Top 14 Romantic Comedies to Watch This Valentine’s Day

With another Valentine‘s Day coming up, it’s time to get in the spirit the only way we know how, and that is by watching Romantic Comedies while eating ice cream out of the tub and drinking wine out of the bottle.

Here are 14, yes 14 because you can’t forget that Valentine’s Day is on February 14th, Romantic Comedies that are the most elite, ranked  to best, that you can watch alone, with your significant other, or with a friend (human or pet).

14. Something Borrowed (2011)

Something Borrowed starring Kate Hudson, Ginnifer Goodwin, John Krasinski, and Colin Egglesfield, adapted from the Emily Giffin novel of the same name, is about two best friends living in New York City. Darcy (Hudson) happens to be getting married to Rachel’s (Goodwin) long- time law school crush Dex (Egglesfield), when Dex and Rachel start an affair that could ruin Rachel and Darcy’s lifelong friendship.

This movie definitely deserves the title of a “rom-com” as John Krasinski, who plays Rachel’s confidant, adds his dry and abrupt humor to the complex relationships of the film. Although the movie includes complicated decisions that the characters must make, the tone is still light-hearted and very much enjoyable. Colin Egglesfield’s character Dex, is a man we all want, as he treats Rachel like she is the only person in the world, to get cliche. (Even though he didn’t break off the wedding until the last second but let’s not talk about that because men are not perfect—not even close)

If I were to rate this rom-com, I would give it 3.5/5 hearts (for love) because although in the end, Rachel gets what she’s wanted since her time in law school, she is very much flawed because had she just spoken up for what she wanted in the first place, Darcy never would have gotten together with Dex.

13. How to Lose A Guy in 10 Days (2003)

Andie Anderson (Kate Hudson) is an intelligent advice columnist working at a gossip magazine, who wants to push her writing boundaries into topics with more depth, but only after if she writes about how to get a man to leave you in ten days. Ben (Matthew McConaughey), a so-called makes a bet with his friends that he can make any girl fall in love with him. Enter: Andie and you get a hilarious duo that is also like a ticking time bomb because eventually, they are bound to find out about both of their challenges.

I love this movie because at first, Andie takes the advice from her heartbroken friend who does everything that makes a guy want to leave; she’s clingy, takes possession over his apartment, gives his lower body part pet names, takes him to girly concerts (instead of basketball games), makes him go eat vegan, coddles him, etc. All of this, Andie does, and all of this, Ben stays for, which makes Andie aggravated. But eventually, their real personalities start to peak out, and so does their fondness for each other.

I’m giving this 4/5 hearts because the humor is unmatched as it pokes fun of clingy, annoying girlfriends, but the undeniable chemistry that Kate Hudson and Matthew McConaughey have is unmatched, and therefore, make a great match on any screen they share.

12. The Big Sick (2017)

Kumail (Kumail Nanijani) and Emily (Zoe Kazan) meet at one of Kumail’s stand-up shows. As their relationship becomes more involved, Emily comes down with a chronic disease that lands her in a coma, but it doesn’t stop Kumail from coming to the hospital to take care of her with her parents (Ray Romano and Holly Hunter), who he forms a bond with.

This film is a little less funny than the rest, but I think it deserves to be included because it’s charming, and while the tone of the movie is somewhat sad, it still maintains the light-hearted humor of Kumail Nanijani while also retaining an aspect of reality that isn’t packed with fantastical and impractical expectations that normal romance movies contain. the film is also somewhat underrated as I haven’t heard it being praised as much as the others, but just because it isn’t quite as well-known, doesn’t mean it isn’t as wonderful.

I’m giving it 4/5 hearts because it deals with a lot of real issues that are unpredictable in reality, and it shows that just because people come from different cultures, doesn’t mean they can’t give a relationship a try, especially if the person shows up for the other everyday when one’s in a coma.

11. Clueless (1995)

This movie is popular for a reason. Who doesn’t love a 90’s high school movie with Paul Rudd, Alicia Silverstone, and Brittany Murphy? Cher (Alicia Silverstone) is the typical daughter of a rich man; smart, successful, and popular all while being a totally fabulous dresser. While trying to set up the new girl Tai (Britanny Murphy) with another popular boy, Cher has boy problems of her own as she falls for her college- age step brother Josh (Paul Rudd).

