Reddit Users Share Their Favorite Romantic Comedies from the '90s and 2000s

For those who also believe this genre has deteriorated over recent years.

If you feel like movies from the '90s and 2000s were cozier and more comforting – you're absolutely right. Here's our selection of romantic comedies from those years for a perfect evening.

French Kiss (1995)

Meg Ryan plays an American who travels to Paris to save her relationship, but meets a charming French con man played by Kevin Kline. A sparkling comedy about how love finds us in the most unexpected places.

Meg Ryan and Kevin Kline sitting on a bench, talking and laughing — French Kiss movie poster

Paris, wine, passion, and incredible chemistry between the leads – the perfect recipe for a romantic evening. According to Reddit user Pure Salamander2681, it's an unfairly underrated film.

Forgetting Sarah Marshall (2008)

Jason Segel's character goes through a painful breakup with a famous actress and heads to Hawaii to forget her. But fate has a cruel sense of humor – his ex shows up at the same hotel with her new boyfriend.

A man plays piano and sings while a woman nearby looks at him with bewilderment — Scene from Forgetting Sarah Marshall

A heartfelt and hilarious comedy about surviving heartbreak and finding the strength for new love. The film perfectly balances great humor with genuine emotion.

Crazy, Stupid, Love (2011)

Steve Carell goes through a divorce and gets seduction lessons from Ryan Gosling. A comedy about rediscovering yourself after a broken heart. Funny, touching, and surprisingly wise – this film shows that true love is worth any effort.

Ryan Gosling and Steve Carell sit at a bar counter, one gazing thoughtfully into his glass, the other watching — Ryan Gosling and Steve Carell in Crazy, Stupid, Love

She's Out of My League (2010)

Jay Baruchel plays an average airport security guard who meets an incredibly beautiful and successful woman (Alice Eve). Everyone around them is convinced she's too good for him, but sometimes opposites attract in the most unexpected ways.

Jay Baruchel and Alice Eve standing next to each other on the street, a scene from the film — Scene from She's Out of My League

A sweet comedy about self-doubt, genuine feelings, and how love doesn't recognize social boundaries.

My Best Friend's Girl (2008)

Dane Cook plays a professional "bad guy" hired to ruin first dates and send women running back to their exes. But when his best friend asks him to "handle" his ex-girlfriend, everything goes sideways. Kate Hudson in the lead female role brings special charm to the film.

Two men and a woman talking on the street between buildings in the city — Scene from "My Best Friend's Girl"

A comedy about friendship, betrayal, and how all's fair in love and war – until your own heart gets involved.

When Harry Met Sally (1989)

The eternal classic with Billy Crystal and Meg Ryan that forever changed how we think about male-female friendships. Sharp dialogue, unforgettable scenes, and philosophical musings on love. A film you'll want to watch again and again.

Meg Ryan and Billy Crystal each lying in their own bed talking on the phone — Scene from "When Harry Met Sally"

You've Got Mail (1998)

Young Tom Hanks and Meg Ryan fall in love through email correspondence – and this was way before Tinder – without realizing they're sworn enemies in real life.

Tom Hanks and Meg Ryan standing at the checkout counter in a store, talking to the cashier — Tom Hanks and Meg Ryan in "You've Got Mail"

A touching story about how technology can bring hearts together. The film overflows with warmth, humor, and faith that fate will always find a way to connect those who belong together.

Addicted to Love (1997)

Meg Ryan and Matthew Broderick play two jilted lovers who team up to destroy their exes' new relationships. What starts as a revenge plot gradually turns into attachment to each other.

Meg Ryan and Matthew Broderick in dark sunglasses peeking out from behind a door — Scene from "Addicted to Love"

A witty comedy about how revenge can turn into new love, and shared pain can become the beginning of healing. Great chemistry between the leads and plenty of laugh-out-loud moments.

Kate & Leopold (2001)

Career woman Meg Ryan meets a man from the 19th century who somehow ended up in modern-day New York. The contrast between his old-fashioned courtesy and the cynicism of the modern world creates countless comedic and touching moments.

Hugh Jackman and Meg Ryan sitting on a bench at night with the city in the background — Hugh Jackman and Meg Ryan in "Kate & Leopold"

Leopold (Hugh Jackman) marvels at simple things like elevators and toasters, but teaches Kate to value the romance she'd forgotten in her career chase. A fairy tale about how true love knows no boundaries of time.

50 First Dates (2004)

Adam Sandler falls for a woman (Drew Barrymore) who forgets the previous day every morning, so he has to win her heart over and over again. An incredibly touching story about devotion and patience. This film will make you laugh and cry at the same time.

Drew Barrymore and Adam Sandler talking on a sunny beach with greenery and water in the background — Scene from "50 First Dates"

Not a fan of romantic comedies? We've got you covered! We've previously written about the best 90s comedies and the best films with unpredictable endings.