One of the best things about Romantic Comedies is that, although they are predictable, they have the ability to pull at your heartstrings in so many different ways. Whether you are a hopeless, hopeful or cynical romantic, you can find enjoyment in any of the 2000s rom coms listed below. After many hours of research, I’ve compiled a list of the best romantic comedies from the 2000s, depending on what ‘feels’ you’re going for. If you are in the mood to have a good cry, to lose your breath laughing or simply enjoy some melodrama then get your pyjamas, blankets and friends ready!
1. The Proposal
If you are a fan of the enemies-to-lover plotline and enjoy the classic Ryan Reynolds, Sandra Bullock and Betty White comedy style, then this is the perfect movie for you. If you see yourself as a cynical romantic, you will most certainly relate to the hard-working editor Margaret, who coerces her assistant Andrew into becoming her fiancé in order to keep her job. Not only must Margaret and Andrew convince the immigration officials that they are in love, but also Andrew’s entire family when they attend Gammy’s 90th birthday weekend in his hometown Sitka, Alaska. This is definitely a must see if you’re looking for pure entertainment with a light-hearted romantic storyline that will make you excited for family weekends with your future in-laws. Anyone want to join me on a trip to Alaska?
2. A Walk to Remember
A Walk to Remember will break, flutter and mend your heart in an hour and forty-five minutes. If you are a hopeless or hopeful romantic, this is the perfect movie for you. As Landon falls in love with Jamie, an unapologetically genuine girl who is misunderstood by all those around her, they both learn the power of pure and unconditional love. If you are a book lover, I definitely recommend reading the book, since it’s even better than the movie (if that’s even possible!). This is the perfect film if you’re in the mood to see a good girl turn the bad boy good, to have a cathartic, ugly cry or if you’re looking to add some adorable date ideas to your bucket list.
3. Monster in Law
Jennifer Lopez is arguably one of the most well-known romantic comedy actresses of the 2000s, alongside legends like Katherine Heigl and Jennifer Aniston. After Viola’s only son Kevin gets engaged to a woman that she deems unsuitable, she takes it upon herself to do everything she can to break up Kevin’s engagement to Charlotte (played by Jennifer Lopez). As the title signifies, Viola is the kind of mother-in-law that I am sure any partner would subconsciously fear. I would definitely recommend this movie if you enjoy a romantic comedy that doesn’t tell the story of an easy romantic journey. Bonus points if you find watching a heated competition between two seemingly similar women funny. This movie can be boiled down to one question: how much would you go through for the person that you love?
4. How To Lose A Guy In 10 Days
If you’re in need of some tips on how to get your partner to break up with you, then make sure you have your notebook on hand. Based on the novel, this movie follows Ben and Andie as they both use each other to win separate bets. For her column, Andie must figure out how to lose a guy in ten days, and Ben must make Andie fall in love with him. This is the first movie on this list that fits the romantic comedy archetype to a tee. Kate Hudson and Matthew McConaughey have witty banter and an amazing connection, and I would say that it is arguably one of the most relatable rom coms to ever exist.
5. Just Friends
This movie takes the friends-to-lovers’ trope to a whole other level. Starring Ryan Reynolds and Amy Smart, it shows Chris going back to his hometown after ten years to fight for the love of his old best friend, Jamie. This movie tests the bounds of the ultimate platonic relationship, showing everyone who finds themselves trapped in the friend zone that there’s light at the end of the tunnel. Not only is this movie hilarious, it’s considered a Christmas movie as well! I would recommend this movie to anyone who enjoys the friends-to-dating storyline and likes watching realistic romantic comedies.
6. The Ugly Truth
Although it might not always be true in real life, this movie is a prime example of the advice many teachers have given me, and I am sure many other people, regarding romance. That advice being, if a boy is teasing and annoying you, he’s actually trying to show you how much he likes you. A prime example of the enemies-to-lovers’ plot, The Ugly Truth follows the uptight TV producer Abby, who is forced to compromise her integrity and work alongside the cocky TV-host Mike to produce his chauvinistic relationship advice. If you are in the mood for an unconventional romantic storyline and love watching two polar opposite people fall in love, then this is the movie for you.
