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Classic Rom-coms of the ‘90s and ‘00s

They may be formulaic and predictable, they may create unrealistic expectations about love, but they’re also a very particular brand of comforting, which no one can take away from them. So grab your significant other or a pint of your favorite ice cream and get the tissues ready, ‘cause these beloved romantic comedies of the 1990s and 2000s are not only delightfully nostalgic but are also bound to bring tears of joy to your face.

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  • Created February 14, 2022 by
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Pretty Woman

1990

A young Los Angeles prostitute, Vivian Ward, is picked up off the streets by high-powered businessman Edward Lewis. He decides to hire her as an escort for some social and business events, but as their agreed upon week rolls by, they quickly realize they are meant for each other.

Four Weddings and a Funeral

1994

At the wedding of Angus and Laura in Somerset, unmarried best man Charles and his friends – his flatmate Scarlett, Fiona and her brother Tom, partners Gareth and Matthew, and Charles’ brother David – endure the festivities. At the reception, Charles becomes smitten with Carrie, an American, and the two spend the night together. In the morning, Carrie jokingly demands that Charles propose to her, observing that they may have “missed a great opportunity,” and she leaves for America.

My Best Friend's Wedding

1997

Food critic Julianne does her sneaky best to sabotage her pal Michael's wedding to rich college student Kimmy after realizing she wants him for herself.

There's Something About Mary

1998

Ted, a geek, attempts to track down his high-school sweetheart Mary and hires a private detective to know her whereabouts. He soon realises that he has to compete with others in order to impress her.

You've Got Mail

1998

New Yorker Kathleen Kelly owns a small children's book store, that comes under competition from Joe Fox's giant literary conglomerate "Fox Books." As the two businesses meet head-to-head the pair become arch rivals, but fail to realize that the online romance they are conducting anonymously is with each other.

She's All That

1999

High school class president Zack Siler makes a bet with his friends that he can turn artistic, bespectacled nobody Laney Boggs into prom queen.

10 Things I Hate About You

1999

On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date...until her ill-tempered, completely un-datable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own!

Notting Hill

1999

A chance encounter brings together reserved bookstore owner William Thacker and Hollywood icon Anna Scott, who forge an improbable romance.

The Wedding Planner

2001

Mary Fiore is San Francisco's most successful supplier of romance and glamor. She knows all the tricks. She knows all the rules. But then she breaks the most important rule of all: she falls in love with the groom.

A Walk to Remember

2002

Two North Carolina teens, Landon Carter and Jamie Sullivan, are thrown together after Landon gets into trouble and is sentenced to perform community service.

About a Boy

2002

Will Freeman lives a serene and luxurious lifestyle devoid of responsibility in London thanks to substantial royalties left to him from a successful Christmas music composed by his father. Marcus Brewer is a young teenager with a single mother who doesn't fit in at school. Will joins a single-parents group after a successful fling with a single mother in an attempt to find others, making up an infant son "Ned" who conveniently spends most of his time with his absentee mother. Will gains Marcus's interest and trust after he lies to a park ranger to cover up for Marcus accidentally killing a duck by throwing his mother's cottage loaf at it. Afterward, when Will takes Marcus home, they find Fiona (Marcus's mother) in the living room, overdosed on pills in a suicide attempt.

Sweet Home Alabama

2002

Feeling doubtful about her recent engagement to the city's most eligible bachelor, a New York fashion designer returns to her hometown and to her husband, who refuses to divorce her, but does she still hold a torch for her husband?

Maid in Manhattan

2002

Marisa Ventura, a single mother raising her 10-year-old son Ty, works as a maid at the Beresford Hotel in the heart of Manhattan. When not in school, Ty spends time with Marisa's fellow hotel workers, who think she can be promoted to management.

How to Lose a Guy in 10 Days

2003

An advice columnist, Andie Anderson, tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. Her editor, Lana, loves it, and Andie goes off to find a man she can use for the experiment. Enter executive Ben Berry, who is so confident in his romantic prowess that he thinks he can make any woman fall in love with him in 10 days. When Andie and Ben meet, their plans backfire.

Love Actually

2003

Eight London couples try to deal with their relationships in different ways. Their tryst with love makes them discover how complicated relationships can be.

