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16 Romantic Comedies to Watch on Valentine’s Day

This article is written by a student writer from the Her Campus at UPR chapter.

Valentine’s Day is the perfect day to stay in bed and watch romantic comedies, also it gives you an excuse to cry if you are spending it alone or just cry because c’mon who doesn’t cry watching Love Actually? If you are spending the night with your loved one, cuddle up and get ready; for the lonely hearts you’ll need some chocolate boxes and Kleenex. Go grab some popcorn, a blanket and enjoy!

 

1. When Harry Met Sally (1989)

 

Starring: Billy Crystal and Meg Ryan

What it’s about? Harry and Sally met when she gives him a ride to New York after both graduate from the University of Chicago. They part ways, deciding that a man and woman can’t simply be friends without romantic feelings getting in the way. They run into each other several times over the years, always facing the same question: Are they just friends, or is their relationship something more?

Favorite Quote: “I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.”

 

2. Breakfast at Tiffany’s (1961)

 

Starring: Audrey Hepburn and George Peppard

What it’s about? A struggling writer (Peppard) moves into an apartment building on Manhattan’s swanky Upper East Side and becomes intrigued by his pretty and quirky socialite neighbor (Hepburn).

Favorite Quote: “You know what’s wrong with you, Miss Whoever-you-are? You’re a chicken, you’ve got no guts. You’re afraid to stick out your chin and say, ‘Okay, life’s a fact, people do fall in love, people do belong to each other, because that’s the only chance anybody’s got for real happiness.” 

 

3. Love Actually (2003)

 

Starring: Hugh Grant, Liam Neeson, Colin Firth, Laura Linney, Emma Thompson and a whole lot of famous people.

What it’s about? During the month before Christmas the movie follows 8 couples, all loosely interconnected with each other, as they fall in and out of love, some finding themselves with the wrong people and others still searching for the right people.

Favorite Quote: “It seems to me that love is everywhere. Often, it’s not particularly dignified or newsworthy, but it’s always there, fathers and sons, mothers and daughters, husbands and wives, boyfriends, girlfriends, old friends…If you look for it, I’ve got a sneaky feeling you’ll find that love actually is all around.”

 

4. 10 Things I Hate About You (1999)

 

Starring: Julia Styles and Heath Ledger

What it’s about? Adapted from William Shakespeare’s play “The Taming of the Shrew”. A new kid must find a guy to date the meanest girl in school, the older sister of the girl he has a crush on, who cannot date until her older sister does.

Favorite Quote: I hate the way you talk to me, and the way you cut your hair. I hate the way you drive my car, I hate it when you stare. I hate your big, dumb combat boots and the way you read my mind. I hate you so much it makes me sick — It even makes me rhyme. I hate the way you’re always right. I hate it when you lie. I hate it when you make me laugh — Even worse when you make me cry. I hate it when you’re not around. And the fact that you didn’t call. But mostly I hate the way I don’t hate you — Not even close, not even a little bit, not even at all.”

 

 

5. 27 Dresses (2008)

 

Starring: Katherine Heigl and James Marsden

What it’s about? After serving as a bridesmaid 27 times, a young woman wrestles with the idea of standing by her sister’s side as her sibling marries the man she’s secretly in love with.

Favorite Quote:Love is patient. Love is kind. Love means slowly losing your mind.” 

 

6. He’s Just Not That Into You (2009)

Starring: Scarlett Johansson, Jennifer Aniston, Ginnifer Goodwin, Drew Barrymore, Ben Affleck, Justin Long, Bradley Cooper

What it’s about? Baltimore-based friends and lovers, all in their 20s and 30s, try to navigate their way through the complexities of modern relationships.

 Favorite Quote: “Maybe a happy ending doesn’t include a guy, maybe it’s you, on your own picking up the pieces and starting over, freeing yourself up for something better in the future. Maybe the happy ending is just moving on.”  AND AND AND

“I love you so much. So much. And I wanna make you happy. I need to make you happy for me to have a shot at being happy.”

 

 

7. How To Lose a Guy in 10 Days (2003)

 

Starring: Matthew McConaughey and Kate Hudson

What it’s about? Benjamin an advertising executive competing with two female co-workers for a major campaign for a diamond merchant. He cuts a deal with his competitors that the account is his if he can make a woman of their choice fall in love with him in 10 days. In comes Andie, who, in turn, is writing a story on how to lose a guy in 10 days as a bet with her boss to be allowed to write more substantial stories. With a hidden agenda in each camp, will either party be able to complete their mission?

