15 Best Movies To Watch On Valentine’s Day If You’re Single

15 Best Movies To Watch On Valentine's Day If You're Single

With only days until Valentine’s Day, couples must have already hatched elaborate plans to woo their partners. Reservations made, gifts bought, or plans include a simple quiet night; with a bowl of ice cream, two spoons, and a feel-good comedy ready to watch. However, all the singles out there might find such preparation infantile, irritating, or excruciatingly nostalgic. While being in love is a brilliant feeling, sometimes being independent and cognizant of the right kind of love is just as important.

RELATED: 10 Best Teen Love K-Dramas To Watch This Valentine’s Day

While couples have myriad viewing options ranging from archaic gothic romances to offbeat indie, there is no reason that singles should feel left out. Single people would rather like to see a movie that does not romanticize love but shows it through the lens of reality. It does not require the perfect ending or the need to pressure viewers into yearning for love. Perfect Valentine’s Day movies for singles should showcase the complex nature of relationships, celebrate the independence of being alone, and convey a mature understanding of love, which does not always end in togetherness.


Updated on February 10th, 2022 by Danielle Bruncati: Love is in the air once again and after spending another year in a pandemic, many singles are at their with ends with dating and being single. While it can be hard to watch love being all around, sometimes the perfect therapy is to indulge in romantic movies that feature love stories that don’t always end in traditional happily ever afters. Thankfully, there’s been a rise of these types of movies in recent years that remind people that what matters most is that they love and respect themselves first. 

Legally Blonde (2001)

Available On Hulu

Legally Blonde is one of Reese Witherspoon’s most memorable roles of all time. In the movie, she plays Elle Woods, an optimistic woman who has her world turned upside down when her long-term boyfriend breaks up with her instead of proposing. Devastated, Elle decides to win him back by following him to Harvard Law.

While that might not seem like a feminist tale, it is because in following him to Harvard, Elle proves everyone wrong who doubted her. The movie is a strong reminder to singles, especially women, that people can do anything they want to do regardless of their relationship status or hair color.

He’s Just Not That Into You (2009)

Available On Tubi

Based on a 2004 self-help book of the same name, He’s Just Not That Into You is one of the best anthology rom-coms of all time. It stars an a-list cast that includes Jennifer Aniston, Drew Barrymore, Justin Long, Ginnifer Goodwin, and Ben Affleck just to name a few.

Singles can relate to at least one of the three plots in this movie. The first follows Gigi as she enlists the help of a bartender to help her on her dates. Meanwhile, Janie is dealing with a marriage that is falling apart while Anna is determined to find true love. The movie chronicles the highs and lows of dating in the 2000s which surprisingly hasn’t changed much. It’s a perfect movie for singles to watch and commiserate together on.

Marriage Story (2019)

Available On Netflix

A still from Marriage Story showing the Barber family

Singles who have just suffered a bad divorce should steer clear of this hauntingly realistic depiction of a failing marriage. However, for those who have broken up with someone, whom they had hoped to marry, this movie would prove to be a friendly reminder that maybe it was for the better. No relationship thrives on compromises and if there have been differences that led to a breakup, being married might have made it irreconcilable.

Directed by Noah Baumbach, Marriage Story features Scarlett Johansson, Adam Driver and, Laura Dern. It showcases the journey of Charlie and Nicole Barber, exploring love, marriage, and the excruciatingly grueling experience of a bad divorce.

500 Days Of Summer (2009)

Available On Hulu

Summer and Tom Hansen talk in the elevator

The concept of soulmates, or finding “The One” might seem like a romantic utopia, but reality does not usually work in such a divine fashion. While many do find the love of their lives in their partner, others have to navigate through the treacherous trenches of failed relationships to find “The One.” But what if “The One” gets away?

