13 Best Rom-Coms From the ’90s That Still Make Us Swoon

The ’90s were a golden era for romantic comedies, producing films that have continued to make audiences swoon for decades. These movies not only delivered heartwarming love stories but also introduced unforgettable characters and iconic moments. From the quirky to the classic, the rom-coms of the ’90s captured the magic of love in a way that still resonates today. Whether it’s the charm of a small-town romance or the drama of finding love in the big city, these films have a timeless quality. They offer the perfect blend of humor, romance, and emotional depth that keeps us coming back for more.

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When Harry Met Sally (1989)

This classic rom-com is considered one of the best for its witty dialogue and strong performances by Billy Crystal and Meg Ryan. It follows the journey of two friends, Harry and Sally, who question whether men and women can truly just be friends without romantic feelings getting in the way. The movie showcases their evolving relationship over the years, filled with iconic scenes and memorable quotes. The chemistry between the leads makes the story engaging and timeless.

The movie’s exploration of love, friendship, and the complexities of relationships resonates with viewers even today. It tackles the question of whether you can find true love in an unexpected friendship, with humor and heart. The iconic scene at Katz’s Deli is one of the most memorable moments in romantic comedy history, cementing this film as a cultural touchstone.

Sleepless in Seattle (1993)

In this heartwarming film, Tom Hanks and Meg Ryan reunite after their successful collaboration in “Joe Versus the Volcano.” The story revolves around Sam, a widower in Seattle who unintentionally becomes a symbol of romance when he shares his feelings on a radio show. This leads to an emotional connection with Annie, a woman in New York who feels compelled to meet him despite being engaged to another man.

The film’s charm lies in its blend of emotion and humor, with the cityscape of both Seattle and New York serving as beautiful backdrops. Its focus on destiny and love at first sight captivates audiences, making it one of the most beloved rom-coms from the era.

Notting Hill (1999)

Starring Hugh Grant and Julia Roberts, this film tells the story of William, a humble bookstore owner, and Anna, a famous movie star, who fall in love despite their vastly different worlds. The charming setting of Notting Hill in London adds to the film’s allure, with breathtaking scenery and an unforgettable soundtrack. The film’s sweet moments and realistic portrayal of a celebrity romance made it an instant favorite.

One of the film’s standout qualities is its heartwarming narrative, which proves that love can bridge any gap, no matter how challenging the circumstances. It’s a beautiful exploration of finding love in the most unexpected places, with a perfect mix of humor and sincerity.

10 Things I Hate About You (1999)

A modern adaptation of Shakespeare’s “The Taming of the Shrew,” this teen rom-com stars Heath Ledger and Julia Stiles in memorable roles. Set in a high school, the movie follows the story of Kat and Patrick, who navigate the complexities of love and personal growth. With sharp humor, relatable characters, and plenty of heart, it became an instant classic for audiences of all ages.

The film’s success is in large part due to its stellar cast and witty dialogue, along with a romantic plot that feels genuine and fresh. The chemistry between Ledger and Stiles is undeniable, making their characters’ journey from enemies to lovers both exciting and believable.

You’ve Got Mail (1998)

Tom Hanks and Meg Ryan teamed up once again for this charming tale about two people who fall in love over email without knowing they’re also business rivals in real life. The film brings together themes of love, technology, and the changing nature of relationships in the digital age. The chemistry between the leads, along with the film’s quirky humor, made it a standout during the late ’90s.

The film’s sweet premise, paired with its beautiful New York City backdrop, provides a lighthearted yet touching exploration of love in the modern world. The idea of anonymous connection that blossoms into something real resonates with viewers even today, making it a timeless favorite.

Runaway Bride (1999)

In this film, Julia Roberts stars as a woman who has a habit of leaving her fiancés at the altar, until she meets a reporter, played by Richard Gere. As she tries to figure out why she cannot commit to a relationship, she starts to question her true feelings for the reporter. The movie combines comedy with real emotional depth as it examines personal growth and self-discovery.

The film’s humor, paired with its deep exploration of commitment and fear of intimacy, makes it both entertaining and thought-provoking. The dynamic between Roberts and Gere, who previously starred together in “Pretty Woman,” adds a layer of nostalgia that makes this movie a fan favorite.

