15 Early 2000s Rom Coms That Still Hold Up

When you think about the early 2000’s rom coms, you will inevitably have a warm, nostalgic feeling. In case anyone fancies a refresher, here is a list of the best rom coms from the early 2000’s that really stand the test of time.

  1. Bridget Jones’ Diary Here, thirtysomething singleton Bridget makes her way in the world as she negotiates new relationships, old friends, and one contentious mini-break. It had the camp gay best friend at a time when few films did even that. Also, it had totally relatable mother-daughter anxieties as well as a good helping of Colin Firth in Christmas sweaters. British comedy at its best – even with an American leading lady!
  2. How to lose a guy in ten days This film is often slept-on. Kate Hudson plays the emotionally unavailable hustler that young bachelors pay off to pretend to be dating. This is mostly to get the parents off their backs and it is fake dating at its best. Guess what happens when she meets this guy…
  3. 50 first dates Here, nice guy Adam Sandler has to repeatedly woo his girlfriend, who suddenly has bouts of unexplained amnesia and forgets that they’re together. Here, Adam Sandler offers charm and wit as he tries to win back Drew Barrymore on repeat. It’s sweet, good fun, and really holds up on rewatching.
  4. The 40-year-old Virgin I know lots of people will say that this is more of a slapstick coming-of-age comedy than a rom-com, but it is a quality feel-good film. Here, we observe Steve Carrell in his quest to get laid. It reminds us that it’s okay to come to romantic relationships at your own pace.
  5. Forgetting Sarah Marshall This is another great combination of a likable funny guy meeting a woman who is immeasurably out of his league. The story follows Jason Segel when his ex, Mila Kunis leaves him on an island in the company of Kristen Bell, his new love interest. You lose yourself in the humor. It’s as wholesome as it is fun.
  6. The Proposal This is the gold standard of rom coms in the 2000’s. Sandra Bullock is every inch her fast-talking powerhouse strong career-woman-in-the-city character. Ryan Reynolds, in equal measure, is the affable, charming but emotionally unaware office lackey. These two fall in love on a trip to Alaska when they convince his family that they’re together for a green card marriage. Enemies to lovers in the extreme, and some laugh-out-loud cameos.
  7. Legally Blonde Reese Witherspoon. Legal drama. Sorority superiority and the unexpected twists of slimy professors and rehabilitated mean girls. Can I get a “Hell yeah!”? Legally Blonde set the tone of much of the “I can be pretty and clever” paradox in the early 2000s. It was a trailblazer for the “never lower your standards” mantra.
  8. 13 Going on 30 This is a heartfelt, coming-of-age My Girl meets Freaky Friday. A young girl suddenly finds herself waking up aged thirty years old. Imagine! It taught us not to want to grow up too fast.
  9. The Devil Wears Prada A young girl in the big city. She’s in a job that she is dismissive of at first but comes to find fulfillment in by the end. Meryl Streep, Anne Hathaway, and Emily Blunt are all firing on all cylinders in this one. The fashion. The tropes. The trashy boyfriend who never really does enough to deserve the leading lady. This film runs the gamut on how to stop holding yourself back.
  10. A lot like love You know when you just can’t get over someone even though you never actually went out? This is what Ashton Kutcher and Amanda Peet do here, in a series of wrong place and wrong times. Don’t worry, eventually, they do realize they’re the right people for each other.
  11. Get over it This is the lesser-known contemporary Shakespeare adaptation of A Midsummer Night’s Dream. It distills all the things a guy will do to get a girl, including signing for the school play and getting a friend to tutor him on love. Have a wild guess about who he ends up falling for.
  12. The Sweetest thing Here, we have a host of famous actresses including Cameron Diaz go on a quest to search for a man that Diaz found at a club once. This is one for your friends to sit down with a glass of wine to enjoy. It’s an absolute riot.
  13. Whatever it takes Rom com royalty Shane West stars here as the nerd who falls for a popular girl and James Franco who falls for West’s best friend. Both soon realize that they’re after the wrong person, but not before good fun and great jokes are had!
  14. Bride Wars Here, Kate Hudson and Anne Hathaway fight it out for the best wedding when these two best friends accidentally schedule their weddings on the same day. Watch as the madness ensues and relationships are put to the test.
  15. Catch and release Our Lord and Savior Jennifer Garner attends her fiance’s funeral. This is a sad one, but a great rom-com that really tugs at the heartstrings as she finds new friends and relationships. It reminds us that love is everywhere, and that there’s always hope when you need to let someone go.
Hannah has a Masters degree in Romantic and Victorian literature in Scotland and spends her spare time writing anything from essays to short fiction about the life and times of the frogs in her local pond! She loves musical theatre, football, anything with potatoes, and remains a firm believer that most of the problems in this world can be solved by dancing around the kitchen to ABBA. You can find her on Instagram at @_hannahvic.