If someone asked me to describe a 90’s high school experience with one movie, this is the one I’d pick. The music, outfits, and the cast seem to be the perfect representation of what it was like to be in high school in the 90’s. Secretly, I think all girls want to end up with someone like Josh; funny, smart, charming, and a bit nerdy. It wouldn’t hurt if we had a guy that looked like him either. This romantic comedy, although nostalgic for millennials, will always be a cult classic and personally, I think every generation after will enjoy it as well.

4.5/5 hearts

10. 13 Going on 30 (2004)

This is one of those movies that I would watch over and over as a kid, and would probably consider it as one of my favorite movies. Jenna Rink (Christa B. Allen) is best friends with Matt (Sean Marquette), but wants an in with the popular kids, but at her birthday party she is transformed, with the help of magic dust, into her 30 year- old- self (Jennifer Garner) living her dream in Mannhattan. She resorts to contacting Matt (Mark Ruffalo) to tell her about her life after 13, and after rekindling their friendship after not speaking for years, they find their friendship isn’t quite the same as it used to be.

The movie is so innocent, and since Jenna is 13 in a 30 year-old body, retains the innocence throughout, which is not often seen in romantic comedies. Just like Jenna’s character, the movie is filled with life and laughter, and “silliness”, and while everyone around her is at first confused, eventually, they take their guard down and don’t take life as seriously as they once did. I still love this movie because it’s inspiring in a way, because just because you grow up, does not mean that life should be boring and gray.

I give this movie 4.7/ 5 because of the joyous aspect of it. If I need a pick-me-up, I always go to this movie because it always makes me feel better, and it also has an amazing soundtrack.

9. My Best Friend’s Wedding (1997)

This movie is what I think of when I hear I Say a Little Prayer For You by Dionne Warwick (or Aretha Franklin). That part is probably the best part of the whole movie because it makes you wanna break out in song with a whole restaurant too. Julianne Potter (Julia Roberts) and Michael O’Neal (Dermot Mulroney) are childhood best friends who made a pact to get married they they were both single at 28, but Michael tells her that he is marrying Kimberly (Cameron Diaz), even though Julianne wanted to confess her love to him, and is convinced she can win him back.

At first I didn’t particularly love this movie because of course (spoiler) Julia Roberts does not get the guy, but it grew on me because her gay friend George (Rupert Everett) pretends that they are together to originally make Michael jealous, but he pretty much makes this movie as he tries in every way to make Julianne not be heartbroken over Michael, because at the end, it is not worth chasing him, literally and figuratively. It also grew on me because it’s a reminder that you can’t get the guy (or whatever you want) all the time, which is mostly the case in reality, but in movies, it almost never shows that, and if they go through a lot of hurdles to get what they want, it’s expected that they do.

This movie gets 4.7/ 5 also because it’s not quite the perfect combination of romance and comedy, as it is more funny than romantic, but it still deserves the title of a rom-com because the audience is led to believe that Julianne will get what she wants in the end.

8. 10 Things I Hate About You (1999)

This is another cult classic; another teenage dream movie that all girls at the high school and college age swoon over. Kat Stratford (Julia Stiles) is an outcast in her high school. She’s smart but not well liked by everyone, including boys, which is quite unfortunate for her younger sister Bianca (Larisa Oleynik) who cannot date until Kat does. She is set up with Patrick Verona (Heath Ledger *swoons*), who is paid to take her out. It all changes when he actually falls for her.

If you don’t fall for his Australian accent from the time he walks into Ms. Perky’s (Allison Janney) office, then you are sure to fall for his idea of a date at a paintball park, where they share a hay-filled messy kiss, or tries to serenade Kat with his rendition of Can’t Take My Eyes Off You by Frankie Valli. This movie is also a movie that I would put under the definition of high school in the 90’s just because it’s that iconic. It’s always great to see a male falling for a woman because it gives us ladies a bit of hope, that maybe men aren’t that bad after all.

I give this movie 4.7/5 purely because of Heath Ledger’s charm (and his smile), but also because the comedic side of the movie is quite unmatched as it’s more of an embarrassing kind of humor as it pokes fun of most things like popularity and being “normal” in high school.

