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 with short memories 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 just never knew existed.
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Val Kilmer and Cher
Cher lovingly called Kilmer a “funny, crazy, pain in the ass” in her social media tribute to the recently departed actor, whom she dated for a few years in the early 1980s. (The two went on to be great friends.)
Photo: Getty Images2/36Cameron Diaz and Matt Dillon
If you, like me, have a fairly vivid recollectsion 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.”
Photo: Getty Images3/36Madonna 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.)
Photo: Getty Images4/36Tom 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.
Photo: Getty Images5/36Julia 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.”
Photo: Getty Images6/36Keira 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 Mail on Sunday that he felt “a bit second-rate” compared to her, and that it put pressure on their relationship.
Photo: Getty Images7/36Ryan Reynolds and Alanis Morissette
Photo: Getty Images8/36Justin 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.
Photo: Getty Images9/36Jennifer 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. Garner said she and Foley “really were the victims of Hollywood.”
Photo: Getty Images10/36Sofia 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 Cannes Golden Lion award for Somewhere in 2010.
Photo: Getty Images11/36Cameron 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.
Photo: Getty Images12/36Jennifer 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 right 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.
Photo: Getty Images13/36Elisabeth 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.
Photo: Getty Images14/36Taylor 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.”
Photo: Getty Images15/36Janet 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.”
Photo: Getty Images16/36Ryan 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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Lisa 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.
Photo: Getty Images18/36Jennifer 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.
Photo: Getty Images19/36Rihanna and Shia LaBeouf
LaBeouf recalled his one and only date with RiRi in Playboy in 2009, implying that the future beauty mogul texted him and they went to dinner: “I was filming a sword fight when I got the message. I said, ‘Can this be my life?’ It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”
Photo: Getty Images20/36John Krasinski and Rashida Jones
Fans of The Office may have loved the “will they or won’t they” vibe 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.
Photo: Getty Images21/36Nick Lachey and Kim Kardashian
After calling it quits with Jessica Simpson in 2006, Lachey went on a low-key movie date with Kardashian. (Believe it or not, they saw…The Da Vinci Code.) As they left, however, there were about 25 photographers waiting outside, which Lachey suspected was Kardashian’s doing. “I think there were other things in play on our little rendezvous,” he told Andey Cohen in 2019, during an episode of Watch What Happens Live.
Photo: Getty Images22/36Mila 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.”
Photo: Getty Images23/36Bradley Cooper and Renee 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 might not remember either.
Photo: Getty Images24/36Jason 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.
Photo: Getty Images25/36John 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.
Photo: Getty Images26/36Scarlett 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.
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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.
Photo: Getty Images28/36Michelle 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.
Photo: Getty Images29/36Leighton 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.
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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.”
Photo: Getty Images31/36Jennifer Aniston and Vince Vaughn
While working on their film The Break-Up, Aniston and Vaughn started dating, finally calling it quits IRL 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.”
Photo: Getty Images32/36Liv 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.
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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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Drew 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.”
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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.
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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.
