Winona Ryder's Dating History Includes A-List Hollywood Actors and Musicians

Winona Ryder's dating history has been a pretty wild ride. When the actress rose to fame in the late 1980s, it wasn't just casting agents and directors who were interested in her. It also became crystal clear that some Hollywood stars had all eyes on her.

Winona has been rumored to be in a relationship with different celebrities; the actress said that before finding love with her current boyfriend, she didn't know how to date.

It's over ten years since she started dating her current boyfriend, who is far from the spotlight. According to the actress, she doesn't envision getting married because she fears divorce.

Rob Lowe

Winona and Rob met in the late 1980s on the set of the film "Square Dance." While on set, Winona would capture Rob's attention, and soon after, they started dating. Although their relationship progressed past the making of the film, the couple kept a low profile about their romance.

However, according to reports, their lengthy age difference might have contributed to the couple keeping their love life a secret. Rob, at the time, was 23, and Winona was just 16.

The couple made their first public appearance in 1988 at the Golden Globes ceremony. According to reports, the two only dated for a year and called it quits.

Christian Slater

Winona met Christian after her breakup with Rob. According to reports, the two were in a relationship from 1988 to 1989. They have also starred together in the 1989 cult classic "Heathers."

Johnny Depp

Johnny and Winona dated for three years before their split in June 1993. Months after their breakup, Johnny spoke about his relationship with Winona; he stated that it was a mistake for them to go public, adding that it made people feel as if they were part of it.

After their breakup, Johnny changed his "Winona forever" tattoo to "Wino forever." The actress also disclosed that she went through a difficult time after the split. Winona stated that at the time of her engagement with Johnny, she was only 19.

The actress also recalls that, after the breakup, she was drowning in depression after being diagnosed with Anticipatory Nostalgia. She was prescribed sleeping pills that she says used to sometimes take her to a dark place.

Keanu Reeves

Winona and Keanu were never together; however, they kept joking that they were married after starring in one movie together. In an interview in 2018, the actress said that her onscreen marriage ceremony with Keanu in the 1992 film "Bram Stoker's Dracula" was presided over by a real Romanian priest.

Although Scott likes to keep a low profile, he's been spotted with Winona at a few red-carpet events.

During a joint interview with Keanu, Winona stated they got married in "Dracula" and added that the wedding scene was shot on Valentine's Day. Keanu also clarified their status in an interview in November 2021. The actor confirmed that they took the marriage oath with real priests.

David Pirner

After her breakup with Johnny, Winona started dating Soul Asylum frontman David Pirner after they met at an MTV Unplugged session event in 1994. Their relationship lasted two years before they called it quits in 1996.

David Duchovny

Shortly after her breakup with Pirner, Winona started dating actor David Duchovny in 1996. According to reports, they only dated for a short while in the late 1990s.

Matt Damon

In 1997, Winona met Matt through her then-bestie, Gwyneth Paltrow. Soon after, they started dating and kept their relationship confidential. After two years together, Matt and Winona went their separate ways in the spring of 2000.

Their separation was after Matt allegedly had a romantic affair with his "All the Pretty Horses'' co-star Penelope Cruz. In an interview, Matt explained that he had a great relationship with Winona; however, he didn't disclose the reason behind their breakup.

Matt added that after his relationship with Winona, he was more interested in dating civilians. When he started dating his current wife, Luciana Barroso, the actor said he didn't envision dating a celebrity because he would have to change his lifestyle.

Even after going their separate ways, the two were still concerned about each other. In 2004, Matt raised concerns about the press treatment of Winona following her 2001 shoplifting incident.

Winona also had kind words for her ex. In an interview in 2009, the actress stated that Matt was a great guy and she was lucky to be on good terms with him.

Beck

Although Beck never officially confirmed their relationship, Winona connected with the musician briefly in 2000. During a Rolling Stone interview, Beck confirmed that he did hang out with Winona for a month or two. However, he said that talking about his relationship with Winona would be weird unless he was a complete exhibitionist.

Pete Yorn

In 2001, Winona reportedly had a romance with rock star singer and songwriter Pete Yorn; however, according to Pete's spokesman, the two were just friends. Winona's spokesman also declined to talk about the matter, stating that he wasn't in a position to comment on his client's dating life.

Page Hamilton

Winona dated American guitarist, singer, songwriter, and record producer Page for almost a year in 2003. Page, who is mainly recognized for his work as frontman of the Helmet band, wrote many songs and lyrics on the band's 2004 album "Size Matters." It is reported that Winona inspired the songs.

Henry Alex-Rubin

Henry was a filmmaker who made a mockumentary about Winona's shoplifting scandal in 2001. Reports indicate that the actress and Henry knew each other for years before they began dating but later broke up.

Blake Sennett

Blake is an American actor and musician who was the lead guitarist for Indie Rock Band Rilo Kiley. It is reported that Winona and Blake dated from 2007 to 2008 and even got engaged. However, neither of them confirmed nor denied the rumors.

Tom Green

Rumors of a romantic relationship between the Canadian-American comedian Tom and Winona began circulating after the two went on a date in 2008. Nothing was heard of the duo after that, so maybe it was a brief dating moment at the time.

Scott Mackinlay Hahn

The "Stranger Things" star and Scott have been in a relationship since 2011 but have kept private details about their love life. In recent years, Winona has occasionally opened up about her long-term relationship with Scott.

During an interview at the premiere of "Stranger Things," the actress disclosed that she was seeing someone and they were happy. Winona opened up about her previous dating life, stating that it confused her before she finally found love:

"I was single for a while and dating; I just didn't know how to do it! I've always been like that."

Although Scott likes to keep a low profile, he's been spotted with Winona at a few red-carpet events. Scott accompanied the actress during the Screen Actors Guild Awards in January 2020, wearing coordinating outfits.

In May 2022, the couple attended the New York premiere of "Stranger Things" season 4, wearing matching navy blue suits. Scott says that when they first met, he didn't know who Winona was, and he confused her for a different actress, Milla Jovovich, complimenting her on her role in the film "The Fifth Element."

The actress stated that she connected in so many ways with Scott when they met and was glad that he wasn't in showbiz. Scott and Winona are not yet married despite dating for over ten years; according to the actress, she doesn't want to be divorced.

In 2016, Winona Ryder explained in an interview that she'd rather not get married than be divorced a few times, adding that her parents have been in love for 45 years, so her standards are pretty high.