Did we ever find out if Winona Ryder's breasts were real? I'd vote no, but she is Jewish and from my experiences at Cornell, never underestimate the power of a Jewish woman to have curves no matter how small she is. I will tip my hat to her for pulling off the short hair look. That's a tough look for many women, yet she wears it well. Even the very short hair look like in Reality Bites**. Few women pull it off well, in Hollywood: Winona, Gwyneth Paltrow and Cynthia Daniel.
There was a period of several years where every nerd loved Winona Ryder. I think it was because she did all of those Indie flicks or small budget movies. Edward Scissorhands might be the movie that sold nerds on her being cool, and then nerds saw her in Reality Bites and flipped their lids. Maybe her roles blinded nerds into thinking she dug nerdy things. There's always this nerd fantasy that they will find a hot chick who will want to discuss "orcs vs. golbins from lord of the rings", "who would win a fight: Dilbert or Drew Carey" or the "politics of the post-Battle of Endor Star Wars galaxy". It's not going to happen. I'll probably write about this later, but this is a sub-category of the men who fantasize about capturing a woman and holding her at their place for months to then form a love bond with her (weird, I know). She is an actress, a Hollywood product, and an Adam Sandler costar. I have a feeling she would not be into nerd conversations. I think her conversations are full of "yeah", "totally", "like" and "ummm". I also think she is or was a 3 girl: 3 drinks or 3 compliments and you would be fine. I would not have dated her in college because she was not evil enough.
**One time I broke up with this girl, and I told her she was straight out of Reality Bites. Like 2 days later I was hanging out with a mutual friend, explaining the breakup, and the mutual friend called my ex. My ex had Reality Bites on DVD during the call. Yeah, no mental issues there that I could say she was out of a movie and then she'd go watch the movie to investigate my observation out of insecurity.