Winona Ryder and Matt Damon
Winona Ryder and Matt Damon were one of many 1980s teen loves, and while Winona went on to have high-profile, tormented romances with the likes of Johnny Depp (who even, regrettably, tattooed "Winona Forever" on his arm) Damon went on to settle down with Luciana Barroso and raise a family.
Helen Mirren and Liam Neeson
Dame Helen Mirren had quite a lengthy relationship with actor Liam Neeson, before Neeson met and married Natasha Richardson (to whom he was wed until her death in 2009).
Kim Kardashian and Nick Cannon
Kim Kardashian and Nick Cannon were once an it-couple, but nowadays Cannon hesitates to discuss the relationship: “I always get in trouble when I talk about this,” he sheepishly told the Daily Mail
Ben Affleck and Gwyneth Paltrow
Before Jennifer Garner and Chris Martin, Gwyneth Paltrow hooked up with Ben Affleck. Both actors have, as mentioned, gone on to marry other big names in the entertainment industry as well as raise families in the limelight.
Nicolas Cage and Patricia Arquette
They both went on to be big name stars, but once upon a time Nicolas Cage and Patricia Arquette were just two vaguely camera shy actors showing up to an event together, holding hands and inciting rumors about their relationship.
Meryl Streep and John Cazale
While filming “The Deer Hunter”, actor John Cazale was dying of cancer. He’d been living with his co-star, the ingenue Meryl Streep who had taken the world by storm. When doing Shakespeare in the Park in the early ‘70s, Cazale told fellow thespian Al Pacino that he’d “met the greatest actress in the world” when he first laid eyes on Streep.
Jessica Simpson and John Mayer
You probably remember when Jessica Simpson was shacking up with Nick Lachey, but how about her tryst with John Mayer?
Robert Downey Jr. and Sarah Jessica Parker
Maybe they got together since they both go by three names, but once upon a time roustabout Robert Downey Jr. was linked to Sex and the City’s Sarah Jessica Parker.
Kate Moss and Johnny Depp
A slightly odd pairing, supermodel Kate Moss was once linked to Tim Burton’s muse, the one and only Johnny Depp.
Brad Pitt and Thandie Newton
Before he was one half of Brangelina, Brad Pitt was in a relationship with English actress Thandie Newton.
Britney Spears and Justin Timberlake
Any ‘90s kid remembers “Britney + Justin Forever”, which as we now know was not anywhere near close to forever.
Cher and Val Kilmer
Even though she was 14 years older, Cher dated Val Kilmer during her heydey in the ‘80s.
Sean Penn and Elizabeth McGovern
Before she fled LA for London to star in “Downton Abbey” and he married Robin Wright, Sean Penn and Elizabeth McGovern were engaged after filming “Racing the Moon” together in the 1980s. When the engagement broke off, McGovern said that they were just too young to consider marriage. She was 22 at the time.
Jack Nicholson and Anjelica Huston
Imagine Morticia Addams dating the Joker, and that kind of sums up the tumultuous relationship
between Jack Nicholson and Anjelica Huston which lasted for 17 years.
Dennis Quaid and Meg Ryan
Two glamorous ‘80s stars who went on to the kind-of forgotten, Dennis Quaid and Meg Ryan had a bit of a fling during the height of their film careers.
Gary Oldman and Isabella Rossellini
Gary Oldman and Isabella Rossellini were once romantically linked, and in fact, they were at one point engaged to be married. Oldman eventually went on to marry Alexandra Edenborough, an English jazz singer.
Mick and Bianca Jagger
They may have only been married for eight years, but based on their amazing wedding photos, one would hope that Mick and Bianca Jagger had this much fun at least a few more times over the course of their marriage.
Sarah Paulson and Cherry Jones
Sarah Paulson’s relationship with Cherry Jones may not have been forever, but both actresses say they’ve remained friends. Jones, who is twenty-some years Paulson’s senior, is a two-time Tony Award winner.
Geena Davis and Jeff Goldblum
Geena Davis and Jeff Goldblum were not just dating, but for a time married. They also appeared in several films together, including The Fly. They divorced after Davis finished Thelma and Louise, and shirtless Brad Pitt may have made that break-up easier to endure.
Mikhail Baryshnikov and Jessica Lange
Before Jessica Lange was the Supreme, she was hooking up with world famous ballet dancer Mikhail Baryshnikov, and they actually had a (gorgeous) child
together: a daughter named Shura. Lange went on to have relations and children with Sam Shepard.
Fiona Apple and David Blaine
Crooner Fiona Apple once dated bad boy magician David Blaine. Her music would actually make a pretty decent soundtrack for his illusionist shows.
Eddie Murphy and Lisa Figeroa
Funny man Eddie Murphy dated Lisa Figueroa for much of the 1980s, and even though they eventually split, he once told a reporter
that she was ‘great for him’ because of her independent nature, adding “If a woman lets me dominate her, I get bored real fast."