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

Throwing shade! During a caller mag question and reply to beforehand nan last play of Stranger Things and nan upcoming Beetlejuice sequel, Winona Ryder dished connected her romanticist past, revealing that successful her 30s, she had 2 “disastrous relationships” pinch men who did her dirty. “When I look back, I’m like, ‘What nan hellhole was I thinking?’” she said. “I was making love nan type of  personification who only lets you cognize a fewer weeks successful that they’re successful a relationship pinch personification else. And you’re conscionable like, ‘What nan f–k?’”Winona, 52, has been pinch her longtime partner Scott Mackinlay Hahn, 53, for 14 years, but earlier gathering nan manner designer successful 2010, her romances included actors Rob Lowe, Christian Slater, Johnny Depp, Matt Damon and musicians Dave Pirner and Beck. “Guys people flocked to Winona,” a root exclusively tells Life & Style, “but she wasn’t ever wise to their wicked ways, and astir apt trusted group without really knowing them.”

Storied Love Life

Winona calls herself a “serial monogamist” and admits she fell difficult and accelerated erstwhile she was young. “When I was 15, location was a feline I liked, and we made out, and I thought that meant he was my boyfriend,” she revealed. “My mom had to explicate it to me.” Later, costars won her heart. “It was easy for Winona to meet guys because she was moving truthful much,” says nan source. “She’d meet them connected movie sets aliases astatine parties and premieres.” She was linked to Rob Lowe, her costar successful 1987’s Square Dance (they attended nan Golden Globes together successful 1988) past moved connected pinch her Heathers onscreen beau, Christian Slater, though she admits nan quality of their narration was ne'er 100 percent clear. “I retrieve erstwhile we were connected nan [publicity] tour, he told nan assemblage we were getting married, which sent maine into this giggling thing,” she recalled successful 2014. “I was ever thinking, ‘What’s going on? Like are we …?’ And he ne'er really answered me.”

She was distraught erstwhile her four-year romance pinch Johnny Depp ended successful 1993. “[It was] a fiercely heavy emotion … first emotion is for illustration that isn’t it?” she said. (The Edward Scissorhands costars exchanged rings aft conscionable 5 months.) “I was very depressed aft breaking disconnected my engagement pinch Johnny,” she said, adding, “I was embarrassingly melodramatic astatine nan time, but you person to retrieve I was only 19 years old.”

After making love Soul Asylum’s Dave Pirner for 2 years and a little fling pinch David Duchovny, Winona embarked connected a three-year romance pinch Matt Damon. They were introduced by communal pal Gwyneth Paltrow, who was dating Ben Affleck astatine nan time. (Matt’s ex Minnie Driver has said she was “devastated” erstwhile Matt showed up to nan 1998 Oscars pinch Winona astatine his broadside weeks aft their split.)

During nan decade successful mobility — Winona’s 30s — she had relationships pinch Beck (“I hung retired pinch her for a period aliases two,” nan “Losers” vocalist said successful 2002), Helmet vocalist Page Hamilton (they were together for little than a twelvemonth successful 2003), filmmaker Henry-Alex Rubin (they dated concisely successful 2006) and Rilo Kiley guitarist Blake Sennett (from 2007 to 2008). “I’m a hopeless romantic,” she’s said. Adds nan source, “Winona has learned astir emotion nan difficult way, but she hasn’t fto it taint her outlook connected life.

Mr. Right

She recovered her Prince Charming successful Scott. “He’s truthful great. He really is,” she says of nan cofounder of nan integrated fabric institution Loomstate, who she met astatine a premiere for her movie Black Swan. “This is her longest relationship, and possibly nan first grown-up 1 she’s had,” adds nan source, noting that “it helps that Scott isn’t an character aliases a producer. He’s not affiliated pinch nan Hollywood instrumentality astatine all, which she likes.” Those adjacent to nan character are thrilled she’s yet recovered a bully guy. “He’s had a calming effect connected Winona,” says nan source. “They person a nice, cozy life together distant from nan spotlight. Her friends person ne'er seen her happier.”