Quote: "Our relationship is different than any one I've ever had. David Duchovny (55)Period: 1996Backstory: There's nothing to it, it was a fling, although they insist they were just friends. Quote: On the Howard Stern show, Grohl called Winona "a classy lady."Trivia: Their relationship is referenced in the Veruca Salt song Disconnected: "It's kind of scary when your lover leaves you for a movie star."Matt Damon (45)Period: 1997-2000Backstory: The pair were introduced by Ryder's now-former friend Gwyneth Paltrow, who at the time was Damon's BFF's Ben Affleck's girlfriend. They dated for three years and the breakup was, in Matt's words, "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." So no drama, it just ended. I'm really lucky that I'm on good terms with him."Trivia: Since their relationship was hounded by rumors of cheating on both sides, Matt was quick to deny reports he was dating co-star Penelope Cruz soon after he and Winona broke up.
“It’s so important to have a life outside the industry, to not look to it to validate you as a human being…
I’d been listening to the people I was working with – 'You should be doing this, you have to keep working or people will forget you and you won’t be relevant…’ – but my heart wasn’t in it.”Ryder calls her time off from Hollywood “an awakening.” Now, she only takes on projects she is passionate about, and actually embraces aging.“I love getting older,” she stresses. But I don’t see it as a bad thing – it can be just as interesting, if not more so, than the leading-lady, ingénue phase.”Despite the explosion of social media since Ryder’s time away from Hollywood, the star remains just as private as ever, and says she doesn’t go out much.
Sure we might want to leave the 90’s behind — things like dark lipliner, Day Glo, and a single unhooked strap of our overalls never really worked in the first place. She took her top off everywhere like it was Spring Break Cancun.
But we learned from those mistakes (and burned the tiny, sticky Polaroids), which is why it’s as good a time as any to take a look at celebrity couples of the 90’s you probably forgot about. They dated in the late 90’s but broke off their engagement by the time of the early 2000’s.
While the verdict on what is true and what is not is still awaited, let’s take a look at the timeline of his past relationships which include some of the most beautiful women in the showbiz.
Johnny Depp fell in love for the third time when he proposed his ‘Edward Scissorhands’ co-star Winona Ryder in 1990.Madonna's four-year marriage to Sean Penn was one of the wildest rides of the '80s, and that's saying something, but we agree with her words after their divorce in 1989: "I do believe we all have soul mates," she told People magazine. Ryder, 44, was previously engaged to Johnny Depp in 1990, and also dated Matt Damon in 1998, before they split two years later.“I’m a serial monogamist,” Ryder says. When your parents are madly in love for 45 years, your standards are really high.A reporter for Sassy once asked some alternative rockers if they would go out with her, explaining, "It's my theory that boys start bands so they can get famous enough to attract Winona Ryder." Courtney Love once said, "You're no one in music until you have feuded with me or until you sleep with Winona." In short, Winona had her share of fun. Quote: “We went out for two weeks and he broke my heart, or I thought he did at the time.” (Slater maintains he has no idea what she's talking about)Trivia: Slater continues to think highly of Winona, telling a journalist a couple of years ago he doesn't understand the "she's crazy" party line and that he still loved her. I like Natalie Portman."Trivia: Oberst maintains they were just friends. Jamiroquai/Jay Kay (45)Period: 2003Backstory: The musician from that video that tripped everyone out in the 90s had a fling with Winona and no one would've known about it had he not brought it up years later in a gross, dickhead way.For this one, I decided to focus on select and notable flames, trying to avoid hearsay. As always, ALL OF THIS IS FROM ARTICLES, SOURCES AND BOOKS. Johnny Depp (52)Period: 1989-93Backstory: The two met at the premiere of Great Balls of Fire! He proposed in 1990 and were engaged for three years before breaking up, allegedly because her father thought she was too young to be wed. Quote: "That was quite a while ago [...] She was very nice and trim down there. She did have this habit of wanting to constantly play hide the sausage.The ones above are the most prominent ones that Depp dated.