7. Something’s Gotta Give (2003)

Jack Nicholson stars as Harry Sanborn, a rich womanizer who visits the Hamptons home of his much younger girlfriend Marin’s (Amanda Peet) mother, Erica Barry (Diane Keaton), who is also staying there for the weekend, writing her latest play. At first, Erica is not too keen on Harry and her daughter’s relationship, but after Harry suffers a heart attack the same weekend, he is put on bed rest and it changes everything when Harry and Erica fall for each other.

Jack Nicholson once again proves that he can play a charming, yet narcissistic man who realizes that his life isn’t quite making him happy anymore because he found something better. The timing, phrasing, and honesty in his words make this movie what it’s supposed to be: down right funny. The kind of funny that makes you think that you actually did pee in your pants this time. This movie could be watched by most everyone, young adult and…a lot less young adult. Diane Keaton lives in anyone’s dream Hampton’s house, and Jack Nicholson tries to climb a flight of stairs (which makes sense if you’ve seen the movie). This movie is probably best described as “life is funny that way”, because it’s the perfect marriage between real life stories of love, and sometimes plain old goofiness.

I give this movie a 4.8/ 5 just because it’s irreverence makes it something that could be watched twenty times and it would still be funny.

6. The Princess Bride (1987)

This is definitely an oldie but a goodie. Buttercup and Westley are two young lovers who are parted, and then a few years later, come together again, unknowingly, to defeat the evils of Prince Humperdinck, as Buttercup is chosen to be his Princess Bride. Buttercup is kidnapped by pirates to start a war against nations, and Westley, who is now Dread Pirate Roberts, saves her.

This is one of those movies that I would watch when I was home sick from school, so I have a nostalgic attachment to it, but I also think I might be drawn to movies with satire and dry humor because it surely has plenty of that. It has pirates, princesses, sword fights, Mandy Patinkin, and “trueee looove”. No seriously, if you’ve never seen this movie, I would consider rethinking your entire existence because there are so many quotable moments in there that, if you were friends with me, you wouldn’t understand a lot what I say.

This movie deserves 4.8/5 hearts because there are just too many people in this movie that make it the classic that it is, lots of quotable lines, and the romantic heroism that we all deserve to see in a live-action movie. It’s a fairy tale for grown-ups that’s appropriate for all ages.

5. My Big Fat Greek Wedding (2002)

Toula (Nia Vardalos) works in her family’s Greek restaurant when she meets Ian Miller (John Corbett), who is not Greek, but she is smitten for immediately. At first, she is meek and dowdy, but decides to change her look and take a class to learn more about computers. When Ian sees her working one day, he asks her out, start dating in secret because of her strict family traditions, and eventually fall in love. Despite her family’s disapproval of Toula dating a non- Greek, Ian proposes, and thus, his journey with Toula’s family begins.

There are also a lot of quotable lines in this movie. “Put a little windex on it” has become a joke for many families, including mine. One of the best scenes in the movie, if not the best, is when Ian’s parents join Toula and their son, to meet Toula’s family, which they thought would be a quiet meal, but to their surprise, the whole Portokalos klan, including cousins, aunts, uncles, and lots of people with the name Nick. This movie is another movie that is incredibly realistic as any outcast of a big, loud family would react the same way as the Millers do, which is to be a bit overwhelmed, and then to join in on the fun, because it simply is better that way.

I give this movie a 4.8/5 because it has all of the aspects of a good rom-com; easy to watch, envious of the main character, and hilarious in the most natural way

4. Crazy Stupid Love (2011)

Two words: David. Lindhagen. Cal (Steve Carrell) and his wife Emily (Julianne Moore) live a normal life with three kids and a nice home, but it all changes when Emily confesses that she had an affair with someone from work, (Enter: David Lindhagen (played by Kevin Bacon)) and asks Cal for a divorce. He moves out of the family home into an apartment and falls into a depression, but when he meets Jacob, a local lady’s man, Jacob takes him under his wing and completely changes his look. Meanwhile, Jacob meets Hannah, (Emma Stone), a law student, after she breaks up with her boyfriend, and immediately goes home with him, staying the whole night talking with him. What Jacob doesn’t know, is that Hannah is Cal and Emily’s daughter.

Crazy Stupid Love is one of those movies that connects, at the last second, every character in the whole movie, which makes the entire thing better and more funny. Every character holds their own in the comedic half of this rom-com, as everyone pines after their love interest, who may or may not also love them too. Some love interests make sense, some don’t, but the funniest part in the movie involves all of the male roles. Yes, that includes David Lindhagen. Just trust me, the irony and serendipity of the film makes it twice as funny as the dialogue itself.

