In my opinion, nothing truly encapsulates the essence of Valentine’s Day like a good rom-com. Whether you are watching it with a significant other or a group of friends, there is always an aspect of relatability and light-heartedness that enables one to enjoy this genre with any audience. They are funny, romantic, and sometimes not realistic whatsoever, which allows one to be immersed in the movie’s “fantasy” of love and humor. Rom-coms are comfortable, you know they will never have a bad ending, a scare, or a scream—the ultimate comfort movies. Take this list as a gift to you—my version of a Valentine’s Day rose or chocolate in the shape of a 10-movie list filled with a diverse flavor of rom-coms. Do not take the order too seriously except for the top three—they are the best and my opinion will not be swayed!
10. The Proposal
In The Proposal Sandra Bullock plays a successful business woman, Margaret, who desperately needs a visa to keep her job, or she will be deported back to Canada. In order to delay her deportation Ryan Reynolds, playing her assistant, Andrew, is persuaded by Maragaret to pretend to be her fiancé. The parameters of this agreement are simple: Andrew will pretend to be her fiancé as long as Maragret visits his eccentric family with him in Alaska. Margaret’s tough exterior contrasts with Andrew’s openness and ease, allowing her to open up, which creates a funny and unexpected pairing.
9. Crazy Stupid Love
Crazy Stupid Love compiles three different love stories and ends in a shocking scene that connects them all. The ending is unexpected and funny, leaving the viewers on their toes. On top of that, Ryan Gosling and Emma Stone play one of the central love stories in the movie. They are one of my favorite Hollywood pairings (see them together in La La Land), so I enjoyed seeing their chemistry, yet again, on screen.
8. 13 Going On 30
13 Going On 30 stars Jennifer Garner, who plays Jenna Rink, an unpopular 13-year-old who wishes to be an adult with a perfect life and boyfriend. Once her wish comes true, she realizes that being an adult is not not like the fantasy that she created in head.
7. Notting Hill
I recently watched Notting Hill and was shocked I hadn’t seen it before. Julia Roberts plays an American movie star who falls in love with a man who owns a bookstore in the Notting Hill neighborhood of London, played by Hugh Grant. This movie is funny and heartfelt as it follows their on and off relationship.
6. How To Lose a Guy In 10 Days
Advice columnist, Andie, played by Kate Hudson, is writing a story on how to lose a guy in 10 days, so she sets off to test her theories for the sake of the story. She meets Ben, played by Mathew McConaughey, who is convinced he can make any woman fall in love with him in 10 days. Both plans backfire. Ha ha!
5. 10 Things I Hate About You
A classic that you must watch. Julia Stiles plays an abrasive high schooler, Kat, who is quite the opposite to her popular and well-liked sister, Bianca. Kat and Bianca live in a strict household, abiding by the rule that they both cannot start dating until the other has a boyfriend, too. This does not bode well for Kat’s sister who dreadfully wants to start dating, yet Kat has no interest. In return Bianca creates a plan to set up Kat with Patrick, who is played by Heath Ledger. A modern take on Taming of the Shrew, the movie follows the guarded and ambivalent Kat as she finally lets her guard down and allows someone to love her for who she is.
4. 50 First Dates
Adam Sandler and Drew Barrymore play Henry and Lucy in 50 First Dates. Henry meets Lucy at a diner and is immediately head over heels for her. When he returns the next day, he realizes she remembers none of their interaction from the day before. He inquires about this strange phenomenon and is told she has short-term memory loss. The movie follows Henry’s journey in pursuing Lucy through these complicated circumstances, with the hope that he can make her fall in love with him day after day.
3. The Holiday
Although this is very much a Christmas movie, it is perfect to watch over Valentine’s Day, as well. Cameron Diaz and Kate Winslet play women who are utterly sick of their everyday lives and need an escape from reality. As a result, they decide to swap houses over Christmas, hoping for an escape from heartbreak, but both unexpectedly end up finding their person.
2. He’s Just Not That Into You
This movie follows three different couples through their complicated journey of finding “the one.” The plot that intertwines these three stories is compelling and unlike any other rom-com. The underlying message of “he’s just not that into you” is a harsh reality to face, but trust me, the ending is worth it and catches you by surprise. Additionally, what continues to draw me to this movie is the reliability of the characters as they navigate their complicated love lives.
1. When Harry Met Sally
This is my all-time favorite rom-com. It is a classic. It is not cliché. It is a must watch! This story takes the title characters from enemies to friends to lovers back to enemies and finally the ending leaves your heart full and in awe. The movie spans across the many years of Harry and Sally’s relationship and explores how an unlikely pairing can become something more. Leinders? Flovers? Just watch it.
Honorable mentions: Crazy rich asians, Just Go With It, Anyone But You, Friends With Benefits, Mamma Mia, Meet The Parents
