Movies like How Do You Know

The Holiday offers a similar blend of romance and life's unexpected turns. Starring Cameron Diaz and Kate Winslet as two women who swap houses for the holidays, this movie presents heartwarming growth and connections, appealing to viewers who enjoy endearing storylines and life-changing romances.

For another rom-com that mixes humor with a female protagonist's personal growth and relationship woes, Bridget Jones's Diary stands out. Renée Zellweger's portrayal of the titular character will resonate with audiences who enjoy watching relatable life struggles and romance.

Starring Anne Hathaway and Robert De Niro, The Intern showcases an unlikely friendship, personal growth, and navigating professional and private lives. With its heartwarming narrative and relatable characters, fans of How Do You Know will find The Intern a delightful watch.

This ensemble film offers multiple perspectives on love, ranging from youthful crushes to married life challenges. Crazy, Stupid, Love. is smart, heartfelt, and comedic in equal measures, making it a great choice for those charmed by How Do You Know's exploration of romantic entanglements.

Again featuring Jack Nicholson, As Good as It Gets is a film about unexpected relationships forming between flawed individuals. With sharp dialogue and a captivating blend of drama and wit, this movie is perfect for fans of the dynamics in How Do You Know.

Directed by James L. Brooks, who also directed How Do You Know, Spanglish balances the difficulties of cultural assimilation with personal and romantic relationships. This movie's blend of humor and emotional depth makes it a fitting choice for viewers who appreciate character-driven storytelling.

This charming film intertwines romance and comedy, much like How Do You Know. With a well-seasoned cast consisting of Jack Nicholson and Diane Keaton, Something's Gotta Give explores the complexities of love later in life, resonating with fans of witty and mature romantic comedies.

This is another relatable film that delves into the intricacies of romantic relationships among a more mature cast, starring Meryl Streep, Steve Martin, and Alec Baldwin. It's Complicated addresses the unique challenges of love, family, and starting over, much like How Do You Know.