FILM: 100+ Romantic Films (by Category)

In honor of V-Day, I present a slew of romantic comedies and dramas that celebrate loves ups and downs: 

For—what I like to call—the butterfly effect, where a geeky or bland girl transforms into a beautiful and/or confident woman, mixed with a little lovin', watch these:
• Bridget Jones' Diary: A woman uses a diary to try to improve herself while looking for love.
• Can't Buy Me Love: A nerd blackmails the most popular girl in school into helping him become popular.
• Dirty Dancing: A conservative rich girl falls in love with her hot and older dance instructor, and comes out of her shell.
• Drive Me Crazy: A teenage social climber tries to get the hottest guy in school to take notice by using her childhood best friend to make him jealous.
• Ever After: The story of Cinderella if she weren't that much of a damsel in distress.
• Milk Money: A prostitute steals her pimp's money and runs away to suburbia with a few underaged boys who tried to use her services.
• My Big Fat Greek Wedding: A woman finds the man of her dreams, and has to figure out a way to keep him in spite of her meddlesome family.
• Never Been Kissed: A copywriter who goes undercover at a high school to find some newsworthy dirt.
• Pretty Woman: A hooker with a heart-of-gold turns a rich workaholic into a hopeless romantic.
• She's All That: The king of the jocks makes a bet with his best bud that he can turn any loser into the prom queen.
• Sixteen Candles: A teenage girl's family forgets her birthday so she tries to salvage the night by going to a school dance and working up the courage to ask out the hottest guy in school.
• True Lies: A housewife tries to spice up her life with an affair. When her spy husband figures it out, he uses his agency to give her the adventure she obviously desires. The charade gets out of hand when very real terrorists kidnap them and plot an attack in America.
• The Truth About Cats & Dogs: A radio personality who gives pet advice asks her neighbor to pretend to be her to snag a guy.
• The Wedding Planner: A wedding planner inadvertently falls for the groom.

To watch men fall all over themselves to impress a girl or get over an ex, and find the courage to risk their hearts for a girl who is either out of their league or a potentially refreshing rebound, watch:
• (500) Days of Summer: It's a love story told out of order. You may know how it ends from the start, but it's how he fell in love and why he loves her that's the real story. Delve into one man's psyche as he learns the difference between infatuation and passion.
• Career Opportunities: A super hot spoiled rich girl seduces her father's store employee when they get stuck in his department store overnight.
• Definitely, Maybe: If you like mysteries, you might like trying to figure out which girl (Rachel Weisz, Elizabeth Banks, or Isla Fisher) Ryan Reynolds' character ends up with as he tells his daughter the story of how he met her mother.
• Forgetting Sarah Marshall: A struggling musician gets dumped by his actress girlfriend and goes on the vacation they planned together by himself to sulk and mope in peace. Possibly one of the funniest breakup films sugar-coated with a love story in the last inning.
• Ghost of Girlfriends Past: Yes, while it's true that Matthew McConaughey is criminally dressed for 95% of this film, it's also a new side to him. He's not the sweet, caring, misunderstood Romeo. He's the obnoxious, tail-chasing, pig-headed Casanova. Who could tame him better than the girl next door?...with a little help from a few haunting spirits.
• Hitch: A businessman hires a dating consultant to help him get the girl of his dreams.
• Nick & Norah's Infinite Playlist: In the course of one night, two music lovers in search of their favorite underground band fall in love.
• She's Out of My League: While Jay Baruchel manages to still have a backbone in this film, he presents the interesting and relatively mature perspective of how insecure a guy can get in a relationship. So for once, it's the guy's insecurities that stall a relationship.
• The Sorcerer's Apprentice: A young scientist accidentally frees two warring wizards, and as he trains with one to destroy the other, he works up the courage to win the heart of his childhood crush.
• Take Me Home Tonight: A stunted recent college grad goes to his sister's boyfriend's party to finally make a move on his high school crush.
• The Wedding Singer: Two engaged people figure out they're engaged to the wrong people.
• Youth in Revolt: A geeky virgin sets out to lose his virginity to his dream girl with a little help form his bad boy alter ego.
• Zookeeper: A zoo full of animals start talking to their zookeeper to help win back his superficial golddigger of an ex.

