Winona Ryder Reflects On Past ‘Disastrous’ Relationships: ‘What The Hell Was I Thinking?’

“When I look back, I’m like, ‘What the hell was I thinking?’ ” she said.

Sometimes, even in your 30s, you still need to make some questionable mistakes.

Winona Ryder, 52, has had her fair share of star-studded affairs over her long career, but according to her interview for Harper’s BAZAAR August 2024 Performance Issue, she doesn’t look back on all of them fondly.

“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,” she said.

“When I look back, I’m like, ‘What the hell was I thinking?’ 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 fuck?’ ”

She didn’t acknowledge which relationships she was referring to, but Ryder was previously engaged to Johnny Depp, who she was with from 1990 to 1993. She also previously dated Matt Damon, Rilo Kiley guitarist Blake Sennett, and Helmet singer Page Hamilton.

The Reality Bites star only mentioned her more juvenile romances after talking about her iconic character that is being revived for the upcoming movie Beetlejuice, Beetlejuice. 

Lydia Deetz, once the teen daughter who could see ghosts in the original 1988 film, has now become a pill-popping widow. She’s dating—but not in love with—her obsequiously slimy manager, Rory (played by Justin Theroux). And her teenage daughter Astrid (played by Jenna Ortega) states, “My mom is a very broken person.”

Parts of Lydia reminded Ryder of a younger version of herself. She stated that while reading through her past diary accounts from her 30s, it was apparent she was struggling. “You clearly write when you’re depressed or upset. I tend to not write when I’m really happy,” she said.

“I was going through them and just asking myself, ‘How?’ I was clearly trying to deal with …” Ryder trailed off. “It was very sad. I was clearly trying to believe the best and to give grace to myself. But I was taking care of everything but myself.”

Although looking back on your life can be hard for a number of reasons, Ryder seems content with her love life now, having been in a relationship with her partner, 53-year-old Scott Mackinlay Hahn, since 2011.

“He’s so great. He really is. I’m really lucky,” she explained.