The emergence of ’90s and early-aughts nostalgia on Instagram has led to a modern-day 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 Brad Pitt once dated Christina Applegate; that, before Ben, Jennifer Garner was wed to one Scott Foley. Please join us as we dive down this addictive rabbit hole and rehash the celebrity couples you forgot about or never knew existed.
Photo: Shutterstock1/17Tom 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. “It was pretty hot and heavy for a little minute,” Cher said on WWHL in 2013, adding that Cruise remains “in the top five” of her best lovers.
Photo: JUKI2/17Bradley 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 Images3/17Julia Roberts and Matthew Perry
The two met when Roberts cameoed (as “Susie Underpants”) on season two of Friends in 1996. They dated for a minute, but a friend of Roberts’s told People it was “casual.”
Photo: Getty Images4/17Jennifer Garner and Scott Foley
Felicity fans know that Garner guest-starred as Foley’s (Noel’s!) girlfriend, Hannah, leading to their wedding 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 Images5/17Ryan Reynolds and Alanis Morissette
Photo: Getty Images6/17Justin 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 Images7/17Janet 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 Images8/17Sofia Coppola and Quentin Tarantino
The directors dated for two years, following Coppola’s divorce from Spike Jonze in 2003. They remain friends, with Tarantino reportedly tearing up while presenting Coppola with the Cannes Golden Lion award for Somewhere in 2010.
Photo: Getty Images9/17Brad Pitt and Christina Applegate
Flash back to 1989, when Applegate went to the MTV Movie Awards with Pitt. Applegate confirmed the story but said the two never dated again.
Photo: Getty Images10/17Cameron 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 Images11/17Jennifer 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 Images12/17Elisabeth 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 Images13/17Taylor 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 Images14/17John 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 his highly controversial 2010 Playboy interview of dating Simpson for almost a year in 2006.
Photo: Getty Images15/17Ryan Gosling and Sandra Bullock
For Notebook fans, it’s difficult to acknowledge Gosling’s romantic life outside of Rachel McAdams. But in fact he 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.
Photo: Getty Images16/17Jennifer Aniston and Adam Duritz
17/17Rihanna and Shia LaBeouf
Rihanna has long kept her love life personal, but the actor talked about their lone 2007 date with Playboy two years later, implying she 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.”
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