If you live for the age of movies starring Amanda Bynes and Channing Tatum, read on. Side note; if “Love Actually” hits the spot you’re craving in a romantic film, stop reading this list right now. The best era of romantic comedies lands smack-dab at the start of the 21st century, right around when a lot of us undergraduates were firstborn. So if you haven’t explored the wonders of an early 2000s romcom, here’s a guide for you to dip your toes in.
“10 Things I Hate About You”
This 1999 film is the perfect pseudo-enemies-to-lovers choice for those who crave a good Shakespeare movie adaptation. This movie is number one in the top ten overall favorites because of how strongly loveable (and hateable) the characters are. Additionally, Kat Stratford, our strong-willed protagonist, does not have to compromise her values or her stubborn personality to be loved. This is a great reminder around Valentine’s Day that you don’t have to tone yourself down to “be attractive” to others.
“A Cinderella Story”
A classic “Cinderella” story is always a good pick for a Valentine’s Day watch. You can’t get more 2000s than this campy comedy starring Hillary Duff; what teen wouldn’t dream of showing up to the ball (high school dance) to be serenaded by a prince (a high school jock). Spending your time watching this film will not be like waiting for rain in a drought, which Duff iconically categorizes in the movie as “useless and disappointing.”
“She’s the Man”
Quirky deceits, physical humor and witty dialect run rampant in this adaptation of “Twelfth Night.” The comedy in the story is top-notch; misunderstanding after misunderstanding keeps audiences engaged and laughing until the end. Though the movie tries to ignore it, the complicated love triangles (and love squares) our protagonist Viola explores while changing her gender expression provide a breath of fresh air in the sometimes rampant sexism and homophobia portrayed in this era of films.
“The Parent Trap” (1998 version)
Though this movie isn’t always thought of as a romantic comedy, it’s definitely a fresh spin on how old lovers can reconnect (even if they need the help of twin young red-headed Lindsay Lohans). Though the film does run over two hours, the schemes and charm of the daughters are a good choice for Valentine’s Day if you’re looking for a film that’s not too gushy.
“How to Lose a Guy in 10 Days”
A perfect pairing of a woman trying to get a man to break up with her in ten days and a man trying to get a woman to fall in love with him in ten days — nothing could be better. The situational comedy in this film makes for an even more satisfying ending when the characters prevail against the unfortunate situation trying to keep them apart.
“Princess Diaries 2”
Though everyone loves watching young Anne Hathway transform from an ugly duckling to a lady of society in the first film, she shines in finding her true love in the second film of this series. Everyone loves watching Chris Pine transform from a plotting enemy to a trusted lover, and Julie Andrews playing the queen that she already embodies is just the cherry on top.
“The Wedding Planner”
JLo and Matthew McConaughey shine in this unexpected and forbidden romance plot; the chemistry between this career woman and the man whose wedding she’s planning is off the charts. Though it contains a predictable plot, you can’t ask for more out of this timeless comfort where you know the characters will get together in the end.
“Letters to Juliet”
This lesser-known rom-com does not get enough love for how sweet and unique of a story it provides. Though a lot of Shakespeare-related recommendations have been offered in this list, stay with me. The film follows a young girl in Italy who travels across the country trying to reunite old lovers who lost their chance with each other long ago. If you want a heartwarming story with a touch of adventure, this is the one for you.
“To All the Boys I’ve Loved Before”
This movie is an exception to the list because it was made in 2018, but it must be included because of how wonderful of a story it tells. The plot resonated so well with many teen and young adult women because it showed a raw side of navigating your first relationship. Lara Jean showed audiences that it is better to take risks and try out love in the real world rather than hiding behind the pages of romance books; though the road may not always be easy (cough cough the second and third movies), as long as you try, you’ll figure it out.
“My Big Fat Greek Wedding”
If you find yourself thirsting over the hot dad in the “All the Boys I’ve Loved Before” trilogy, travel back in time to 2002 to gawk over the young, long-haired John Corbett. Another classic that stood the test of time because of its resounding message of finding love while staying true to yourself and your culture. The film also doesn’t follow the normal format of love being the main plotline; the story weaves romance into the narrative of Toula and Ian’s regular lives, which is just how love works in the real world.
Honorable Mentions: “Ella Enchanted,” “Maid in Manhattan,” “Sydney White,” “Rosaline” and “Legally Blonde.”
