Playing by Heart is a 1998 romantic dramedy directed by Willard Carroll and featuring an All-Star Cast including Gillian Anderson, Sean Connery, Angelina Jolie, Ryan Phillippe, Gena Rowlands, and Jon Stewart. The film follows a number of characters living in Los Angeles and their relationships.
- The Alcoholic: Joan seems to be edging around this. At their first meeting Keenan notices how quickly she gulps down her martini, and later comments on her drinking. She stops drinking at this point, but her parents are clearly (pleasantly) surprised by this, so it wasn't just in Keenan's head.
- Anguished Declaration of Love: Joan makes one for Keenan after he reveals he's got HIV.
- Dark Secret: Keenan avoids getting too close to Joan, until he reveals that he was infected with HIV by his last girlfriend.
- Faux Yay: Hugh attempts this at a gay bar, but the Drag Queen he's chatting to sees through the ruse.Lana: Lana may be three sheets to the preverbial wind, but I don't believe a single word coming out of your pretty, straight, little mouth.
- Fiery Redhead: Joan. Meredith has the red hair, but not the personality.
- The First Cut Is the Deepest: For Keenan, with devestating consequences.
- Happily Married: Paul and Hannah.
- Hyperlink Story: The final scenes of the film reveal how the characters are linked- Joan, Meredith and Gracie are Paul and Hannah's daughters; Hugh is Gracie's husband and Roger is the celebrant who is presiding over Paul and Hannah's renewal of their vows. A couple of scenes earlier, Mark is revealed to be Meredith's ex.
- Silly Rabbit, Romance Is for Kids!: Meredith's view of relationships- after getting hurt one too many times she's reluctant to get involved with Trent.
- Single Woman Seeks Good Man: Joan
- You Gotta Have Blue Hair: Keenan
- Your Cheating Heart: Played straight with Gracie who is cheating on Hugh with Roger who is also cheating on his spouse.
- Keenan's first girlfriend cheated on him, and consequently infected him with HIV.
- Averted with Paul, who admits to Hannah that he toyed with having an affair with a former co-star in the past, but resisted temptation.