Along Came Polly

2004

Reuben Feffer, a risk analyst for life insurance, is celebrating his honeymoon with newlywed wife, Lisa Kramer, on the island of Saint Barthélemy, but catches her having sex with Claude, a French people scuba instructor. Returning home to New York alone, he attempts to piece his life back together. Reuben goes to an art gallery with his friend, Sandy Lyle, where he runs into former Middle school classmate Polly Prince.

50 First Dates

2004

Henry Roth (Adam Sandler) is a veterinarian at Sea Life Park on the island of Oahu, Hawaii. He has a reputation of Promiscuity female tourists and does not display any interest in committing to a serious relationship. One day, at Hukilau Café, he meets a young woman named Lucy Whitmore. Believing her to be a local, he avoids introducing himself, but the next day he comes back. He and Lucy hit it off instantly and she asks him to meet her again tomorrow morning.

The Notebook

2004

Two young lovers are torn apart by war and class differences in the 1940s in this adaptation of Nicholas Sparks's best-selling novel.

Monster-in-Law

2005

Charlie Cantilini (Jennifer Lopez) is a Temporary work/Dog walking#Professional dog walkers/Yoga and aspiring fashion designer from Venice, Los Angeles, California, who meets doctor Kevin Fields (Michael Vartan). She thinks he is gay at first, based on a lie Kevin's former girlfriend Fiona (Monet Mazur) told her. But then Kevin asks her out, and Charlie believes that she has finally found the right man.

Failure to Launch

2006

A thirty-something is still living with his parents until they hire an interventionist to help him graduate out of the house. That's when the fun begins.

She's the Man

2006

Viola Hastings is a teen girl who plays for Cornwall’s soccer team until the team gets cut. Meanwhile, her twin brother, Sebastian, is supposed to enroll in Illyria, an elite boarding school, but he secretly goes to London with his fledgling band instead. Viola agrees to cover for him and decides to pass herself off as Sebastian, in hopes of joining their boys' team and beating Cornwall to prove their coach and her cocky ex-boyfriend, Justin, wrong. With the help of her stylist friend, Paul, she is transformed into "Sebastian" and attends Illyria in his place.

27 Dresses

2008

After serving as a bridesmaid 27 times, Jane is shocked when her younger sister announces her engagement to the man she loves. Meanwhile, she also meets a cynical journalist who has a hidden agenda.

What Happens in Vegas

2008

In New York City, high-strung equity trader Joy Ellis McNally is dumped by her fiancé at a surprise birthday party she throws for him. At the same time, easy-going carpenter Jack Fuller is fired from his job by his father, Jack, Sr. Both become emotionally distraught and, with best friends Toni "Tipper", a bartender, and Jeff "Hater", a lawyer, take a debauched trip to Las Vegas.

Nick and Norah's Infinite Playlist

2008

Nick O'Leary is a straight bass player in a queercore band that is searching for a name but tentatively calls themselves The Jerk-Offs. A teenager from Hoboken, New Jersey, he is still heartbroken after his girlfriend, Tris, broke up with him three weeks, two days, and 23 hours ago and continues to make “breakup” mixtapes for her. Thom and Dev, his gay bandmates who both hate Tris, convince Nick to perform at a club because his favorite band—the legendary, publicity-shy Independent music band Where’s Fluffy? —is performing somewhere in New York City that night.

He's Just Not That Into You

2009

Love-hungry Baltimoreans deal with the pitfalls of human interaction in this big-screen adaptation of Greg Behrendt's best-selling book.

The Proposal

2009

When high-powered book editor Margaret faces deportation to her native Canada, the quick-thinking exec declares that she's actually engaged to her unsuspecting put-upon assistant Andrew, who she's tormented for years. He agrees to participate in the charade, but with a few conditions of his own. The unlikely couple heads to Alaska to meet his quirky family and the always-in-control city girl finds herself in one comedic fish-out-of-water situation after another. With an impromptu wedding in the works and an immigration official on their tails, Margaret and Andrew reluctantly vow to stick to the plan despite the precarious consequences.

(500) Days of Summer

2009

An offbeat romantic comedy about a woman who doesn't believe true love exists, and the young man who falls for her.