500 Days of Summer, starring Joseph Gordon-Levitt, and Zooey Deschanel, is a story that intelligently talks about a painful breakup with the perfect partner and about the true realities of relationships and life. Marc Webb’s directorial debut showcases how true love is often a construct that people project in accordance with their own desires, and how life always goes on stopping for nobody. Some things are unfortunately short, but fortunately, they are sweet while they lasted. Amongst the innumerable cute teen rom-coms for younger viewers, 500 Days of Summer is a stark reality check.

How To Be Single (2016)

Available On HBO Max

The girl of How To Be Single

Liz Tuccillo of Sex and the City fame wrote the delightful novel How to Be Single and Christian Drifter adapted the same into an enjoyable movie depicting the lives of young adults in their early twenties, navigating the intricacies of the single life in the fast-moving city of New York.

Starring Marc Silverstein, Diana Fox, and Abby Kohn, How to Be Single is refreshing, cathartic, and astoundingly real. It highlights that at the end of the day, the only person anybody truly needs is themselves.

Revolutionary Road (2008)

Available On Roku Channel

The Wheelers in Revolutionary Road

There are many horror movies that are perfect for Valentine’s Day, but Revolutionary Road is haunting for a whole different reason. This movie talks about societal pressures of keeping up appearances, the monotonous and rigorous task of maintaining a marriage, infidelity, and the existence of that fanciful escape, which always seems elusive.

RELATED: 10 Best Netflix Original Rom-Coms To Stream On Valentine’s Day

Through the story of the Wheelers, acted beautifully by Kate Winslet and Leonardo DiCaprio, Revolutionary Road shrieks out the importance of stopping once in a while and putting in the effort necessary to take care of what is loved. Things that are taken for granted usually crumble, and marriage is no different. For all the singles out there, this is a reassuring movie that hauntingly portrays the reality that not all relationships are perfect, and appearances can be deceptive.

Someone Great (2019)

Available On Netflix

Cast o Someone Great sitting outside on the sidewalk

Released in 2019, Someone Great is the perfect movie for singles to watch on Valentine’s Day. The movie centers on Jenny, a music journalist in New York City who lands her dream job across the country. Unfortunately, this career-high is overshadowed when her boyfriend of 9 years breaks up with her because he doesn’t want to move.

With her two best friends by her side, Jenny decides to go on one last hurrah around the city that she’s called home for nearly a decade. The movie celebrated female friendship and also the silver lining breaks ups can bring.

Cast Away (2000)

Available On Hulu

Tom Hanks in Cast Away

Any movie starring Tom Hanks usually turns out to be brilliant, and Cast Away is no different. One of the top 10 Tom Hanks movies, Cast Away tells the story of a disciplined FedEx employee Chuck Noland hurled into the uncertain realities of having to face the extremities of being stranded on an uninhabited island while holding on to the undying hope of returning to the person he loves.

Noland survives his ordeal, returning only to find out that he has lost his beloved all over again and must learn to live in a world that seems to have moved on. This movie shows how powerful hope can be, while also depicting that hope is usually not enough in the real life.

Mama Mia! Here We Go Again (2019)

Available On Hulu

Original cast of Mamma Mia! Here We Go Again (2018)

While the original Mamma Mia is also about love and weddings, Mamma Mia! Here We Go Again is all about the fun that a young woman can have when she’s single in a foreign country. The movie follows young Donna on her escapades that led to her getting pregnant with Sophie.

Watching Donna have fun in Greece with her best friends is everything. She’s unapologetic and having fun which is the exact thing all the singles should be doing on Valentine’s Day.

Under The Tuscan Sun (2003)

Available On Roku Channel

Diane Lane as Frances Mayer in Under The Tuscan Sun

In the movie Under the Tuscan Sun, Frances Mayes (Diane Lane), a writer discovers that her perfect life is a terrible façade with her husband cheating on her with his lover whom he has gotten pregnant. As Frances starts losing herself to depression post-divorce, she pays heed to the suggestion of a friend and goes on a vacation to Tuscany to distract herself. What she ends up achieving is rediscovering her life, confidence, and happiness while being completely on her own.

