Family & Relationships Marriage & Divorce

Top 10 Engagement and Courting Movies

By Family & Relationships Last updated Sunday, June/30/2024

Looking for a unique way to pop the question? Trying to figure out how to get him to propose? Watching these movies together may help open up dialogue between the two of you about commitment and marriage and give you tips on what not to do.

1. "While You Were Sleeping" (1995)

Alone with her cat during the Christmas holidays, Lucy (Sandra Bullock) has a fantasy romance with Peter (Peter Gallagher) who doesn't know she exists. While he is in a coma, through a strange turn of events, his family believes that she is his fiancé. Movie magic helps Lucy receive a marriage proposal from the right guy, Jack (Bill Pullman). She also gets a terrific set of in-laws.Buy from Amazon »

2. "It Happened One Night" (1934)

Heiress Ellie Andrews (Claudette Colbert) runs away when her father annuls her marriage to a playboy. As she hitchhikes through the countryside, she finds herself and sexy, manly, endearing Peter Warren (Clark Gable). Sure, he is a reporter looking for a good story, but they both discover there's more to life than money and headlines. Don't miss this classic!Buy from Amazon »

3. "Meet the Parents" (2000)

If you're looking for a listing of things not to do when you first meet your future in-laws, this is the movie for you. Some scenes like the cat and grandma's urn are hilarious. In the end, communication skills and honesty make things right again for Greg (Ben Stiller) and Pam (Teri Polo).Buy from Amazon »

4. "Runaway Bride" (1999)

When Ike Graham (Richard Gere) writes a column about Maggie Carpenter (Julia Roberts), she is outraged and he gets fired. Predictable, but fun romantic plot about the importance of knowing and loving oneself before beginning the journey of marriage.More »

5. "Guess Who is Coming to Dinner" (1967)

Although made in the 1960's, this film about bi-racial marriage is still relevant today. Two scenes are especially poignant: Mrs. Prentice's (Beah Richards) comments about marriage and Matt Drayton's (Spencer Tracy) speech about his love for Christina Drayton (Katherine Hepburn).More »

6. "Only You" (1994)

This romantic comedy about Faith (Marisa Tomei) seeking her other half in Italy has the message that we shouldn't settle for less when it comes to marriage. A side story concerning staying true to marriage vows is about sister-in-law Kate (Bonnie Hunt) who is having a crisis when her own marriage lacks romance and caring.More »

7. "Moonstruck" (1987)

Unlucky in love, Loretta (Cher) wants her marriage to Johnny (Danny Aiello) to have the blessings of both her father and the church. Romantic sparks fly when she contacts Johnny's estranged brother Ronny (Nicholas Cage). At the same time her parents Rose (Olympia Dukakis) and Cosmo (Vincent Gardenia) are having marital problems. One of the messages is to not have low expectations in life.More »

8. "Crazy From the Heart" (1991)

It's OK to follow your heart. It's healthy to live in the moment. It's good to ignore other's opinions at times. Charlotte (Christine Lahti) discovers all this when she throws caution and bigoted, chauvinistic boyfriend Dewey (William Russ) out the window and marries Ernesto (Ruben Blades) after a very short courtship. Ernesto's persistence and kindness teach Charlotte the true meaning of love.Buy from Amazon »

9. "When Harry Met Sally" (2000)

Can friends who become lovers ever be friends again? We sure hope so. This film looks at the interrelated nature of love and friendship between Harry (Billy Crystal) and Sally (Meg Ryan). The clever glimpses of elderly couples sharing how they met are delightful. Love can sometimes be right around the corner.Buy from Amazon »

10. "Pillow Talk" (1959)

Brad Allen (Rock Hudson) and Jan Morrow (Doris Day) dislike one another when they share a telephone line. After seeing Jan, Brad decides he would like to know her better but doesn't stand a chance. Assuming the identity of Rex Stetson, Brad successfully woos Jan until she discovers his deceit. This great classic romantic comedy teaches the importance of being themselves during courtship.More »