Winona Ryder and Matt Damon were once an item, Kevin Mazur/WireImage.com Winona Ryder. There was a time when the actress -- who found fame as a teen star in the '80s and rode her wave of critical acclaim and big-screen success for a good 15 years -- was as well known for her relationship with fellow celeb Johnny Depp as for her movie roles (and later, her various troubles). After all, the two were engaged for three years when Winona was in her early 20s, and Johnny even inked himself with a tattoo that declared "Winona Forever" (which he later edited down to "Wino Forever" after they split). But while it seems everyone remembers that romance, most have forgotten that Winona dated another fellow celeb several years back -- an up-and-coming actor named Matt Damon.
As Winona turns 40 on October 29, omg! looks back at what once was between her and mega-star Matt.
How They Met: It was none other than Gwyneth Paltrow -- the girlfriend of Matt's BFF Ben Affleck -- who introduced the two in December 1997. Matt and Winona hit it off and starting dating shortly after (or, according to some reports, before) Matt and his "Good Will Hunting" co-star Minnie Driver broke up. However, Gwyneth and Winona, who were pals for a while, eventually had a falling out, reportedly after the perfect Miss Paltrow won a best actress Oscar in 1998 for "Shakespeare In Love" -- supposedly a part Winona was offered first.
Their Public Appearances: After Matt and Ben's "Good Will Hunting" blew up at the box office, the Beantown boys got more good news when the film was nominated for a whopping nine Oscars (the guys won for best original screenplay after winning a Golden Globe in the same category). While Matt brought his mom as his date, Winona was on his arm at Harvey Weinstein's pre-Oscar party in March of 1998, which put the relationship smack in the middle of the spotlight. From then on the couple was plagued by media reports of troubles and breakups. Nearly two years later, however, the couple was still together, smooching on the red carpet in January of 2000 at the Golden Globe Awards.
The End: Just a month after that Golden Globes appearance, the rumors finally proved true and Matt and Winona (who could have been the world's next Manona, or would it be Watt?) had called it quits. Matt moved on to a relationship with his "All the Pretty Horses" co-star Penelope Cruz.
Winona Ryder turns 40 on October 28, Stefanie Keenan/WireImage.com
Winona's Look Back: "Matt couldn't be a greater, nicer guy. I'm really lucky that I'm on good terms with him," Winona said in a 2009 interview with Black Book magazine.
Matt's Look Back: "My most recent relationships have not been with famous women, but I was with a very famous woman, Winona Ryder, for a couple of years, and we had a great relationship," Matt told Playboy four years after their breakup. "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."
Matt These Days: Matt's become one of Hollywood's biggest stars with the "Bourne" franchise and high-paying lead roles in recent big films like "Invictus," "The Adjustment Bureau," and "Contagion." Matt, now 41, chose a far from famous woman to settle down with when he married bartender Luciana Barroso in 2005. The couple has three daughters together in addition to Luciana's daughter from a previous marriage.
Winona These Days: The actress' career stalled after her highly publicized shoplifting arrest in 2001, but she made a recent comeback with a Screen Actors Guild Award nomination for her role in last year's critically acclaimed "Black Swan." On the personal front, the still-single Winona told OK! magazine earlier this year that she wants to make sure she's found Mr. Right before tying the knot. "I very much believe in marriage. I hope to only be married once, which is why I've never been married. But I am a strong believer. My parents have been together for 40 years and are still very much in love so I think I have very high standards."
And like many women approaching the big milestone, she's noticing her biological clock more and more. "Well, the weird thing is when I turned 38, I didn't really think about it, and then at 39, being a year away from 40, you sort of feel like you don't have excuses anymore!" she told the mag. "If you're a woman and you want to have children, you feel a little bit of pressure there."
Kids or not, hopefully Winona's 40s will be fabulous. Matt Damon's certainly are!