Play by Heart is a fairly entertaining and unconventional romantic comedy. The film follows several people throughout L.A., and the various kinds and stages of relationships that they're in. The cast is surprisingly good and includes Angelina Jolie, Ryan Phillippe, Gillian Anderson, Madeleine Stowe, and Sean Connery. The story is well written for the most part and has some interesting things to say about people and relationships. However, it takes on a few too many characters and forces itself a bit. While it has some issues, Play by Heart is a unique and entertaining film that has a good message.