7. Hitch
Starring Will Smith and Eva Mendes, I can confidently say that this is one of the most hilarious romantic comedies on this list. Matchmaker Alex Hitchens (Hitch) is famous in New York City for helping any man make the women of his dreams fall in love with him. As he helps the shy accountant Albert land the girl of his dreams, Hitch finds himself putting his own skills to the test after meeting a columnist named Sara. This is the perfect movie for when you feel like having a good laugh, but also enjoy watching a man put in a ton of effort to get the girl. One of my favourite things about Hitch is that it’s the perfect movie for any type of romantic because the connection between Hitch and Sara is so natural.
8. 13 Going on 30
This is one of my absolute favourite movies of all time! Thirteen-year old Jenna Rink wishes that she could be thirty, flirty and thriving. The day after her thirteenth birthday she wakes up to find her wish is granted, only to soon realize that problems don’t simply fade away with age. This movie reminds us that every moment of our life, both the good and bad, helps shape us into the person that we become. Jenna soon realizes that, although being an adult is fun, she should enjoy her youth while she can. I recommend this movie for anyone who’s in need of a pick-me-up and who likes the idea of falling in love with your best friend.
9. Mamma Mia
This timeless musical explores both romantic and platonic love, all bringing together Sofie’s epic love story. Days before her marriage to Sky, Sofie tells her best friends that she sent wedding invitations to her three potential fathers, inadvertently turning her mother’s life upside down. Although I do watch this movie alone from time to time, I find that I enjoy it much more when I watch it with my girlfriends. Mamma Mia is the perfect late-night flick if you are in the mood for singing, dancing and good music, all while visualizing yourself marrying your true love on a remote island in Greece.
10. Scott Pilgrim vs the World
This film may seem quite out of place considering all of the other recommendations I’ve written thus far, however Scott Pilgrim vs the World can definitely be considered a romantic comedy. Scott Pilgrim falls for the amazing Ramona, but must defeat all of Ramona’s exes before he can officially date her. I would definitely recommend this to anyone who is not a fan of the typical mushy rom-com. This movie focuses on comedy as the main genre, with the romance simply underscoring the plot’s development. This is the perfect movie if you’re in the mood to sit with friends and troll your exes, because believe me when I say almost every archetype of an ex is represented in this film. Also, can anyone out there truly resist a Michael Cera movie?
12. Sweet Home Alabama
After leaving her hometown for New York City to pursue her love of fashion, Melanie finds herself engaged to Andrew, the most eligible bachelor in the city (played by Patrick Dempsey). Despite trying to run from her past, Melanie is unable to escape as her old and new life start to blend together. If you are a fan of the childhood friend-to-lover romance, the city to country storyline, and enjoy a good love triangle, this is the perfect movie for you. I would recommend this movie when you feel like watching two soulmates rekindle their love, or if you’re in need of a reminder that we should always be following our hearts. I will admit there were moments where I was torn between who I wanted Melanie to end up with!
13. Deliver Us from Eva
I had to put this movie on the list because of the way that it shakes up the standard structure of a rom-com. Even though it’s not as well-known as the other films, it’s still a great movie. A loose adaptation of Shakespeare’s The Taming of the Shrew, it tells the modern love story of Ray Adams and Eva Dandridge. Ray is paid by his friends to seduce their girlfriend’s sister Eva, so that she’ll stop meddling in their relationships. Eva has always been known as the difficult woman, but will Ray finally be able to make her fall for a man? Vague description, I know, but if you are a fan of Shakespeare and his arguably messy love stories, this is the perfect movie for you. Did I mention that Gabrielle Union and LL Cool J star in the film?
14. The Break Up
After Brooke and Gary break up, they’re stuck living together since they both refuse to move out of their condo. As you could imagine, living with your ex isn’t the ideal situation, illustrated as Brooke and Gary’s arguments only escalate. This is another atypical rom-com because it skips over the entire relationship and begins at the breakup, focusing on the realities of a relationship post-split. I would suggest this movie to anyone who likes seeing exes bicker and try to make each other jealous, but also yearn for validation when feeling underappreciated in a relationship.
