Whether you are in the mood for love, looking for something to help you believe in love again or just looking for something to help you forget that painful heartbreak, There’s a movie for everyone in every situation on Valentine’s Day. Here are 25 movie suggestions for the day of love as selected by our staff.
THE HALL OF FAME
THE BEFORE TRILOGY (RICHARD LINKLATER 1995-2013)
More so than any other entry, Richard Linklater’s The Before Trilogy is probably the most comprehensive depiction of love in all of its forms, and how it changes over time. We first meet Jesse (Ethan Hawke) and Celine (Julie Delpy) in Before Sunrise as two young, carefree spirits who happen to meet on a train ride across Europe. Through their lengthy discussions about everything from life, politics, their own personal ambitions, and desires, the very beginnings of their love begin to blossom, creating one of the purest, most innocent, and hopeful views of young unconditional love. After their first brief encounter, they do not see each other again until nine years later in Before Sunset. Time has changed them in ways that they would never have thought nine years ago, and life had plans for them that make their desires for one another more complicated and nearly impossible to achieve.
Once we get to the final film in the trilogy Before Midnight, those two hopelessly naive lovers from the first two films have all but completely disappeared. The spark that lit their romance is almost out, and their bitter resentment towards each other only grows as they continue to remain unhappy together. A large portion of this film is a nearly 40-minute long argument where every single painful memory is recalled and all of their frustrations and dissatisfactions are brought to the forefront. It’s heartbreaking to watch this once hopeful, lovestruck couple basically ready to call it quits after over ten years together. Through all of the pain and unhappiness, they ultimately reconcile their love and work to better the life that they have chosen to share together. The Before Trilogy is one of the most honest and realistic depictions of a relationship through all of its wonder as well as its hardships. – Mike Pisacano
WHEN HARRY MET SALLY (ROB REINER, 1989)
The rom com as we know it today owes a lot to two films: Woody Allen’s Annie Hall and Rob Reiner’s 1989 classic When Harry Met Sally. But where Annie Hall is like the Bill Russell of rom coms pioneering the genre and demonstrating excellence that is revered to this day, When Harry Met Sally is like the Michael Jordan of romcoms, revolutionizing the genre making it marketable to the masses effectively paving the way for the influx of rom coms throughout the 90s.
Penned by the late great Nora Ephron who would go on to make some of the marquee rom coms of the 90s (Sleepless in Seattle, You Got Mail). When Harry Met Sally is the story of well…when Harry (Billy Crystal) met Sally (rom com queen Meg Ryan). Becoming a cultural touchstone behind scenes such as “I’ll have what she’s having” and bringing many rom com staples into the popular vernacular (such as the thin line between friendship and romance) When Harry Met Sally’s influence is monumental. – Nate Lam
THE HOLIDAY (NANCY MEYERS, 2006)
Next to Ephron on the “Rushmore of Rom Coms” is Nancy Meyers hence the reason The Holiday is on this list. Starring Kate Winslet and Cameron Diaz (themselves monumental figures in the romance genre) as two women who looking for an escape from their normal lives agree to an international house swap. Once there, both find themselves caught in romantic entanglements with Jack Black and Jude Law respectively.
The rest plays out in typical rom-com fashion but what separates The Holiday from the plethora of similar movies is Meyers own unique spin on the genre (including her unparalleled flair for interior design – a trait seemingly passed on to her daughter) and the overall strength of the four core performances. Winslet, as you might expect, elevates the film to a different level which paired with Black’s every man goofiness allows for an interesting dynamic. Diaz and Law are also solid with Law in particular seemingly squandering his Hugh Grant potential in his career choices following The Holiday.
If you are in search of a conventional rom-com today. Look no further than The Holiday for there are few out there making these movies that have the style that Nancy Meyers does but I suppose that’s why she is considered one of the best. – Nate Lam
FOUR WEDDINGS AND A FUNERAL (MIKE NEWELL, 1994)
Rounding out the rom-com trinity is Richard Curtis who’s credits include Love Actually, About Time and Notting Hill. But the film that we have chosen for this list is one of his earlier credits in Four Weddings and a Funeral. Curtis did not direct this particular feature but he did write the screenplay for what would be one of many collaborations with Hugh Grant.
