5 Timeless Rom-Coms for Valentine’s Day

Posted on: Feb 13, 2024

Photo Credit: SeventyFour // Shutterstock

By Benjamin Hickson

Valentine’s Day is a celebration of love and romance where couples get to celebrate the love and joy they have for each other. For many couples, Valentine’s Day is an opportunity to visit fantastical stories of love and triumph through classic rom-coms. While some might argue that the nature of rom-coms is cliche, there is something comforting about the simplicity and familiarity of these warmhearted stories.

This Valentine’s Day let’s take a look at some of the most well-loved rom-coms of the past few decades.

When Harry Met Sally

Rob Reiner’s When Harry Met Sally (1989) was one of the earliest films to reshape the romantic comedy genre. Meg Ryan and Billy Crystal lead the film in an exploration of their evolving relationship over 12 years. What helps distinguish the film from its contemporaries is its clever script, authentic performances and a contemplation on the possibility of platonic friendship between men and women. This movie isn’t just any rom-com, but a benchmark in the genre that is celebrated for its realistic portrayal of relationships and its memorable moments.

Pretty Woman

Garry Marshall’s Pretty Woman (1990) stands as an influential entry in romantic comedy. Featuring Julia Roberts and Richard Gere, the film tells of a modern fairy tale about a wealthy businessman and a high-spirited prostitute as they unwittingly fall in love. Its persistent allure emerges from the fusion of romantic fantasy and social commentary, defying the conventional norms of its time. Julia Roberts’ breakout performance and the film’s fairy-tale elements collectively elevate the film beyond the typical rom-com and solidify it as a timeless classic.


This 2011 film directed by Paul Feig, has become a timeless classic due to its exceptional humor, relatable characters and innovative take on the romantic comedy genre. The story revolves around Annie Walker, played by Kristen Wiig, as she navigates the challenges of being maid of honor and contends with other bridesmaids for her best friend Lillian’s attention.

The film is an unusual entry into the genre because of how it perfectly blends elements of slapstick comedy with genuine moments. Wiig’s portrayal of Annie, alongside a talented ensemble cast including Melissa McCarthy, creates an authentic depiction of female friendships. Bridesmaids strikes a balance between outrageous comedy and heartfelt scenes, resonating with audiences and earning its status as a timeless classic in the romantic comedy genre.

The Big Sick

The 2017 film directed by Michael Showalter, offers a vital update to the romantic comedy genre. Based on Kumail Nanjiani and Emily V. Gordon’s real-life romance, the film explores cultural and personal identity in cross-cultural relationships. Nanjiani, playing a version of himself, navigates family expectations and love complexities.

What really sets it apart is its infusion of authenticity into the rom-com formula, tackling illness and genuine emotions. This film challenges traditional conventions, demonstrating that romantic comedies can be both entertaining and thought-provoking, making it a significant evolution in the genre.

Sleepless in Seattle

This 1993 film is one of Nora Ephron’s earliest films, and stars perhaps one of the best 90s rom-com duos, Meg Ryan and Tom Hanks. In the film, Meg and Tom play Annie and Sam, who after the death of his wife, moves to Seattle with his son. When his son calls in to a talk-radio program to find a new wife for his father, Sam reluctantly gets on the line to discuss his feelings, so when Annie, a Baltimore Sun reporter, hears Sam speak she falls for him. Unsure where it will lead, she writes Sam a letter asking him to meet her at the Empire State Building on Valentine’s Day.

The chemistry between Hanks and Ryan is palpable, and their on-screen dynamic enhances the movie’s emotional appeal. The direction and well-crafted script infuse the film with a timeless quality that resonates with audiences for generations. The movie effortlessly elicits laughter, tears and a sense of romantic optimism, solidifying its place as a cherished classic within the romantic comedy genre.

With their captivating narratives, genuine performances and reflections on society, these timeless rom-coms have become cultural touchstones. Whether challenging norms like Pretty Woman or redefining the genre with wit and authenticity like When Harry Met Sally, these classics serve as more than mere entertainment. These films help shape and influence our perceptions of love, relationships and the human experience.

Benjamin Hickson is an aspiring producer and production coordinator who has 4+ years experience working on various Film and TV projects. He has a background in Public Relations and served for six years in the military. He also has passion for travel and aims to increase LGBTQ+ representation in the entertainment industry.

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