Who Has Winona Ryder Dated? See Her Star-Studded Roster of Exes

Winona and Rob were rumored to have dated in the mid-'80s. They starred together in the 1987 film Square Dance and attended the Golden Globes together the following year.

Winona and her Heathers costar reportedly struck up a romance between 1988 and 1989, while working on the cult classic.

Winona hooked up with her Edward Scissorhands costar Johnny Depp in the late '80s. Things got serious fast, and the two got engaged in 1990. Johnny got inked with his infamous "Winona Forever" tattoo, which he tweaked to read "Wino Forever" after they broke up in 1993. Winona has since called the split her "first heartbreak."

After her split from Johnny, Winona hooked up with Soul Asylum frontman David Pirner. They separated in 1996.

For a brief time in 1996, Winona was linked to The X-Files star.

Matt and Winona were introduced in late 1997 by none other than Gwyneth Paltrow, who at the time was good friends with Winona and also dating Matt's BFF, Ben Affleck. Winona and Matt hit it off and started a relationship, and she accompanied him to the Golden Globes in 2000, where he was nominated for his work in The Talented Mr. Ripley alongside Gwyneth Paltrow. They broke up later that year, but Winona had only good things to say about her ex in 2009. "Matt couldn't be a greater, nicer guy," she told Blackbook magazine. "I'm really lucky that I'm on good terms with him."

Though the rocker never officially confirmed his romance with Winona, the two were rumored to be an item for a short time in 2000.

In 2001, Winona had a brief relationship with singer-songwriter Pete Yorn.

Winona dated the Helmet frontman for about a year in 2003. Many of the songs and lyrics on the band's 2004 album Size Matters were inspired by her.

Winona dated filmmaker Henry Alex-Rubin in 2006. The two met while working on Girl, Interrupted in the '90s, Henry even made a mockumentary about Winona's infamous 2001 shoplifting scandal — which she starred in!

Winona dated the Rilo Kiley guitarist from 2007 to 2008. While there were rumors that they got engaged, the two never confirmed or denied it.

Rumors of a romance between Winona and the MTV funnyman were ignited after the two were spotted going on a date in 2008.

Winona was also rumored to have hooked up with British model James Gooding in 2008.

Winona has been dating fashion designer Scott Mackinlay Hahn since 2011, and the two have walked the red carpet together at many high-profile events. In a 2016 interview with The Edit, Winona opened up about why she's never been married. "I'm a serial monogamist," she said. "I'd rather never have been married than been divorced a few times. Not that there's anything wrong with divorce, but I don't think I could do it if that was a possibility. When your parents are madly in love for 45 years, your standards are really high. But I've been happily with someone for quite a while now."