between Krasinski and Jones onscreen, but behind the scenes, the two had actually dated for almost a year (and then broken up) before Jones came on the show. Suffice it to say, they were better as friends.
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Photo: Getty Images 21/41Mila Kunis and Macaulay Culkin
Before partnering up with Ashton Kutcher and Brenda Song, respectively, Kunis and Culkin were involved for a shockingly long time, from 2002 to about 2010. While both have stayed relatively mum about their relationship, Kunis provided some insight into their split, telling Howard Stern in 2016 that it was difficult to go out in public with the Home Alone star. “You couldn’t walk down the street with him,” she explained, noting that fans “just screamed when they saw him.”
Bradley Cooper and Renée Zellweger
Imagine the prestige awards that would have lined the mantle had Cooper and Zellweger, who dated for two years from 2009 to 2011, stayed together. The thespians met on the set of Case 39, a movie you may not remember either.
Jason Schwartzman and Zooey Deschanel
Schwartzman and Deschanel go way back: The actors first dated in 1999, when they were both just 19 years old. (Deschanel has referred to Schwartzman as her first “real boyfriend.”) After breaking up and then rekindling their romance, the two called it quits for good in 2005.
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Photo: Getty Images 24/41John Mayer and Jessica Simpson
“Yeah, that girl is like crack cocaine to me. Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm,” Mayer said in a highly controversial 2010 Playboy interview of dating Simpson for almost a year in 2006.
Scarlett Johansson and Josh Hartnett
After Johansson and Hartnett met on the set of their 2006 film The Black Dahlia, they dated for a little over a year.
Kat Dennings and Josh Groban
At the height of her 2 Broke Girls fame, Dennings and Groban were an item, making their red carpet debut as a couple at a Beverly Hills charity ball in 2014. They would remain together for two years.
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Photo: Getty Images 27/41Michelle Rodriguez and Cara Delevingne
Rodriguez and Delevingne dated for a few months in 2014, after which Delevingne entered a relationship with St. Vincent. Rodriguez reacted positively to the news of Delevingne’s new GF, telling E! News: “Oh, that’s so sexy, you go girl!” We couldn’t have said it any better.
Leighton Meester and Sebastian Stan
It’s no wonder that Meester and Stan had so much on-screen chemistry in Gossip Girl; the two met on set in 2007 (when Stan began appearing as Carter Baizen) and dated from 2008 to 2010.
Nicole Kidman and Lenny Kravitz
Not only did Kidman and Kravitz date, but they were actually engaged. Their 2003 breakup seems to have been amicable, however. “I knew Zoë because I was engaged to her father,” Kidman said during the press tour for Big Little Lies. “It’s all in the family! I love Lenny. He’s a great guy.”
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Photo: Getty Images 30/41Jennifer Aniston and Vince Vaughn
While working on their film The Break-Up, Aniston and Vaughn started dating, actually calling it quits after a year. But it wasn’t all bad; Aniston has credited Vaughn with helping her move on after her divorce from Brad Pitt in 2005. Speaking to Vogue in 2008, she said: “I call Vince my defibrillator. He literally brought me back to life… He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course.”
Liv Tyler and Joaquin Phoenix
Tyler and Phoenix showed tremendous promise as a’90s power couple between 1995 and 1998. “I fell in love with Joaquin the second I saw him,” Tyler told The Morning Call in 1997.
Ashley Olsen and Lance Armstrong
Following his split from Tory Burch (but before he took up with Sheryl Crow), Armstrong got together with Olsen in 2007. However, according to a tell-all about Armstrong, the cyclist was urged to end their relationship due to their 15-year age gap.
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Photo: Getty Images 33/41Drew Barrymore and Christian Bale
In 2012, Bale revealed to GQ that he’d gone out with Barrymore once—but she ghosted him. “We went to see some bloody awful horror film, and that was the end of it,” he said. “She never called again.” During a 2015 appearance on Watch What Happens Live, Barrymore was asked why. “I don’t know! He was so nice,” she said. “I wasn’t, like, super boy crazy. I had a lot of fish to fry, like, I had big problems in my world for many years…boys are, like, very secondary.”
Katie Holmes and Jamie Foxx
Given her proclivity for stylish solo pap walks (that is, unless she’s accompanied by her daughter Suri), it can be easy to forget that for a solid six years, Holmes and Foxx were rumored to be romantically linked. Though it remains unclear when, exactly, things started heating up, the pair were offically over by the summer of 2018.
Rachel Bilson and Bill Hader
After his divorce in 2018—but before he got together with comedian Ali Wong in the spring of 2023—Hader and Bilson were involved for a bit, attending the Golden Globes together in 2020. They would last a few months, parting ways that summer. “It was probably the hardest thing I’ve ever done, harder than childbirth,” Bilson later said of nursing her heartbreak during lockdown.
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Photo: Getty Images 36/41Amy Poehler and Nick Kroll
Kroll is now raising two children with his landscape-designer-and-artist wife, Lily Kwong, while Poehler (who shares two kids with ex-husband Will Arnett) has been dating Joel Lovell since 2024, but the two comedians were an item from 2013 to 2015. In her 2014 memoir, Yes Please, Poehler wrote of Kroll: “I have a boyfriend who knows how to settle me. He puts his hand on my chest and tells me boring stories.”
Aubrey Plaza and Michael Cera
Plaza recently welcomed her first child with now-partner Christopher Abbott, but before that, she quietly dated Cera for a year and a half after the two met on the set of Scott Pilgrim vs. the World. “We almost got married,” Plaza divulged in a 2026 episode of the SmartLess podcast. “We drove across the country together, eating a bag of edibles, and we drove to Vegas with a plan to get married and then get divorced right away so we could call each other our ex-wife and ex-husband forever. We thought that would be a really good bit.”
Sarah Paulson and Cherry Jones
Before Paulson’s long-running relationship with Holland Taylor became the stuff of age-gap lesbian dreams, she dated Jones from 2004 to 2009, with Jones describing their split as “the happiest breakup that’s ever been…we grew so much together, and now we can send each other off with a kiss and great love.”
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Photo: Getty Images 39/41January Jones and Jason Sudeikis
Long before Sudeikis’s much-publicized split from Olivia Wilde, he and Mad Men star Jones dated for about six months in 2011, with a source telling People of their breakup: “They’ve been on and off for a few months and then the long distance kind of ended it, but they could get back together. It was just hard to stay together with the distance.” The more you know!
Tyra Banks and Seal
Long before Seal’s ex-wife Heidi Klum or Banks’s current long-term partner, Canadian businessman Louis Bélanger-Martin (in case you didn’t know) entered the scene, these two stars had a brief but highly publicized relationship in 1996, as Rose’s “Kiss From a Rose” dominated the charts.
Matt Damon and Winona Ryder
No less a ’90s Hollywood golden couple than Gwyneth Paltrow and Ben Affleck introduced Damon and Ryder in late 1997, and the two dated from 1998 to 2000, rarely discussing their relationship with the press and allegedly remaining on good terms after their split.