My Best Friend’s Wedding (1997)

Julia Roberts stars as Julianne, who realizes she is in love with her best friend Michael just as he is about to marry someone else. The movie combines humor, drama, and a great deal of tension as Julianne tries to stop the wedding, all while learning important life lessons about love and friendship. It’s a rom-com that adds layers of complexity to the typical love triangle plot.

The film is particularly memorable for its sharp dialogue and Roberts’ excellent performance. The exploration of unrequited love, friendship, and personal growth adds depth to the film, making it much more than just a typical romantic comedy.

The Wedding Planner (2001)

Starring Jennifer Lopez and Matthew McConaughey, this rom-com follows the story of a wedding planner who falls in love with the groom of one of her clients. The film is full of romantic tension, humor, and misunderstandings that make for an engaging watch. Lopez and McConaughey’s chemistry drives the story, as their characters’ connection deepens despite the obstacles they face.

This movie successfully balances humor with romance, offering a story that is both funny and heartfelt. The themes of destiny and love are explored in a charming way, making this film a perfect choice for anyone looking for a feel-good rom-com.

Pretty Woman (1990)

One of the most iconic rom-coms of the ’90s, “Pretty Woman” stars Richard Gere as a wealthy businessman and Julia Roberts as a woman he hires for companionship. The movie’s charm lies in its exploration of class differences, romantic tension, and the transformative power of love. Roberts’ performance as Vivian turned her into a beloved figure, and the film’s fairy-tale ending made it a hit with audiences around the world.

The chemistry between Gere and Roberts, along with the film’s unforgettable soundtrack, has solidified this film as one of the most enduring rom-coms of all time. Its mixture of humor, romance, and heart makes it a must-watch for fans of the genre.

Clueless (1995)

This modern-day take on Jane Austen’s “Emma” stars Alicia Silverstone as Cher Horowitz, a wealthy high school student who plays matchmaker for her friends and herself. The film’s witty script and memorable characters make it one of the most iconic teen rom-coms of the ’90s. Cher’s journey of self-discovery, coupled with her evolving relationship with the charming, but misunderstood, Josh, gives the movie depth beyond its high school setting.

“Clueless” also became famous for its fashion, with Cher’s wardrobe influencing trends of the decade. The film’s combination of humor, heart, and a little bit of awkwardness resonates with audiences, making it a standout film in the genre.

While You Were Sleeping (1995)

Starring Sandra Bullock, this romantic comedy follows Lucy, a lonely transit worker who saves a man from an oncoming train and is mistaken for his fiancée while he’s in a coma. The story takes a heartwarming turn as Lucy falls in love with the man’s brother, played by Bill Pullman. The film is filled with humor, romance, and the charm of a small-town setting.

The film’s appeal lies in its unique premise and strong performances, especially by Bullock, who brings warmth and humor to her character. The heartwarming story of love and family makes it a feel-good rom-com that still holds up decades later.

50 First Dates (2004)

Although it’s technically from the early 2000s, this rom-com features Drew Barrymore and Adam Sandler in a story about Henry, who falls in love with Lucy, a woman with short-term memory loss. Every day, she forgets him, so Henry has to win her heart anew every single day. The film is funny, emotional, and filled with sweet moments that tug at the heartstrings.

The film’s exploration of love, patience, and the importance of making an effort in relationships adds depth to the usual rom-com plot. Barrymore and Sandler’s dynamic adds a unique charm that elevates this movie beyond a typical romantic comedy.

Two Weeks Notice (2002)

In this charming rom-com, Sandra Bullock plays Lucy, a lawyer who agrees to work for a wealthy businessman, played by Hugh Grant. Over time, their relationship shifts from employer-employee to something much more, full of romantic tension and hilarious moments. The chemistry between the two leads, combined with their witty banter, makes for a fun and engaging romantic comedy.

The movie shines thanks to its lighthearted nature and the lovable, flawed characters at its core. Bullock and Grant’s performances bring warmth and humor to the story, making it one of the more endearing rom-coms of the early 2000s.

This article originally appeared on Avocadu.