Here the British star plays Charles, a mild-mannered every man who develops feelings for an American (Andie McDowell) over the course of various meetings at the titular Four Weddings and a Funeral. Playing to British sensibilities, what follows is a will they – won’t they push and pull with various hijinks in between facilitated in part by Curtis regular Rowan Atkinson who provides comic relief throughout. Grant would establish himself as much more of a suave object of desire in films such as Bridget Jones’ Diary and Curtis would helm other more well-known works in the genre as the years passed but this early team-up between rom-com superstars would set the blueprint for what was to come. – Nate Lam
HAPPY TOGETHER (WONG KAR-WAI, 1997)
If you’re alone this Valentine’s day, you may want a reminder that love can be hard and painful. Happy Together follows an abusive Hong Kong couple who travel to Argentina in the hopes of making a fresh start. But the pair is no good for each other, and rarely seem to get along. Having separated, they find themselves without enough money to get home and must live alone in the city while occasionally colliding with each other in violent and heartbreaking fashion, falling in and out of love. With an ironic title, this is certainly not one to watch on a romantic date, but Kar-Wai presents a brutal… and ultimately hopeful illustration of toxic romance and unconditional friendship. – Ethan Kruger
IL POSTINO (MICHAEL RADFORD, 1994)
This film is a true testament to the power of love and literature. It’s not only a feel-good movie but a simultaneously deeply intelligent film. Love doesn’t just transform us but so can the written word; in fact, the transformative effect love and poetry have on our characters (and the audience as well) is beautifully developed and emotionally rewarding.
Il Postino really is a nice little movie, with beautiful vistas, music, and characters. A definite must-see for moviegoers of any stripe and a cherished part of Italian cinema. – Michael Vecchio
BLUE IS THE WARMEST COLOR (ABDELLATIF KECHICHE, 2013)
Abdellatif Kechiche’s Blue is the Warmest Color is a romantic drama centered around two girls and their torrid relationship of lust, love, and heartbreak. Young love is almost always doomed because of the relative inexperience of the parties involved. Managing the complexities of powerful emotions is difficult enough but this is further exacerbated by societal expectations. Kechiche plays with these elements in a film that is much more than meets the eye. It is simultaneously a coming of age tale with hints of commentary on social class, economic strife and the exhilarating highs (and depressing lows) of love and heartbreak. – Nate Lam
ALI: FEAR EATS THE SOUL (RAINER WERNER FASSBINDER, 1974)
Love blossoms against all odds in Ali: Fear Eats the Soul as a 60-year-old cleaning woman falls for a much younger Moroccan migrant worker in post-war Germany despite the rife racism pervading her community. The couple receives a barrage of abuse and mistreatment from neighbors, colleagues, and complete strangers, due not only to miscegenation but also in regard to the age difference between the pair. Refusing to bow down to the pressures around them, their love remains mostly steady until the bitter end, and Fassbinder’s outlook on unstoppable love is reaffirming and optimistic. – Ethan Kruger
IN THE MOOD FOR LOVE (WONG KAR-WAI, 2000)
Arguably Wong Kar-Wai’s greatest work, In The Mood For Love joins Happy Together as another film in the Kar-Wai ouevre that tackles themes of isolation, longing and the pain of unrealized love. Once again enlisting the talents of Tony Leung in the lead role, he engages in an emotional affair with the woman next door (Maggie Cheung). Both unsatisfied by their respective marriages and suspecting that their spouses are unfaithful, the pair’s romance is one that exhibits itself almost entirely in stolen glances, brushed shoulders and innocent dialogue (with a flirtatious subtext).
Kar-Wai shoots the film beautifully (with the help of cinematographer Chris Doyle) capturing 60s Hong Kong with delicate use of lighting and color. The secretive nature of the film and the powerful score help accent a film that masters subtlety. This is a film that you can return to time and time again and find something new to appreciate because Kar-Wai so wonderfully navigates the nuances of the affair at hand. By the time the credits roll , you are left wondering why you feel so deeply for a relationship that existed so covertly. One that demonstrates as much passion in a glance as the most fiery of romances and one that chooses not to loudly proclaim its desire to the world in a grand romantic gesture but rather as a whisper. – Nate Lam
LOST IN TRANSLATION (SOFIA COPPOLA, 2003)
Sofia Coppola’s masterpiece Lost in Translation is an examination of isolation, existential ennui and the power of human connection. Bill Murray plays Bob Harris, an aging actor long past his marketable prime while Scarlett Johansson plays Charlotte a new graduate looking to find her direction in life. Through the mysterious powers of serendipity, they find their way to one another bonding through mutual feelings of alienation in the foreign land of Tokyo Japan.
