Playing by Heart is a romantic comedy-drama film that follows the lives of several characters living in Los Angeles as they navigate love, relationships, and personal growth. The film features an ensemble cast, including Hugh, an unhappily married man who tells lies to women he meets in bars; Hannah and Paul, a couple celebrating their 40th anniversary despite Paul's terminal brain tumor; Meredith, a theatre director who is hesitant to date; Gracie and Roger, a couple in a sex-only relationship; and Mark, a man dying of AIDS who reconnects with his estranged mother. The film explores themes of love, family, friendship, and the complexities of human relationships. Through a series of interconnected events, the characters' lives intersect and their relationships deepen, revealing the joys and challenges of love in all its forms. Playing by Heart is a heartwarming and engaging film that will make you laugh, cry, and reflect on the true meaning of love.

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Some movies that have similar genres and were produced around the same time as Playing by Heart include Serendipity, 10 Things I Hate About You, As Good as It Gets, Forrest Gump, Blast from the Past, What a Girl Wants.

Playing by Heart was released in theaters on January 22, 1999.