Tragic Details About Winona Ryder's Past Relationships

Winona Ryder has been in the spotlight for decades now, whether it be for her excellent performances in beloved films or her tragic personal life. At the height of the release of her film "Beetlejuice Beetlejuice," Ryder opened up further about her love life, highlighting details regarding her more than three-year relationship with fellow actor Johnny Depp. While speaking with Harper's Bazaar in July 2024, Ryder referred to her breakup with Depp in 1993 as her real-life "'Girl, Interrupted," referring to the 1999 drama in which the "Stranger Things" actor starred opposite Angelina Jolie as a woman who had been committed to a mental institution.

Depp, who starred opposite Ryder in Tim Burton's early '90s classic "Edward Scissorhands," proposed to Ryder after five months of dating, but the two never married. While her relationship with Depp played out publicly, Ryder has also been in several other relationships with famous actors, including Matt Damon. Ryder is now dating business owner Scott Mackinlay Hahn and has been since 2011. While she may be happily coupled in the present, Ryder has gone through some tough times relationship-wise in the past.

During Winona Ryder's exclusive conversation with Harper's Bazaar, the prolific actor explained that she had several difficult experiences while dating in her youth. While discussing two past relationships in particular, Ryder said, "In my 30s, I had two disastrous relationships that were—they weren't wrong, but this was before you would ever think to Google someone." It has not been confirmed who the two people she was referring to are, but it's easy to speculate these exes of Ryder's are probably famous. In the same interview, Ryder went on to recall that, at the time, she thought to herself, "What the hell was I thinking?" Ryder also detailed dating someone who was already in a prior relationship and failed to notify her of that beforehand.

Ryder referred to her breakup with Johnny Depp as her "first real heartbreak" while speaking to Elle back in 2009, and in 1993, Depp told the Los Angeles Times he partly blamed the media frenzy around them for his and Ryder's relationship failing. Ryder still seems to think highly of Depp despite their seemingly harsh breakup. After Depp was accused of abuse by his former wife, Amber Heard, Ryder released a witness statement, which partly read, "The idea that he is an incredibly violent person is the farthest thing from the Johnny I knew and loved."

Oddly enough, not all of Winona Ryder's public relationships were confirmed. While she was linked to both Christian Slater and David Duchovny, Ryder never officially confirmed either relationship. Similarly, dating rumors sparked between Ryder and Rob Lowe when the two attended the 1988 Golden Globes together, but alas, neither ever declared each other as the other's partner. There is also some debate about whether Ryder ever dated Charlie Sheen, which would presumably have been a wild ride. 

Ryder dated Matt Damon for two years in the late '90s, and the high-profile status of both actors may be the reason for their breakup since Damon told Sydney's Sunday Magazine (via Today) in 2004 he would prefer to only date civilians. If the tabloidization of Ryder and Damon's relationship was the reason for it ending, then this would seem to be a possible theme in Ryder's love life. With that said, Ryder might have had some rough experiences while dating in the past, but now, she seems to be in a happy and healthy long-term relationship, though she has still never gotten married.