12 Best Rom-Coms From the 2000s That Are Still Total Comfort Watches

2000s rom-coms are my thing. It’s probably because I’m extremely old-school when it comes to romance. I’m talking about a time when algorithms didn’t decide our “type,” and love unfolded through missed flights, fake relationships, chaotic meet-cutes, and monologues delivered with bated breath.

What I love most about 2000s rom-coms is how they inherit the flowery optimism of ‘90s romance and passionately blend it with social anxieties and chaos.

In terms of characters, women no longer waited for their knight in shining armor because they had begun wearing armor themselves, and men realized that emotional availability is hotter than toxic masculinity.

You could say the ‘90s rom-coms were the pioneers of sensible romance, even when logic sat in the backseat, allowing chemistry to do all the work.

Now that the vibe is set, let’s dive right into the most loved rom-coms from the 2000s.

12 Must-Watch Rom-Coms from the 2000s

1. Bridget Jones’s Diary (2001)

I hate the fact that Renée Zellweger’s Bridget Jones feels sorry for herself in the beginning, but save that, Sharon Maguire’s Bridget Jones’s Diary is a quintessential love triangle story, and quite an entertainer.

The narrative follows Bridget, a woman in her 30s who is frustrated with her seemingly failing life. Determined to change things, Bridget embarks on a journey of self-transformation, with a diary to hold herself accountable.

On her journey, she stumbles upon two potential Mr. Rights. Who will she choose?

2. How to Lose a Guy in 10 Days (2003)

Donald Petrie’s How to Lose a Guy in 10 Days somehow takes me back to Jeffrey Archer’s short story, Old Love. Two ambitious individuals, competing with each other professionally to prove two opposite ideas, only to end up in love.

The chemistry between Kate Hudson and Matthew McConaughey is electrifying, and the constant rivalry and tongue-in-cheek humor only add to the spice.

3. 13 Going on 30 (2004)

Adulthood appears to be a cakewalk only until you reach it. In this case, Jenna is pushed into it after she wishes to become an adult on her 13th birthday. Now that she’s 30, it’s time for her to discover the real joys of adulthood.

13 Going on 30 is a reality check for every teenager who thinks they are ready for adulting. At least, a movie will hurt less than a life lesson, and trust me, this one’s really fun!

4. The 40-Year-Old Virgin (2005)

Sex is such a taboo—both for the regressive and the progressive. The former bullies you if you have too much of it, and the latter bullies you if you don’t have enough. God, there’s no in between!

For Andy, life is hard—he’s 40 and a virgin. Not that he’s asexual, but with his personality and interests, it’s something that he’s pushed off for so long that it’s become his reality. It’s the people around him who seem to be more affected by his virginity. Some mock him and call him a loser; others are hell-bent on getting him laid. Amidst this, Andy finally falls in love with a woman.

Judd Apatow’s The 40-Year-Old Virgin explores masculine insecurities with just the right touch of humor. Also, Steve Carell steals the show in this one!

5. Amélie (2001)

Not only is Jean-Pierre Jeunet’s Amélie a masterclass in the use of colors, but it’s a rom-com that fills you with joy every time you rewatch it. It reminds you to have faith in your fantasies.

The narrative follows a young woman, Amélie, who embarks on a quest to find love and purpose in her life. As she battles her introversion, Amélie stumbles upon her one true love. Will she be able to claim her happiness?

Amélie will win your heart with its honest, charming exploration of love, while treating your eyes to some of the most picturesque visuals in film.

6. Bride and Prejudice (2004)

An interesting subversive adaptation of the classic Pride and Prejudice by filmmaker Gurinder Chadha, Bride and Prejudice is the perfect fusion of Bollywood bling and music with Hollywood flair.

The narrative follows the quirky love story of Lalita (Aishwarya Rai Bachchan) and Will (Martin Henderson), whose romance begins with a meet-cute at an Indian arranged marriage ceremony.

The narrative focuses on cultural contrasts to induce comedy while knitting a flamboyant love story with a happy ending.

7. Definitely, Maybe (2008)

Ryan Reynolds reigned the rom-com genre before he became our beloved Deadpool, and Definitely, Maybe is among the top two of his most notable works in this genre. The other one is The Proposal—we’ll come to that one right after this.

Adam Brooks’ Definitely, Maybe follows a single father as he recounts to his inquisitive 10-year-old daughter the story of how he fell in love with three women, leaving her to guess which one is her mother. The story is told against the backdrop of their ongoing divorce.

It uses similar notes to those of How I Met Your Mother, but it’s better.

8. The Proposal (2009)

The other notable 2000s rom-com starring Ryan Reynolds is Anne Fletcher’s The Proposal. Opposite Reynolds is Sandra Bullock.

The narrative follows Bullock’s Margaret, the editor of a publishing firm, who hatches an elaborate scheme with her assistant to avoid deportation. In exchange for a significant promotion, Andrew (Reynolds) must marry her, making her eligible for a green card. To evade the suspicions of the U.S. immigration agent, the two leave for Andy’s hometown to get married. However, all the faking leads to true love.

In another universe, HR is writing up a report against Margaret, but hey! This isn’t that universe, and Reynolds and Bullock are too good together!

9. Serendipity (2001)

Serendipity and Richard Linklater’s Before Sunrise may seemingly share the same premise; however, the two are nothing alike. While the latter is an intense, dramatic, and philosophical exploration of love, Peter Chelsom’s Serendipity portrays love as the greatest adventure and gamble in life.

Jonathan and Sara stumble upon each other in New York while buying Christmas presents for their respective partners, but the spark between the two is undeniable. The two spend some time together but eventually decide to part ways because of their existing romantic commitments, leaving their romance to fate.

Years later, they are engaged and soon to be married. But they haven’t been able to forget each other. So right before saying “I do,” the two decide to test the fate of their love, as they set out to find each other.

10. The Princess Diaries (2001)

If you can ignore the very misogynistic makeover trope (which thankfully doesn’t take center stage in the story), Garry Marshall’s The Princess Diaries is both an interesting and humorous story of self-discovery, topped with the right amount of romance.

Starring Anne Hathaway, the narrative follows a geeky, ordinary 15-year-old, Mia Thermopolis, who is suddenly informed that she is the heir to the throne of the European country of Genovia and is expected to take over. Now, she must decide, once and for all, if she wants to choose extraordinary over ordinary. But before that, she must also learn how to become a princess!

11. Love Actually (2003)

Richard Curtis’ Love Actually explores love in 10 different colors through 10 couples as they navigate their relationships a month before the holidays.

You’re bound to relate to one of them, and that’s what makes it an extremely fun watch. The ensemble cast also includes Alan Rickman, Emma Thompson, Bill Nighy, and more! Hello! What’s not to like?

12. 500 Days of Summer (2009)

We’ve all been Tom Hansen more than once in our lives!

Obsessing over the past to reflect upon what went wrong between a past love and what could have been done differently to not lose the person, after a bad breakup—the premise of Marc Webb’s 500 Days of Summer is so relatable that you immediately form a connection with the protagonists.

From there, it’s a bittersweet journey of love, loss, and grief, with moments of refreshing humor.

Did your favorite movie make it to this list? Let us know your top five in the list above!