Who: Oscar-nominated and Golden Globe-winning actress Winona Ryder, 47, and Oscar-winning screenplay writer, actor, and producer Matt Damon, 48.
How They Met: Legend has it, Ryder’s then-bestie Gwyneth Paltrow (who was then dating Damon’s bestie, Ben Affleck), introduced the pair in December of 1997. Though the timeline isn’t concrete, this would put Paltrow’s intro during Damon’s relationship with Good Will Hunting co-star Minnie Driver.
Regardless, the early months of Damon and Ryder’s relationship couldn’t have been comfortable. Damon revealed that he was single during an interview with Oprah in the beginning of ’98 — apparently, this came as news to Driver, who then went on a press tour of sorts discussing their ill-timed breakup. Meanwhile, Damon was enjoying the awards circuit alongside Ryder.
Why We Loved Them: For a pairing of two A-listers, Damon and Ryder’s relationship slipped by surprisingly under the radar. Their commitment to keeping any personal drama out of the press was truly impressive, especially considering both parties’ romantic history (with Driver and Johnny "Wino Forever" Depp, respectively).
When They Peaked: These two peaked years after they were actually together. In 2004, Damon shared how he felt concerning the press’s treatment of Ryder following her 2001 shoplifting incident, telling Playboy, “When she was being pilloried in the press, to me it was like, ‘This too shall pass’ — that somehow her true colors would come out and she would get past it because she’s a great woman.” After comparing the blowback to Affleck’s J.Lo-era dealings with the media, he went on, “That part sucks, seeing somebody you care about being treated poorly in public.”
Ryder, too, had kind words for her ex, telling Black Book in 2009, “Matt couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him.”
The Breakup: After two years together, Damon and Ryder went their separate ways in the spring of 2000. Rumors of a romance with Damon’s All the Pretty Horses co-star Penelope Cruz circulated, but were never substantiated.
In that same aforementioned Playboy interview, Damon explained that he and Ryder had a “great relationship,” and without divulging the true reason behind their split, said, “it ended for reasons far more pedestrian than, say, a mad orgy at the Four Seasons during which my feelings were hurt because Richard Gere was too interested in her.” (For context, she played Gere’s love interest in Autumn in New York, which shot while she and Damon were still together in 1999.)
The guiding force of their breakup was perhaps more realistically Damon’s interest in dating “civilians” (his words). “These days I definitely only date, as we say, ‘civilians,'" he told Sydney's Sunday Magazine in 2004. In the beginning of his relationship with current wife Luciana Barroso, he told Playboy, “I don’t think I could fall in love with a celebrity right now, because it would mean changing my lifestyle, and I like that my lifestyle feels normal to me most of the time.”
Where They Are Now: Damon wed Barroso, his “civilian” wife, in 2005. They share four daughters together, aged 8 to 20, including Barroso’s eldest from a previous relationship. The pair will celebrate 14 years of marriage this December, and remain adorable as ever together.
Next up for Damon is the ‘60s-set Ford v Ferrari alongside Christian Bale and Caitriona Balfe.
As for Ryder, she’s been quietly dating Scott Mackinlay Hahn (the founder of eco-friendly clothing line Loomstate) since 2010. They are also undeniably adorable together.
Ryder’s hit Netflix series Stranger Things is back for its third installment on July 4.