If love-hate relationships are your personal fave:
• 10 Things I Hate About You: Julia Stiles vs. Heath Ledger
• 27 Dresses: Katherine Heigl vs. James Marsden
• The Bounty Hunter: Jennifer Aniston vs. Gerard Butler
• Clueless: Alicia Silverstone vs. Paul Rudd
• Confessions of a Shopaholic: Isla Fisher vs. Hugh Dancy
• The Cutting Edge: Moira Kelly vs. D.B. Sweeney 
• Dedication: Mandy Moore vs. Billy Crudup
• Excess Baggage: Alicia Silverstone vs. Benicio Del Toro
• Flipped: Madeline Carroll vs. Callan McAuliffe
• From Nada to Prada: Alexa Vega vs. Wilmer Valderramma
• Just Like Heaven: Reese Witherspoon vs. Mark Ruffalo
• Leap Year: Amy Adams vs. Matthew Goode
• Letters to Juliet: Amanda Seyfried vs. Christopher Egan
• Life As We Know It: Katherine Heigl vs. Josh Duhamel
• Mr. & Mrs. Smith: Angelina Jolie vs. Brad Pitt 
• My Life in Ruins: Nia Vardalos vs. Alexis Georgoulis
• New in Town: Renee Zellweger vs. Harry Connick Jr.
• One Fine Day: Michelle Pfeiffer vs. George Clooney
• Overboard: Goldie Hawn vs. Kurt Russell
• Princess Diaries: Royal Engagement: Anne Hathaway vs. Chris Pine
• The Proposal: Sandra Bullock vs. Ryan Reynolds
• Sweet Home Alabama: Reese Witherspoon vs. Josh Lucas
• The Ugly Truth: Katherine Heigl vs. Gerard Butler
• What Happens in Vegas: Cameron Diaz vs. Ashton Kutcher

If you want to cry your eyes out and feel a faint tug at the heart strings:
• 50 First Dates: A man meets a woman who's life is like Groundhog's Day. Her amnesia resets every morning and she lives the same day every day, until she meets a guy who falls in love with her and endeavors to help her live her life instead of repeat it.
• Blue Valentine: A married couple charts their evolution over a span of years by cross-cutting between time periods.
• Brokeback Mountain: An undeniable forbidden love between two cowboys, who discovered something in each other they didn't knew could exist.
• Country Song: Two country singers are forced to choose between fame and love.
• Dear John: A soldier falls for a college student while he's home on leave.
• Eat Pray Love: A newly divorced writer goes on a trip through Europe and Asia, and finds love in the most unexpected way.
• Going the Distance: A guy and a girl try to keep their relationship light and noncommittal, but the further they are from each other the more tensions rise.
• The Last Song: A rebellious girl is sent to a Southern beach town for the summer to stay with her father, and falls in love with a local boy who helps her through a difficult time.
• Like Crazy: Two young lovers are torn apart by immigration, and are forced to continue their romance long-distance.
• Love and Other Drugs: A Viagra-hawking playboy pharmaceutical rep falls for a Parkinsons-stricken woman.
• The Notebook: An old man tells his Alzheimer's-stricken wife the story of how they fell in love.
• One Day: After spending the night together on the night of their college graduation, two friends decide to meet every year on that same day to see where they are in their lives.
• P.S. I Love You: A woman reads the love letters her husband left her after he dies, and learns to move on with his consoling words.
• Slumdog Millionaire: A young guy goes above and beyond to win over his childhood sweetheart by going on India's "Who Wants to Be a Millionaire?" to prove he can give her everything they never had.
• The Time Traveler's Wife: Two people fall in love literally at different points in time, and try to make an unorthodox long-distance relationship work.
• Up: This isn't so much about a current love story, but about its affect long after the relationship has ended. It's about what love makes you do.
• Water for Elephants: A veterinary student abandons his studies after his parents are killed and joins a traveling circus as their vet, quickly falling for the Ringmaster's beautiful acrobat.