15. Because I Said So
Starring Diane Keaton as Daphne Wilder and Mandy Moore as Milly Wilder, this 2007 rom-com follows Daphne’s obsessive need to find a suitable boyfriend for her daughter. She even goes so far to post a dating ad online, so she can interview men before secretly setting them up with Milly. In search for her daughter’s perfect man, Daphne finds an unexpected love. Can you imagine your mom going behind your back to set you up with someone that she approved of beforehand… because I can! This movie reminds me of what I’m missing out on because I don’t have sisters, but my best friends are a great substitute. I would recommend this movie to anyone who’s looking for a good laugh and a good option to watch with your friends and/or your mother, if you’re brave enough.
16. 10 Things I Hate About You
An adaptation of Shakespeare’s The Taming of the Shrew, Julia Stiles and Heath Ledger star in this 1999 film as Kat Stratford and Patrick Verona. They play two similarly misunderstood outcasts who find themselves thrusted into an unexpected love story. Cameron, who’s in love with Kat’s younger sister Bianca, gets the school pretty boy to bribe Patrick so he’ll date Kat. Because Bianca can’t date until her older sister does, he thinks this is the only way Bianca will be available. One of my all-time favourites, this is the perfect movie for anyone who needs reminding that true love does exist, or for anyone with a thing for bad boys.
16. Kissing Jessica Stein
Kissing Jessica Stein follows the story of Jessica as she looks to find herself a life partner. Her fear of being alone forever begins to creep up on her, which leads her to reply to an ad called “Women Seeking Women”. I can imagine that this film was somewhat controversial in the early 2000s, especially for the romantic comedy genre. The story focuses on Jessica and Helen as they start questioning their sexualities, and ultimately come to the conclusion that they’re bisexual and/or sexually fluid. This is not by any means a ground-breaking LGBTQ+ film, but its encouragement of self-explration and representation of love outside Hollywood’s typical heteronormative structure is commendable. This is a great rom-com for when you feel like watching a movie that explores love stories outside of the normalized straight-couple romantic storyline!
17. Rumour Has It
After her sister announces her engagement, Sarah’s life is turned upside down when she finds out
that her father may not be her biological father. If that wasn’t bad enough, she also discovers that both her mother and her grandmother may be the muses of the infamous novel The Graduate. If you want to feel like your love life is not as messy as you think, then you have to watch this movie because it is the definition of complicated. Sarah, just like her grandmother, can be considered a cynical romantic, as she’s unsure if marriage is really for her. This is one of the only recommendations in this list where the main character is somewhat cynical, which is appealing if you don’t see yourself as a hopeless romantic.
18. John Tucker Must Die
John Tucker Must Die is a romantic comedy unlike no others. The movie deviates from the conventional storyline of the main character finding love, and instead focuses on getting revenge against the popular jock. I needed to include this movie on the list because, even though it’s not that great, the candid representation of playboys, heartbreak and revenge is very entertaining. Kate, who’s the new girl in school, is approached by three popular girls regarding the infamous John Tucker. Hurt by John who played all three of them, they ask Kate to help them seek revenge by making him fall in love with her. I would recommend this movie to anyone who has recently gotten their heart broken, as you get to watch the heartbreaker get what he deserves.
19. The Wedding Planner
Mary, a successful wedding planner who strives to make all of her customer’s dreams come true, has yet to find the right guy for her. In a near fatal accident, Mary is rescued by Steve, a handsome doctor. Just as she starts to believe she’s met the man of her dreams, she discovers that he is the fiancé of her newest client. This movie stars two amazing actors that you’ve already seen on this list, Jennifer Lopez and Matthew McConaughey. If you are not a hopeless romantic then this might not be the movie for you. But if you are, then get ready for a great movie with two love triangles and an all-around messy love story.
20. Just Go With It
Although this movie was not released in the early 2000s, I wanted to include it simply because it’s one of my all-time favourite romantic comedies. While this movie is not a tear-jerker, its light-hearted and entertaining nature still has the ability to pull at your heartstrings in different ways. This film follows Dr. Daniel Maccabee and his assistant Katherine as they pretend to be a divorced couple in order to cover up the lies Daniel told his new girlfriend Palmer. If you want to laugh until your stomach hurts, feel your heart swell and watch a family form then this is the perfect movie for you!
Hope you enjoy these movie suggestions!