21. Winona Ryder and Matt Damon tried their best to keep two year relationship out of the public eye. “My most recent relationships have not been with famous women, but I was with a very famous woman, Winona Ryder, for a couple of years, and we had a great relationship,” Damon said.
22. Ryan Reynolds and Alanis Morissette met at Drew Barrymore’s party in 2002. They dated for two years, getting engaged in 2004. The engagement never made it to marriage, as the couple broke up by 2007.
23. This one’s a bit shocking: Natalie Portman dated Moby back in 2001. When asked about the relationship, Mod: “I guess in some people’s eyes, [nerds] might be mildly sexy – and, as a nerd, I’m certainly happy to enjoy some of the effects of that.”
24. Kiefer Sutherland and Julia Roberts met on their film The Flatliners in 1990, and got together shortly after. They were engaged that year and planned to get married in the next. However, Roberts broke off the wedding just days before when she found out Sutherland had an affair with a stripper.
25. Before their acting careers took off, Juliette Lewis and Brad Pitt dated for a couple of years. From 1990 to 1993, the couple enjoyed each other’s company but once they both got those breakthrough roles, the relationship fell apart. “It was such a lovely time in my life because we were just unknown young actors in L.A,” Lewis said about the relationship.