If you're a fan of blind love, where two people fall for each other without ever having seen each other's faces or learned each other's true identities/personalities, or love through deception: 
• 17 Again: A man who regrets being a young teen father gets a second chance to be a basketball pro.
• Arthur: A wealthy playboy tries to woo an uninterested middle class woman, and pulls out all the stops.
• The Back-Up Plan: A single woman too impatient to wait for the one decides to undergo invitro, then meets previously mentioned "one" and has to rethink her idea of happily ever after.
• Bad Teacher: A golddigger tries to seduce an heir to a fortune moonlighting as a substitute teacher.
• The Brothers Bloom: A con man and his brother cons an heiress who inevitably (and accidentally) cons him into falling for her.
• Coming to America: A prince goes to America to find a woman who will love him for who he is and not how much money he has.
• Easy A: A virgin let's one lie snowball until she's branded the skankiest girl in school. Instead of crawling into a hole, however, she takes advantage of all the attention, all the while unaware that there's still one guy who sees her for who she really is.
• Hannah Montana: The Movie: It's the story of a girl who has to learn to love herself, while she falls for someone who already does.
• Head Over Heels: An art restorer suspects her hot neighbor might be a serial killer.
• How to Lose a Guy in 10 Days: A journalist gets an assignment where she has to get a guy to dump her and the guy she chooses just so happens to have made a bet where he can get any woman to fall in love with him.
• Ira & Abby: A man quickly falls in love with a woman he meets, marries her, and then discovers that she might be in love with being in love.
• Just One of the Guys: A beautiful popular girl wants to win a journalism internship, but feels her looks have clouded her professor's judgement, so she switch schools and dresses up like a guy in search of a story that'll prove she has what it takes.
• Just Wright: Guys rarely fall for the big girl, because they're deluded into believing beauty lasts forever. This film entertains the idea that maybe guys should shoot for the girl they have the most in common with. What a concept!
• Killers: A lonely woman falls in love with an assassin, who gives up the life for her, only to later discover that almost everyone in their life is a planted assassin looking to scrub out her beau.
• Knight & Day: A spy trying to protect a brilliant scientist accidentally involves an unsuspecting woman, and is forced to protect them both until he can stop an enterprising double agent.
• Monte Carlo: A high school grad gets mistaken for an heiress while she's backpacking through Europe. She has to fool the heiress family, the press, and her would-be suitor.
• The Other End of the Line: A customer service rep based in India falls in love with one of her customers over the phone.
• Penelope: A young woman is cursed with a pig snout for a nose because of her ancestors' indiscretions. The only way her beauty will be restored is if she finds someone to love her for who she is and not what she looks like.
• She's the Man: A teenage soccer player transfers to her twin brother's school to impersonate him while he's away so that she can prove that she's just as good at soccer as boys are.
• Shrek Forever After: The jolly green ogre is overwhelmed by domesticated family life and makes a deal with Rumpelstiltskin that erases his heroism, forcing him to win Fiona's heart all over again.
• Tangled: It's the story of Rapunzel, if she were a little more proactive in saving herself and if her hero were a thief.
• The Tourist: A wanted crimimal's girlfriend leads the FBI on a wild goose chase when she tricks a school teacher into impersonating her never-before-seen lover.
• The Wedding Date: Even though he's playing a professional male escort, Dermot Mulroney is ultra dreamy in this film about a woman (Debra Messing) so insecure about going to her little sister's wedding and seeing her ex-fiancee that she hires some extra "help."
• While You Were Sleeping: A woman helps a man get medical attention and the hospital mistakes her for his fiancee, leading his family to embrace, except for his suspicious brother.
• Wild Target: A veteran hitman is sent to kill an art thief but falls in love with her instead, and sets out to protect her.
• You've Got Mail: Two competing bookstore owners unknowingly fall in love online.

