Top Movies & TV Shows Similar to Playing for Keeps List

• The Lucky One - A romantic drama that features a man returning from the military and a love story that unfolds in a small town.
• The Other Woman - A romantic comedy that involves relationships, secrets, and unexpected friendships.
• Couples Retreat - A comedy about couples exploring their relationships while on vacation.
• The Break-Up - A romantic comedy focused on a couple's relationship struggles.
• She's Out of My League - A lighthearted romantic comedy about dating and self-acceptance.
• The Grown Ups - A comedy about friendships and adulthood featuring a group of childhood friends.
• Crazy, Stupid, Love - A romantic comedy surrounding love, relationships, and personal growth.
• Fever Pitch - A romantic comedy that revolves around the challenges of a relationship centered around a passion for sports.
• Hitch - A romantic comedy about love, relationships, and the challenges involved in dating.
• 50 First Dates - A romantic comedy where love has unique challenges, similar to the dynamics in Playing for Keeps.
• Wedding Crashers - A comedy focusing on relationships and social interactions during wedding gatherings.
• How to Lose a Guy in 10 Days - A romantic comedy about the challenges of dating and falling in love.
• About Time - A romantic comedy-drama featuring love and life's meaningful moments.
• The Proposal - A romantic comedy filled with misunderstandings and comedic situations surrounding love.
• The Intern - A feel-good movie about personal connections and relationships between different generations.
• The Family Stone - A comedy-drama that explores family dynamics and romantic relationships.
• Sweet Home Alabama - A romantic comedy that involves the protagonist's return to her roots and love conflict.
• 27 Dresses - A romantic comedy about commitment and love amidst personal aspirations.
• Along Came Polly - A romantic comedy about unexpected relationships and personal growth.
• Love & Other Drugs - A romantic drama-comedy about love and relationships in difficult circumstances.
• Little Black Book - A romantic comedy exploring relationships and the complications of loving someone.
• Just Go with It - A feel-good romantic comedy filled with laughter and relationship mishaps.
• The Five-Year Engagement - A romantic comedy about the challenges of being engaged and the realities of love.
• My Best Friend's Wedding - A romantic comedy that explores love and friendship dilemmas.
• Definitely, Maybe - A romantic drama about love and relationships throughout different stages of life.
• Legally Blonde - A comedy that explores self-discovery, empowerment, and personal growth.
• Knocked Up - A romantic comedy that delves into the surprises and challenges of unexpected relationships.
• Music and Lyrics - A romantic comedy that showcases an unusual love story between a washed-up pop star and a young woman.
• The Ugly Truth - A romantic comedy about the complexities of dating and relationships.
• Friends with Benefits - A romantic comedy dealing with the emotional ramifications of physical relationships.
• The Vow - A romantic drama about love enduring even through life's most challenging trials.
• Slumdog Millionaire - A unique blend of romance and social commentary on love in challenging circumstances.
• Notting Hill - A romantic comedy portraying celebrity relationships and love against all odds.
• You Again - A comedy that focuses on relationships, rivalry, and personal growth in the face of family dynamics.
• Little White Lies - A dramedy that deals with relationships and personal conflicts among friends.
• The Wedding Planner - A romantic comedy about love that develops amidst the chaos of wedding planning.
• Two Weeks Notice - A romantic comedy that explores the unexpected love that can evolve in the workplace.
• When in Rome - A romantic comedy that follows the comedic consequences of love and chance.
• P.S. I Love You - A romantic drama about love continuing beyond loss and the importance of connections.
• The Holiday - A romantic comedy that focuses on the complexities and surprises of love during holiday seasons.
• Not Another Teen Movie - A comedy that parodies teenage romance and relationships, offering humor related to love.
• To All the Boys I've Loved Before - A romantic teen comedy about love letters and unexpected relationships.