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 ...

Damon and Ryder were first introduced in 1997 by Gwyneth Paltrow, who, at the time, was good friends with Winona and was also dating Matt’s BFF, Ben Affleck.

Amy Odell’s biography alleged that Winona Ryder and her then-boyfriend, Matt Damon argued. When she came back to her and ...

Both easy on the eye and regarded as two of the biggest talents of their generation, Matt Damon and Winona Ryder seemed like a match made in Hollywood heaven. While their relationship wasn’t as ...

Gwyneth Paltrow’s alleged nasty nickname for Winona Ryder was revealed in Amy Odell’s bombshell new biography about the Goop ...

Winona Ryder and Gwyneth Paltrow were once considered one of Hollywood’s coolest friendships during the 1990s. But by the ...

Damon had a couple of public relationships with his fellow actors in the past. Perhaps his most known relationships at the time were with Winona Ryder and Minnie Driver.

Gwyneth Paltrow’s is no stranger to controversy, and in her latest one yet, the Goop founder’s derogatory nickname for her ...

Gwyneth Paltrow allegedly had a rather sharp nickname for her former friend and “Stranger Things” actor Winona Ryder. Author ...

Michael Keaton, Winona Ryder in “Beetlejuice.” ©Warner Bros/Courtesy Everett Collection In her late teens and 20s, Ryder dated Rob Lowe, Johnny Depp, Dave Pirner, David Duchovny and Matt Damon.

Winona Ryder and Gwyneth Paltrow were once considered one of Hollywood’s coolest friendships during the 1990s. But by the ...