10 Rom-Com Classics From the 2000s Everyone Still Loves

10 Rom-Com Classics From the 2000s Everyone Still Loves

The 2000s gave us some of the most memorable romantic comedies that still make us laugh and cry today.

These films captured the awkwardness of dating, the joy of falling in love, and the messy reality of relationships in ways that felt fresh and real.

Whether you’re looking for a cozy movie night pick or want to revisit old favorites, these rom-coms prove that great love stories never go out of style.

1. (500) Days of Summer (2009)

Tom Hansen believes Summer Finn is his soulmate, but she doesn’t believe in true love.

The story jumps around in time, showing us 500 days of their relationship in a non-linear way that mirrors how we actually remember our past relationships.

This film broke the rom-com mold by showing that not every love story has a fairy-tale ending.

It’s honest about how we sometimes create fantasies about people instead of seeing who they really are.

Joseph Gordon-Levitt and Zooey Deschanel deliver performances that feel incredibly real and relatable.

The movie teaches an important lesson about the difference between loving someone and being in love with the idea of them.

2. Forgetting Sarah Marshall (2008)

Peter Segel gets dumped by his famous actress girlfriend and decides a Hawaiian vacation will help him move on.

Unfortunately, he runs into his ex and her new rockstar boyfriend at the same resort.

What could have been a disaster turns into something beautiful as Peter meets Rachel, a hotel employee who helps him see his worth.

The humor is sharp and sometimes crude, but underneath it all is a genuinely touching story about healing after heartbreak.

Jason Segel wrote and stars in this film, bringing vulnerability and honesty to a character who’s completely lost.

The tropical setting provides the perfect backdrop for rediscovery, laughter, and eventually finding someone who truly appreciates you.

3. My Big Fat Greek Wedding (2002)

Toula Portokalos is a 30-year-old Greek woman working in her family’s restaurant, feeling stuck and invisible.

When she finally decides to make changes in her life, she catches the eye of Ian Miller, a non-Greek teacher who’s completely different from anyone her traditional family would approve of.

The culture clash creates hilarious situations as Ian tries to win over Toula’s massive, loud, and loving Greek family.

From Windex as a cure-all to lamb on the spit, the movie celebrates cultural traditions while showing that love can bridge any gap.

Nia Vardalos wrote and starred in this indie hit that became a surprise blockbuster, proving audiences craved authentic, relatable stories about real people finding confidence and love.

4. The Holiday (2006)

Two women from different continents decide to swap houses for the holidays, hoping to escape their complicated love lives.

Cameron Diaz plays a successful LA businesswoman while Kate Winslet is a heartbroken journalist from a charming English village.

What starts as a simple vacation becomes a journey of self-discovery and unexpected romance.

Both women find themselves falling for local men they never planned to meet.

The movie perfectly captures that warm, fuzzy feeling of finding love when you least expect it.

With snowy landscapes, cozy fireplaces, and genuine chemistry between all the characters, it’s become a holiday season staple that people watch year after year.

5. Hitch (2005)

Alex Hitchens makes his living as a professional dating consultant, helping awkward men win over the women of their dreams.

He’s mastered every trick and technique for creating romantic connections, believing he’s got love completely figured out.

Everything changes when he meets Sara Melas, a gossip columnist who challenges all his carefully crafted rules.

For the first time, Hitch finds himself stumbling, second-guessing, and realizing that real connection can’t be manufactured through tricks.

Will Smith brings charm and humor to a character learning that authenticity beats strategy every time.

The movie cleverly shows both sides of modern dating while delivering laughs and genuine romantic moments that still resonate today.

6. 50 First Dates (2004)

Henry Roth is a commitment-phobic veterinarian in Hawaii who finally meets someone special named Lucy.

There’s just one problem: she has short-term memory loss and forgets him completely every single day.

Instead of giving up, Henry creates elaborate ways to make Lucy fall for him over and over again.

The premise could have been purely comedic, but the film finds real emotional depth in exploring what it truly means to love someone unconditionally.

Adam Sandler and Drew Barrymore have wonderful chemistry that makes you root for this impossible relationship.

The movie asks beautiful questions about identity, memory, and whether love can transcend even the biggest obstacles we face.

7. Knocked Up (2007)

Alison Scott is an ambitious entertainment journalist whose life is perfectly on track until a one-night stand with slacker Ben Stone results in an unexpected pregnancy.

The two barely know each other and couldn’t be more different in their life goals and maturity levels.

What follows is a surprisingly honest look at two people trying to figure out if they can build a relationship while preparing for parenthood.

The humor is raw and sometimes uncomfortable, but it captures the reality of growing up fast when life forces your hand.

Seth Rogen and Katherine Heigl navigate the awkwardness brilliantly, showing that sometimes love grows from the most unlikely circumstances when people choose to show up and try.

8. Serendipity (2001)

Jonathan and Sara meet by chance while Christmas shopping in New York and feel an instant connection.

Instead of exchanging numbers like normal people, Sara suggests they leave their fate to the universe, separating and trusting destiny to bring them back together.

Years later, both are engaged to other people but can’t shake the memory of that magical night.

The film follows their separate journeys as signs and coincidences seem to pull them back toward each other.

John Cusack and Kate Beckinsale create a romance that feels both fantastical and believable, making you wonder about the role of fate in your own life.

It’s a love letter to New York City and the idea that some connections are simply meant to be.

9. Bridget Jones’s Diary (2001)

Bridget Jones is a 32-year-old single woman in London who decides to take control of her life by keeping a diary.

She’s relatable in every way: she worries about her weight, says the wrong things at parties, and can’t seem to choose between her charming boss and her childhood friend.

Renee Zellweger completely transforms into this beloved character, capturing all of Bridget’s insecurities and humor with perfect British charm.

The love triangle between Bridget, the caddish Daniel Cleaver, and the seemingly stuffy Mark Darcy keeps you guessing throughout.

Based on Helen Fielding’s novel, the movie celebrates imperfect women trying to navigate modern life and love without losing themselves in the process.

10. Definitely, Maybe (2008)

Will Hayes is going through a divorce when his curious daughter asks him to tell her the story of how he met her mother.

He agrees but changes the names, turning his romantic history into a mystery for her to solve.

Through flashbacks, we see Will’s relationships with three very different women over the course of a decade.

Each relationship taught him something important about love, timing, and what he really wanted from life.

Ryan Reynolds brings warmth and nostalgia to a character reflecting on past choices and roads not taken.

The film cleverly shows how our romantic journeys shape us, and how sometimes the right person has been there all along waiting for the right moment.