Coppola lets the film come into its own building the city of Tokyo into its own character both foreboding and foreign yet also a place capable of providing enlightenment and adventure. By forcing her characters out of their comfort zones she allows them to confront their own inner turmoils. Charlotte is blessed by the endless opportunities for her life ahead but is trapped in a neglected marriage and the lack of direction when it comes to the many paths available to her. Bob, on the other end of the age spectrum, is faced with the question of whether the choices he did make were the right ones or if his lavish status as a celebrity is an illusion of happiness.
It is a fascinating character study that also functions as a beautiful love story. Though it is not played out in the traditional sense of passion and sweeping declarations, it is a muted reflection on the importance of human connection – of having someone who can relate and help you through those moments when you are lost and in need of someone to tell you “It gets easier”. – Nate Lam
WALL-E (ANDREW STANTON, 2008)
While Pixar’s 2008 Academy award winner is more often recognized as a grand science-fiction narrative, in its tale of environmentalism and futuristic social commentary, what cannot be stated enough is that it also delivers as one of the very best love stories among any of the studio’s projects. Often time in film, the most effective love stories told are the romance that forms from the most unlikeliest of sources. But where one really shines, however, is just how unlikely this source really is and is no better represented than in the one inspiringly shared between 2 robots. An achievement that, when considering on how much limited dialogue is verbally shared between WALL-E and EVE, relying heavily on the use of interaction and expression that until then could only be traced back to the SIlent Era, was no simple task for Stanton and his team. But through the incredible animation and writing that by today is expected no less than the very best from the studio, it was a challenge they were more than willing to face and the resulting masterpiece clearly speaks for itself. – Ken Sims
PHANTOM THREAD (PAUL THOMAS ANDERSON, 2017)
Anything but the conventional rom-com, Phantom Thread is the one to watch this Valentine’s Day if you’re looking for a trip to the cinema. Spellbindingly complex in its depiction of the male genius and his muse, Phantom Thread presents themes of toxic masculinity and psychologically abusive relationships without allowing the girl to become a victim, instead, using deviant methods in order to lull her male counterpart into submission. All Alma (Vicky Krieps) wants is for her partner, dressmaker Reynolds Woodcock, to be in some way dependent of her, while Woodcock requires someone to rescue him from his work-obsessed and destructive nature, and through twisted means, the couple may just find what they both need. – Ethan Kruger
ETERNAL SUNSHINE OF THE SPOTLESS MIND (MICHEL GONDRY, 2004)
Michel Gondry and Charlie Kaufman’s cerebral journey through the mind asks the question, “If you could erase someone from your memory, would you?” After a bad breakup, Joel (Jim Carrey) and Clementine (Kate Winslet) undergo a medical procedure to erase all memories of their relationships and of each other out of their minds. While it sounds like a good idea at first, Joel quickly realizes the mistake that he’s making in allowing these memories to be removed. Confronting such immense heartbreak can be hard, and it almost might seem easier to just get rid of all of those painful memories so you don’t have to deal with them anymore, but it’s those experiences that shape who we are and allow us to mentally and emotionally mature over time. Presented with some of the most inventive editing and camera techniques seamlessly blending memories together, Eternal Sunshine of the Spotless Mind is a psychological window into some of our most challenging emotional hardships. – Mike Pisacano
THE SHAPE OF WATER (GUILLERMO DEL TORO, 2017)
In a career of over two decades, Guillermo Del Toro has proven himself time again as practically a gift to cinema, particularly in his ability to successfully deliver original and creative projects spanning and coinciding across various genres. With the premise of his latest feature, Del Toro draws upon a childhood question as intriguing as much as it is bizarre: “What if in The Creature from the Black Lagoon, the Gill-Man and Julia Adams succeeded with their romance?”
What follows is a striking fairy tale set of misfits from very different walks of life set within the turbulent times of 1960s Cold War America, and all the good and bad that comes with it. And at its very heart, comes honestly one of the surprisingly best love stories of last year; delivered to great effect and chemistry between Sally Hawkins and underrated creature performer Doug Jones. – Ken Sims
(500) DAYS OF SUMMER (MARC WEBB, 2009)
The poster child for “cute, quirky, indie romantic comedy”, yet what often gets overlooked about (500) Days of Summer is that it actually critiques many of the tropes and cliches that have been created within this genre and their influences on the way we perceive relationships in real life. It’s so easy to completely villainize your ex after a relationship ends and paint them as cruel, heartless monsters for daring to break up with you. It would have been just as easy for (500) Days of Summer to only sympathize with Tom’s (Joseph Gordon-Levitt) perspective in this breakup, but it also makes us consider Summer’s (Zooey Deschanel) position as being just as, if not more, valid.
