Movies About Dating: A Guide to the Best and Worst on Screen Romances

When it comes to dating, we all know that it can be a bit of a rollercoaster ride. From the highs of finding someone you really connect with to the lows of being ghosted or dealing with rejection, the dating world can be tough. But, as with most things in life, we can always turn to the movies for a little escapism and entertainment. In this guide, we'll take a look at some of the best and worst movies about dating, from the classics to the modern rom-coms.


When it comes to classic movies about dating, there are a few standouts that have stood the test of time. One of the most iconic is "The Graduate," which follows the story of Benjamin Braddock (Dustin Hoffman) as he starts an affair with Mrs. Robinson (Anne Bancroft), the wife of his father's business partner. While the movie may be over 50 years old, its themes of forbidden love and generational conflict still feel relevant today.

Another classic dating movie is "Annie Hall," which won four Oscars, including Best Picture. Directed by and starring Woody Allen, the movie follows the ups and downs of a relationship between Alvy Singer (Allen) and Annie Hall (Diane Keaton). With its witty script and realistic portrayal of relationships, "Annie Hall" is a must-watch for anyone who's ever been in love.

Modern Rom-Coms

In recent years, romantic comedies have become one of the most popular genres in Hollywood. While not all of them are winners, there are a few that stand out as modern classics. One of the most beloved is "Crazy Rich Asians," which follows the story of Rachel Chu (Constance Wu) as she travels to Singapore to meet her boyfriend's family. With its stunning visuals and heartwarming story, "Crazy Rich Asians" has become a fan favorite.

Another modern rom-com that deserves a spot on this list is "To All the Boys I've Loved Before." Based on the novel by Jenny Han, the movie follows high school student Lara Jean Covey (Lana Condor) as she navigates her feelings for her crushes after her secret love letters are accidentally sent out. With its charming leads and sweet story, "To All the Boys I've Loved Before" is perfect for a cozy night in.

Romantic Dramas

While rom-coms may get all the attention, there are plenty of romantic dramas that are just as worthy of our time. One of the best is "The Notebook," which tells the story of Noah (Ryan Gosling) and Allie (Rachel McAdams) as they fall in love in the 1940s. With its sweeping romance and tear-jerker ending, "The Notebook" has become a classic in its own right.

Another romantic drama worth watching is "Before Sunrise," which follows Jesse (Ethan Hawke) and Celine (Julie Delpy) as they spend one night together in Vienna. With its naturalistic dialogue and realistic portrayal of love at first sight, "Before Sunrise" is a must-watch for anyone who's ever been swept off their feet.

The Worst

Of course, not every movie about dating is a winner. There are plenty of stinkers out there that should be avoided at all costs. One of the most reviled is "Gigli," which starred Ben Affleck and Jennifer Lopez as two mobsters who fall in love. With its cringe-worthy dialogue and bizarre plot twists, "Gigli" is a prime example of what not to do when making a dating movie.

Another movie that falls flat in the romance department is "How to Lose a Guy in 10 Days." While it may have been a box office success, the movie's premise - a journalist tries to get dumped by her boyfriend as part of an article while he tries to make her fall in love with him - feels dated and sexist today. Plus, the chemistry between leads Kate Hudson and Matthew McConaughey leaves a lot to be desired.

Final Thoughts

While movies about dating may not provide all the answers when it comes to finding love in real life, they can certainly be entertaining and inspiring. From the classic romances to the modern hits, there's no shortage of dating movies to choose from. Just be sure to avoid the duds if you want to keep your faith in love intact!