This 2003 movie is the perfect flick to watch for someone who feels like the world has ended after their last breakup. It reiterates that being alone does not necessarily mean being unhappy and that happiness can be found if an effort is made to achieve it.

The First Wives Club (1996)

Available On Hulu

Diane Keaton, Bette Midler, and Goldie Hawn in The First Wives Club

This empowering and funny movie starring the terrific trio of Diane Keaton, Bette Midler, and Goldie Hawn tells the story of three middle-aged divorcee college friends reuniting after 30 years during the funeral of their friend. The friend had died after being ditched by her ex-husband for a younger woman and upon learning the reason, the three friends realize that even their ex-husbands have taken them for granted in the past; an indiscretion deserving of revenge.

The First Wives Club is the perfect and funny detour to take from the sappy romantic comedies that plague Valentine’s Day.

A Streetcar Named Desire (1951)

Available On HBO Max

Vivian Leigh and Marlon Brando as Blanche DuBois and Stanley Kowalski in A Streetcar Named Desire

Although there are myriad recently released movies and shows that complement Valentine’s Day, singles might just prefer to settle for the old and classic in the movie adaptation of Tennessee Williams’ Pulitzer Prize-winning masterpiece A Streetcar Named Desire.

RELATED: Marlon Brando’s 10 Best Films, According to IMDb

Starring the iconic Marlon Brando as Stanley Kowalski, and Vivian Leigh as Blanche DuBois, this movie bolsters that relationships are usually not how they are romanticized to be. The haunting lines, “I have always depended on the kindness of strangers” ironically reiterates the vulnerability of love and how the lack of independence has ruined Blanche’s life.

Bridesmaids (2011)

Available On Peacock

Lillian and her bridesmaids visit a dress store in Bridesmaids

Kristin Wiig and Maya Rudoph both got their start on Saturday Night Live but they reached true comedy genius when they starred opposite each other in Bridesmaids. Written by Kristen Wiig and Annie Mumolo, the movie centers on Annie, a down on her luck single woman whose maid of honor duties are being stolen by one of her best friend’s other bridesmaids.

Annie’s character progression is iconic in this movie and a great reminder that sometimes it takes hitting rock bottom to find true happiness again. While there are love subplots in the movie, a large portion of it focused on friendship making it a great Valentine’s Day movie for singles.

Forgetting Sarah Marshall (2008)

Available On Amazon Prime Video

The ensemble cast of Forgetting Sarah Marshall

Another movie discovering the simple yet extremely difficult task of moving on from love, Forgetting Sarah Marshall gleefully depicts Peter Bretter’s attempts of forgetting his famous and seemingly perfect ex by going on a vacation to Hawaii.

The screenplay of this movie written by Jason Segel, who also stars as Peter, sees it hilariously portraying the dreaded and painful idea of meeting up with an ex and their current partner, as well as reminding viewers that a breakup usually does not mean the loss of all hope.

Gone Girl (2014)

Available On Hulu

The Dunne's in Gone Girl

Gone Girl is a movie that reiterates that it is not men or women who cause a relationship to falter, but that each is equally responsible for causing strains, and perhaps for the very reason make them interesting partners.

The lines “What have we done to each other? What will we do?” seems to echo throughout the movie, as singles can rejoice in the fact that they have not partnered with a cunning psychopath or a carnally driven cheater. Starring Rosamund Pike and Ben Affleck, this David Fincher thriller is an absolute delight and has deservedly received various nominations and awards.

NEXT: 10 Best Movies With Happily Single Protagonists To Enjoy On Valentine’s Day

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Arnab Rakshit
(79 Articles Published)

Arnab Rakshit is an avid reader, writer, movie-buff, and comics fanatic residing in Kolkata, India. He is a graduate of Asutosh College, Calcutta University, with a Bachelor of Arts degree in English Literature. Having worked in the field of content development for myriad clients since 2016, he is confident about creating meticulous and informative content for ScreenRant readers. He also enjoys a competitive game of Table Tennis once in a while.

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