10. Winona Ryder
Photo: etonline
When you look at the list of Hollywood’s leading men that have dated Winona Ryder over the years, it’s hard to believe one of them didn’t end up at the altar. She did come close in the 90s when she was engaged to Johnny Depp, but alas it didn’t work out. Nor did it with Val Kilmer, Matt Damon, or Keanu Reeves. Just last year, she told reporters that she wasn’t sure getting hitched would be worth the risk. She also said “I’d rather never have been married than been divorced a few times,” which is a valid argument, at least to some degree. However, isn’t there a famous quote by Alfred Lord Tennyson that says “Tis better to have loved and lost than never to have loved at all?” Although, that implies that if you’re not married you haven’t loved, which we all know is a bunch of malarkey.