Movies like Play the Game

Crazy, Stupid, Love. offers a multi-generational look at relationships, featuring a cast that delivers both laughs and poignant moments. Like Play the Game, it combines humor with romantic entanglements and showcases the complexities of love at different stages of life.

Jack Nicholson plays an obsessive-compulsive writer whose life is turned upside down when he begins to care for his neighbor's dog and befriends a waitress. As Good as It Gets, like Play the Game, mixes humor with genuine character development in the realm of unexpected romance.

This film stars Jack Nicholson and Diane Keaton in a mature romantic comedy where an aging playboy finally meets his match. Like Play the Game, Something's Gotta Give appeals to those who enjoy stories about love's second chances and unexpected twists.

Grumpy Old Men explores the rivalry between two aging neighbors as they vie for the affection of a new female neighbor. This movie's blend of comedy, romance, and the depiction of older characters finding love is in a similar vein to Play the Game.

In Hitch, Will Smith stars as a smooth-talking date doctor who helps men woo the women of their dreams, but finds himself stumbling when he meets his own match. Fans of Play the Game's clever romantic maneuvers and comedic elements will surely appreciate the humor and heart in Hitch.

The Ugly Truth is a battle-of-the-sexes comedy where a chauvinistic TV host and a romantically challenged producer test theories on love, leading to unexpected results. Its use of humor to explore dating strategies and the nature of attraction makes it resonate with the tone of Play the Game.

Matthew McConaughey plays a 35-year-old who still lives with his parents and shows no signs of moving out, until they hire a professional to intervene. Failure to Launch shares Play the Game's comedic take on relationship dynamics and the journey to maturity.

Must Love Dogs tells the story of a divorcee who is pushed into trying online dating with comical results. It shares the theme of navigating love later in life with a comedic twist, which fans of Play the Game are likely to enjoy.