If you think that true love blossoms from friendship, then snuggle up with your bff-soon-to-be-bf, and watch:
• 13 Going on 30: A thirteen year old girl wakes up thirty years old and learns what she turned into after ditching her best guy-friend to join the popular girls.
• Date Night: Technically they're not friends, they're a married couple, but it's through their rediscovery of their friendship that they rekindle their love.
• Easy Virtue: A young British man brings his rebellious American wife home to his stuffy family.
• Friends with Benefits: Two good friends decide to use each other for sex because they're tired of the demanding and disappointing results of relationships.
• How Do You Know: A soon-to-be indicted lawyer falls for a female baseball pro who's cut from her team and spirals into self-doubt when she's relegated to being her baseball pro boyfriend's arm candy.
• I Love You, Man: Alright so this isn't really a rom-com, but it is about the love between friends.
• Just Go With It: A plastic surgeon who uses a wedding ring and a sob story to guilt women into having sex with him believes he's met the perfect girl, and ropes his receptionist into helping him pretend that he's getting divorced.
• Made of Honor: A playboy is forced to participate in his best friend's wedding and suddenly realizes she's the girl of his dreams.
• No Strings Attached: Two friends decide to add sex to their relationship without any emotional commitment.
• Paper Heart: It's technically a documentary about how true love may not really exist, but if you think about it, at least she's trying to prove herself wrong.
• Post Grad: An unemployed recent grad moves back in with her family while she tries to figure out her life, with the help of her doting guy friend. • When Harry Met Sally: Two best friends who cultivate a friendship over many years are afraid sex will ruin their relationship.
• Something Borrowed: Girl falls for classmate. Girl's bff steals him. Girl decides to steal him back.
• The Switch: A guy whose best friends opts for invitro drunkenly switches out his sperm for her donor's and has to face the consequences ten years later when she returns to town with a kid who looks and acts just like him.
• What's Your Number?: An unemployed promiscuous bachelorette decides to reconsider all of her ex-boyfriends so she won't exceed the "appropriate" amount of men women are socially allowed to sleep with. She enlists her playboy neighbor, who's really good at finding people due to his law enforcement connections, to help her find all of her exes in exchange for helping him get rid of his one-night stands.

For ensemble casts with an array of romantic plotlines, watch:
• Crazy Stupid Love: A cuckolded husband tries to get back into the dating scene with the help of a handsome Lothario, who has a few lessons to learn of his own, while his son tries to win the heart of his babysitter. Three love stories. Three different generations. Three different levels of love: first love, young love, and married love.
• He's Just Not that Into You: Several love stories examining modern romance.
• Jumping the Broom: A couple from opposite sides of the tracks decide to get married despite their mothers' disapproval. During the pre-wedding festivities, unlikely pairing flourish.
• Love Actually: So many British love stories beautifully told.
• New Years' Eve: Several different type of love stories all climaxing on the most magical and expectation-heavy day of the year.
• New York, I Love You: Vignettes about the different types of love and the different reasons to love in New York.
• Paris je t'aime: Vignettes about the different types of love in Paris.
• Prom: A group of teenagers get ready for their high school prom, exploring the pressures of getting a date, not ditching a friend, not getting asked, and much more.
• Valentine's Day: Love stories that happen on Cupid's busiest day of the year.

For roadtrips to love:
• Away We Go: Two soon-to-be parents try to find a place to settle down, while they figure out whether they should have a traditional family or just one that's filled with love.
• Broken English: A woman discovers herself while visiting Paris to find the guy she thinks might be the one.
• Eurotrip: A college guy goes to Europe with his friends to meet his hot pen pal.
• The Sweetest Thing: A commitment-phobe recruits her best friend to go on a road trip to find the guy she clicked with at a bar.
• When in Rome: An ambitious museum curator drunkenly steals coins from a Roman fountain, stealing the hearts of the men who made wishes with the coin, and making them obsessed with her. When she falls for a guy, she worries that he might be magically possessed as well.

For supernatural, fairytale, or alien romances:
• Adjustment Bureau: A politician and a ballerina must decide if they'll defy The Fates to preserve their love, or follow their professional destinies.
• Avatar: A paraplegic Marine, recruited to infiltrate an alien species and find a secret resource, falls in love with the warrior princess, forced to teach him about their people.
• Beastly: An obnoxious popular teenager gets turned into a scarred and tattooed beast by his witchy vengeful classmate and forced to find true love before it's too late.
• Enchanted: An evil queen banishes a princess from their animated fairytale to the real world so she won't marry her son, and she must find a new Prince Charming to help her get back.
• Let Me In: A human boy falls in love with the vampire girl who lives next door. Both suffering from debilitating loneliness, they find comfort in each other.
• Practical Magic: Two witch sisters must break the love curse that lies on the women of her family.
• Red Riding Hood: A wolf terrorizes a small village and everyone's a suspect. A young woman must decide who to trust with heart. Will it be the orphan wood cutter or the wealthy warrior?
• Simply Irresistible: A restaurant owner seduces a department store executive with her magical food.
• Twilight: A human and a vampire fall in love, and they must fight against all odds to stay together.