Favorite Quote: “You can’t lose something you never had.”

 

 

8. 13 Going On 30 (2004)

Starring: Jennifer Garner and Mark Ruffalo

What it’s about? When a geeky teen’s birthday party goes awry and she makes a wish that she could be 30, she wakes up to discover she’s flash-forwarded 17 years.

Favorite Quote: “I think all of us wanna feel something that we’ve forgotten or turned our backs on. Because maybe we didn’t realize how much we were leaving behind.”

 

9. The Five Year Engagement (2012)

Starring: Emily Blunt and Jason Segel

What it’s about? One year after meeting, Tom proposes to his girlfriend, Violet, but unexpected events keep tripping them up as they look to walk down the aisle together.

Favorite Quote: “The first important thing to remember about marriage is that it requires commitment. The second is that so does insanity.”

 

 

10. Say Anything (1989)

Starring: John Cusack and Ione Skye

What it’s about? High school senior Lloyd Dobler wants nothing more than to go out with beautiful and intelligent Diane Court. Lloyd attempts to win her heart over the objections of her over-protective father before Diane leaves for a scholarship in England.

Favorite Quote: “I gave her my heart. She gave me a pen.”

 

 

11. Crazy, Stupid, Love (2011)

Starring: Ryan Gosling, Emma Stone, Julianne Moore, Steve Carell and whole other bunch of famous people.

What it’s about? A middle-aged husband’s life changes dramatically when his wife asks him for a divorce. He seeks to rediscover his manhood with the help of a newfound friend, Jacob, learning to pick up girls at bars.

Favorite Quote: “I will never stop trying, because when you find the one…you never give up.”

 

12. There’s Something About Mary (1998)

Starring: Cameron Diaz and Ben Stiller

What it’s about? A man gets a chance to meet up with his dream girl from high school, even though his date with her back then was a complete disaster.

Favorite Quote: “Love isn’t about money, or social standing or age. It’s about two people connecting.”

 

13. The Ugly Truth (2009)

Starring: Gerald Butler and Katherine Heigl

What it’s about? A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever ploys, however, lead to an unexpected result.

Favorite Quote:  I just told you that I loved you and all you heard was “psycho.” Well you’re the definition of neurotic.”

 

14. When in Rome (2010)

Starring: Kristen Bell and Josh Duhamel

What it’s about? Beth is a young, ambitious New Yorker who is completely unlucky in love. However, on a whirlwind trip to Rome, she impulsively steals some coins from a reputed fountain of love, and is then aggressively pursued by a band of suitors.

Favorite Quote: “It’s like, I meet a guy, and I think it’s great and anyone else would just be thinking about how much greater it’s going to get. And I’m constantly waiting for the other shoe to drop.”

 

15. Leap Year (2010)

 

Starring: Amy Adams and Matthew Goode

What it’s about? A woman who has an elaborate scheme to propose to her boyfriend on Leap Day, an Irish tradition which occurs every time the date February 29 rolls around, faces a major setback when bad weather threatens to derail her planned trip to Dublin. With the help of an innkeeper, however, her cross-country odyssey just might result in her getting engaged.

Favorite Quote: “When my 60 seconds came around I realized I had everything I ever wanted… but nothing I really needed. And I think what I need is here. And I came all this way to see if you maybe think so too. If you do, well… I don’t really have plans past that, which is new for me…I propose we not make plans, i propose we give this thing a chance and let it work out how it works out. so what do you say, do you wanna not make plans with me?”

 

16. Clueless (1995)

Starring: Alicia Silverstone and Paul Rudd

What it’s about? A rich high school student tries to boost a new pupil’s popularity, but reckons without affairs of the heart getting in the way. It’s based on Jane Austen’s 1815 Emma but loosely adapted.

Favorite Quote: “You are a virgin who can’t drive.”…sorry I had to.

 

 

 

Gabriela Cirilo is a Marketing student at the University of Puerto Rico, Rio Piedras campus. She's currently an intern at the IT company and consulting firm Wovenware Inc. Gabriela is a social media and movie addict. She enjoys reading, swimming and listening to new music. Also she loves fashion...and history.