For some, Valentines Day is a day topped with chocolates and flowers and filled with love and festivity. For others, it’s a day to roll your eyes at tacky decorations and glare at happy couples, but for all, it can be a day to celebrate cinematic history in classic romcoms and chick flicks.
In no exact order, here are my top five movies that are perfect to wrap up another Valentine’s Day.
Clueless
Wealthy and likeable 15-year-old Cher Horowitz (Alicia Silverstone) navigates through high school in Beverly Hills, California as she faces common teenage experiences like giving a new student, Tai (Britany Murphy) a makeover and coaching her to be popular or setting up two single teachers and distracting them enough to boost her grade, and discovering who she wants to be and even who she wants to be with.
Clueless is one of those really sensational feel-good movies that shows while being in love isn’t the most important thing, when you find the right person it can be magical.
As Cher herself says, “Searching for a boy in high school is as useless as searching for meaning in a Pauly Shore movie.”
How to Lose a Guy in 10 Days
Andie Anderson (Kate Hudson) is a committed worker at composure magazine who will do anything to persuade her editor into letting her write about more prominent world topics as opposed to shoes and Pilates. To please her editor, she agrees to write a story where she dates a man for ten days and does the common mistakes that many women do in relationships until he breaks up with her, the only question is who will be the victim to this experiment?
Benjamin Barry (Matthew McConaughey) is in the advertising business and when he bets he can make any woman fall in love with him in ten days for a business deal, two women going for the same deal who know about the composure story set him up with no other than Andie Anderson.
Will Andie drive Benjamin crazy enough to end his business deal? Will Benjamin be able to make Andie fall in love?
How to Lose a Guy in 10 Days puts the com in rom-com, we watch Andie do absurd things to Benjamin like making a family album with AI baby images or becoming best friends with his mother behind his back. With the New York City rush combined with the early 2000’s music and fashion, the movie follows a quick pace with a touch of romance and is definitely a must-watch.
27 Dresses
Always the bridesmaid, never the bride. Jane Nichols (Katherine Heigl) has had a fasciation and love for weddings ever since she was a little girl, the celebration, the dresses, the happiness, all she wants to do is be there for her friends and family on their big day, but when will it be hers?
You may think wedding planning is her job, considering she’s been a crucial part of twenty-seven weddings, but she actually does it completely for fun and has a paying job as an assistant, who she happens to be in love with, a man named George (Edward Burns). However, when her sister comes to town and instantly falls for George, she has no choice but to watch them fall in love and eventually take up the task of planning their wedding.
Throughout the film, Jane has to fight her people-pleasing tendencies and let herself be loved, especially when a journalist, Kevin Doyle (James Marsden) begins showing interest in her.
This is another phenomenal movie set in New York City if you enjoy the city setting and what’s so beautiful about it is how in the face of love everywhere she turns but years of feeling unlovable and putting others needs above her own, we watch Jane finally fall in love and feel the joy she’s watched everyone around her feel her whole life.
This is absolutely the perfect movie for a holiday based on love and relationships if maybe you feel like Jane every once in a while and need a reminder that there is someone for everyone.
10 Things I Hate About You
Intelligent but anti-social high school senior Kat Stratford (Julia Stiles) is the complete opposite of her well-liked bubbly little sister, Bianca Stratford (Larisa Oleynik), but one thing they do share is a dad who decided Bianca was forbidden to date until Kat does. The only problem is, it’s nearly impossible to find a guy to date Kat despite her wits and beauty, and completely impossible to get Kat to agree to it.
With the help of Cameron James (Joseph Gordon-Levitt), a new student who fell head over heels for Bianca, Bianca pulls some strings and finds outcast Patrick Verona (Heath Ledger) to date Kat in exchange for money. Will up-tight Kat finally find herself in love?
Arguably one of the most interesting things about the film is that it’s actually an adaptation of Shakespeare’s “The Taming of the Shrew”. It’s one of the more modernized Shakespeare adaptations so we see the subtle references hidden behind 90’s rock and low-rise jeans. Still, it has clever dialogue and loveable characters and if you’ve seen and enjoyed the other movies on the list, I’m sure you’ll love this classic.
Legally Blonde
Elle Woods (Reese Witherspoon) is well-loved in her sorority and literally has it all. Rich parents, more friends then she can count, endless clothes, bouncy curls, but most importantly for Elle, the love of her life, Warner Huntington III (Matthew Davis).
However, when Warner suddenly decides he needs someone more serious then what he thinks is a ditzy blonde, Elle is determined to win him back.
She decides the only logical way to do this is to go to Harvard Law School and become the kind of serious lawyer Warner wants to marry (Of Course). On the way, she’ll find out what her future holds and how far tireless determination and hard-work can take her.
Elle’s iconic pink outfits and vivacious personality ties the movie together into not just a silly film about a blonde with a credit card but about feminism and defining yourself as much more than the stereotypes labeled by others. This also makes it a great Valentines Day movie and even has a little bit of a love story that unfolds with the plot.
Give a few of these movies a try this Valentines Day if you’re looking for something to watch with your own Valentine (or Galentine) or maybe something to make the day pass by faster if you really hate the holiday. Either way, there’s a great movie or two waiting for you that’s sure to lift your spirits!