Movies like Playing for Keeps

Crazy, Stupid, Love. delves into various angles of love, much like Playing for Keeps. It's a comedy-drama featuring a stellar cast and weaving together multiple storylines about love, separation, and the pursuit of happiness.

Starring Jennifer Aniston and Vince Vaughn, The Break-Up showcases the complexities of relationships, mixing humor with moments of emotional truth. Audiences who appreciate Playing for Keeps for its exploration of romantic and post-marriage complexities might enjoy this.

Fever Pitch is a romantic comedy that intertwines love and sports, much like Playing for Keeps, where a commitment-phobic man juggles his love for baseball with his relationship. Fans of Playing for Keeps' blend of sports and personal relationships will find this movie charming.

Dan in Real Life shares the story of a widower who finds love unexpectedly, tying in the complexity of family dynamics and romance. It's a dramedy that captures heartwarming and quirky moments akin to those in Playing for Keeps.

Just Wright focuses on a physical therapist who falls in love with her professional basketball player client. It combines the worlds of sports and romance, making it appealing to those who enjoyed the similar thematic elements in Playing for Keeps.

Hope Springs tells the story of a middle-aged couple attempting to reconnect through intense marriage counseling. Like Playing for Keeps, it balances drama with comedy while exploring the themes of love and commitment.