Christian Slater 46 Period: The two kids dated briefly while filming the iconic cult classic Heathers. She was 17, he was It didn't end well, probably due to miscommunication over how exclusive they actually were.
Slater continues to think highly of Winona, telling a journalist a couple of years ago he doesn't understand the "she's crazy" party line and that he still loved her. Johnny Depp 52 Period: The two met at the premiere of Great Balls of Fire!
He proposed in and were engaged for three years before breaking up, allegedly because her father thought she was too young to be wed. Tim Burton recalled Depp being distraught over the break up, and many fans consider the two to be soulmates. They sure were pretty together. He was my first everything.
My first real kiss. My first real boyfriend. The first guy I had sex with. So he'll always be in my heart. Kind of funny that word. Depp famously had a tattoo placed on his arm which read "Winona Forever. The two lived together and were, according to Ryder's Rolling Stone interview, very much protective of each other. It's just more casual. It's more of a friendship, really. What I'm basically saying is that it's not full of drama, which is really nice.
Winona and Pirner remain friends to this day, apparently. David Duchovny 55 Period: There's nothing to it, it was a fling, although they insist they were just friends. We'll list it anyway. I just don't like to talk about my personal life. It's an area I don't go into. He ended up leaving her for Winona, and the pairing lasted for mere months.
On the Howard Stern show, Grohl called Winona "a classy lady. Their relationship is referenced in the Veruca Salt song Disconnected: The two kept their relationship on the DL until she showed up as his date to Harvey Weinstein's pre-Oscar party. They dated for three years and the breakup was, in Matt's words, "far more pedestrian than, say, a mad orgy at the Four Seasons during which my feelings were hurt because Richard Gere was too interested in her.
I'm really lucky that I'm on good terms with him. Since their relationship was hounded by rumors of cheating on both sides, Matt was quick to deny reports he was dating co-star Penelope Cruz soon after he and Winona broke up. Pete Yorn 41 Backstory: The pair dated briefly until Winona was arrested for shoplifting in Are these pics even Pete Yorn? Why doesn't it look like him to me? Conor Oberst 35 Backstory: The two had a fling in I like Natalie Portman. Oberst maintains they were just friends.
The musician from that video that tripped everyone out in the 90s had a fling with Winona and no one would've known about it had he not brought it up years later in a gross, dickhead way. And she has these enormous breasts. She did have this habit of wanting to constantly play hide the sausage. Upon trying to sex shame Winona, Kay was promptly ridiculed by the public for being unable to keep up with Winona.
Page Hamilton 55 Backstory: The two dated quietly for a short period of time before breaking up. Many of the songs from the Helmet album Size Matters were rumored to be inspired by Hamilton's relationship with Winona. Henry Alex Rubin 39 Period: Winona met the director when he was shooting a mockumentary about her shoplifting scandal. They claim to have just been friends, showing up at several events together. The two remain friends, with Winona appearing on Rubin's instagram every so often.
Winona dated Rilo Kiley's Blake for ten months before breaking up. Winona was reportedly devastated by the break up. Winona seems to have finally settled down with fashion designer and co-creator of Loomstate, Hahn. She seems happy but unwilling to discuss her boyfriend. It's not something I'm hiding but I learned early on not to talk about that.
He's not in this industry. Dude's apparently rich and very private. Good luck to you, Winona!