Winona Ryder’s Dating History Filled With ‘Disastrous Relationships’: ‘She Wasn’t Always Wise’

Throwing shade! During a recent magazine interview to promote the final season of Stranger Things and the upcoming Beetlejuice sequel , Winona Ryder dished on her romantic past, revealing that in her 30s, she had two “disastrous relationships” with men who did her dirty. “When I look back, I’m like, ‘What the hell was I thinking?’” she said. “I was dating the type of  person who only lets you know a few weeks in that they’re in a relationship with someone else. And you’re just like, ‘What the f–k?’”Winona, 52, has been with her longtime partner Scott Mackinlay Hahn , 53, for 14 years, but before meeting the fashion designer in 2010, her romances included actors Rob Lowe, Christian Slater, Johnny Depp, Matt Damon and musicians Dave Pirner and Beck. “Guys naturally flocked to Winona,” a source exclusively tells Life & Style , “but she wasn’t always wise to their wicked ways, and probably trusted people without really knowing them.”

Storied Love Life

Winona calls herself a “serial monogamist” and admits she fell hard and fast when she was young. “When I was 15, there was a guy I liked, and we made out, and I thought that meant he was my boyfriend,” she revealed. “My mom had to explain it to me.” Later, costars won her heart. “It was easy for Winona to meet guys because she was working so much,” says the source. “She’d meet them on film sets or at parties and premieres.” She was linked to Rob Lowe, her costar in 1987’s Square Dance (they attended the Golden Globes together in 1988) then moved on with her Heathers onscreen beau, Christian Slater, though she admits the nature of their relationship was never 100 percent clear. “I remember when we were on the [publicity] tour, he told the audience we were getting married, which sent me into this giggling thing,” she recalled in 2014. “I was always thinking, ‘What’s going on? Like are we ...?’ And he never really answered me.”

She was distraught when her four-year romance with Johnny Depp ended in 1993. “[It was] a fiercely deep love ... first love is like that isn’t it?” she said. (The Edward Scissorhands costars got engaged after just five months.) “ I was very depressed after breaking off my engagement with Johnny ,” she said, adding, “I was embarrassingly dramatic at the time, but you have to remember I was only 19 years old.”

After dating Soul Asylum’s Dave Pirner for two years and a brief fling with David Duchovny , Winona embarked on a three-year romance with Matt Damon . They were introduced by mutual pal Gwyneth Paltrow , who was dating Ben Affleck at the time. (Matt’s ex Minnie Driver has said she was “devastated” when Matt showed up to the 1998 Oscars with Winona at his side weeks after their split.)

During the decade in question — Winona’s 30s — she had relationships with Beck (“I hung out with her for a month or two,” the “Losers” singer said in 2002), Helmet singer Page Hamilton (they were together for less than a year in 2003), filmmaker Henry-Alex Rubin (they dated briefly in 2006) and Rilo Kiley guitarist Blake Sennett (from 2007 to 2008). “I’m a hopeless romantic,” she’s said. Adds the source, “ Winona has learned about love the hard way , but she hasn’t let it taint her outlook on life.

Mr. Right

She found her Prince Charming in Scott. “He’s so great. He really is,” she says of the cofounder of the organic cotton company Loomstate, who she met at a premiere for her film Black Swan. “This is her longest relationship, and maybe the first grown-up one she’s had,” adds the source, noting that “it helps that Scott isn’t an actor or a producer. He’s not affiliated with the Hollywood machine at all, which she likes.” Those close to the actress are thrilled she’s finally found a good guy. “He’s had a calming effect on Winona,” says the source. “They have a nice, cozy life together away from the spotlight. Her friends have never seen her happier.”