I think the movie deserves more recognition, and therefore, I give this movie a 4.8/5  since the amount of stars in the movie really makes the movie fun as well as easy to watch.

3. 50 First Dates (2004)

This is the best movie that Adam Sandler has made by a landslide. Sandler plays Henry Roth, a veterinarian who works at a Hawaiian aquarium meets a girl at a local restaurant, Lucy Whitmore (Drew Barrymore), but what he doesn’t know is that she suffers from memory loss from a car accident and therefore, lives the same day everyday. After many failed attempts, he wins her over everyday, and with the help of his friend Ula (Rob Schneider), he creates a video introducing himself and what happened to her that she cannot remember anything that happens after that day, and eventually she starts to journal about him, so she can remember him. Everyday, she falls in love with him again, and everyday, Henry falls in love with her more.

With a great cast of Sandler himself, Rob Schneider, Sean Astin, Maya Rudolph, and Dan Akroyd, this movie was bound to be Saturday Night Live alumni gold. The love story makes it better, in my opinion, than any Adam Sandler movie because Sandler and Barrymore’s chemistry is unmatched, as they share many screens together. Despite Henry being once a womanizer, he realizes that some people are worth giving up that lifestyle.

I’m giving this movie a 4.9 because this movie definitely deserves the title of rom-com as it’s classic soundtrack, cast, and love story more than make up for the at-times stupid sense of humor of Adam Sandler

2. Notting Hill (1999)

One of my all- time favorites, William Thacker (Hugh Grant) owns a travel bookstore in, you guessed it, Notting Hill, when one day, American movie star Anna Scott (Julia Roberts) comes in to look at his collection, and buys a few books. They meet again when William spills orange juice on her the same day, which leads to a passionate kiss, and an eventual affair, and after a failed marriage, and many failed first dates, he brings Anna around to his friends, who happen to mesh very well with her. Their different lifestyles separate them, but fate brings them together again when she turns to him when a scandal appears involving her in the media.

Hugh Grant’s awkwardness is a perfect match for Julia Robert’s gracefulness on the screen, as she plays  a role very similar to that of her own life as she was one of the most popular actresses of the 90’s. Hugh Grant’s delivery and timing also create the perfect combination of charm and quirkiness, and as we watch Julia Roberts fall in love on- screen, the audience can’t help but fall in love with them, and Hugh Grant as well.

If it were up to me, I would definitely dub this movie one of the best romantic comedies that has been made because it’s loved by all (women), and men even admit to enjoy it as well. I’m giving this movie a 5/5 because it doesn’t automatically give the audience the satisfaction of knowing that they will end up together because let’s face it, a mundane British guy ending up with one of the most revered movie stars of her era? Impossible. But it is, and the audience, along with William, has to wait to find that out till the end when Anna Scott says she is staying in London “indefinitely”

1. When Harry Met Sally (1989)

Here it is, folks. If you stuck around, congratulations. If you just scrolled to the bottom to see what was the best rom-com to ever exist, also congratulations. Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) meet just after college when they drive from Chicago to New York together, during which they argue about if men and women can be platonic friends. Ten years later and they meet in a book store in Manhattan, and become closer friends, while also attempting to set up their best friends with each other. Over time, they date different people while remaining close friends, but what they both don’t know about  each other is that they are both in love with one another.

If you like slow-burn (when nothing happens with the two characters until the end), this movie is for you. Throughout the movie, the banter between the two main characters is natural, and definitely platonic up until the moment they are intimate. The pair not only has chemistry romantically, but also make a great friendship duo as they have a lot in common, but they argue constantly, which is both entertaining and hilarious. I think the aspect of this movie that everyone loves is that it is not a typical love story at all, in fact, it is more about friendship and the natural occurrences of life, as they both go through marriages, girlfriends and boyfriends, and watching other people get married and remain married, which is how life works.

Yes, some of the lines are cliché, but I still rate this movie a 5/5 because of how natural of a love story feels. With some movies, the love story feels rushed, and this is the total opposite because most of the time, love comes naturally in time, love doesn’t come immediately, and this is why it is number 1 on my list.