Breakups are a natural part of dating, and they’re not usually meant to be malicious dismissals of your significant other. Forcing things to work out even if they’re not, is arguably more harmful to the relationship and to your own well-being. For most of the runtime, we are expected to believe Tom, that everything was going great until Summer just unexpectedly broke up with him for no reason, that is until Tom, as well as the audience, is asked to reevaluate the events from her perspective, and to be willing to accept some of the blame for things turning sour. Being broken up with can be an emotional gut punch, but those experiences are what allow us to pick ourselves up, get back out there, and try again, because love is irrational, but it’s what keeps us going. – Mike Pisacano
CITY LIGHTS (CHARLIE CHAPLIN, 1931)
It doesn’t get more classic than Charlie Chaplin and City Lights. Telling the tale of a tramp (played by Chaplin himself) and his attempts to help a blind woman (whom he falls in love with) see again, City Lights is a heartfelt tale on the lengths we go to for love. Directed and produced by Chaplin in everything from the acting to the self composed score and sound design, City Lights remains an iconic film worthy of a watch almost 90 years after its release because the passion that Chaplin showed for the project shines through to this day. – Nate Lam
CASABLANCA (MICHAEL CURTIZ, 1942)
Like a fine wine, Casablanca is the type of film that only gets better with age. And while it has a definite time period, its timeless themes of love, friendship and patriotism have made Casablanca essential viewing for over seven decades. Winner of three Academy Awards, this tale of lost and reclaimed love in the middle of war has remained forever relevant precisely because it chronicles the beauty that is human love. No matter how far we progress (or regress) technologically, basic human emotions will never change. Thus despite its setting, Casablanca can be transferred anywhere and anytime. This ageless quality is one of the reasons it remains one of the few black and white films that even the general public will know of, off the top of their head.
While Rick and Ilsa will always have Paris, we are fortunate enough that as time goes by we’ll always have this treasure of a film. – Michael Vecchio
MARTY (DELBERT MANN, 1955)
Penned by renowned writer, Paddy Chayefsky, Marty is a charming, simple and romantic portrait of 2 regular ordinary souls, led brilliantly by the late-but-great character actor Ernest Borgnine, just looking for love in a world where to him it seems entirely non-existent. Sometimes when it comes to love, it seems all too easy for one to feel somewhat discouraged in life when regarding prospects of a meaningful relationship. You believe it could happen, but more often than not it can sometimes feel it’s more likely reserved for others than yourself. And in living with such things, it can certainly be hard. But then there comes a refreshing little movie that can show that love and happiness never announces itself as your typical romance story may have you think, and that such things are not always out of reach. With some of Chayefsky’s very best dialogue delivered with the true sincerity of Borgnine’s down-to-earth performance, as well as a strong supportive cast and Delbert Mann sensitive direction, Marty delivers an excellent true to form slice-of-life story and one of the more unique romantic dramas of its kind. – Ken Sims
BONNIE AND CLYDE (ARTHUR PENN, 1967)
Now the reference point for rebellious young love in popular culture, Bonnie and Clyde shocked audiences in the 60’s for its portrayal of brutal violence and untamed youth, particularly in its unflinching, heartbreaking, foreseeable climax. At the film’s core is a complex relationship between a man and a woman who feel constricted by social norms and values, and take to the road for a short, fast life. While the couple has their own issues and often irritate each other, Clyde requires a partner-in-crime, while Bonnie needs someone to take her away from her dull life. The pair were clearly made for each other and are both similar people, and while they are both morally questionable criminals, it is difficult not to root for the couple’s happiness even when it never seems to be on the cards. – Ethan Kruger
ARTHUR (STEVE GORDON, 1981)
Featuring a Golden Globe-winning lead from the great Dudley Moore and a highly memorable theme song, Arthur (which also won the Golden Globe for Best Musical/Comedy) is a sweet and charming comedy that highlights just how special the feeling of love truly is. For alcoholic millionaire playboy Arthur Bach (Moore), life has always been about shirking responsibilities. Kept in line by his acerbic servant Hobson (John Gielgud, in the role that won him an Academy Award) Arthur begins to mature as a person when he falls in love with the working class Linda (Liza Minnelli). But there’s one problem: the eternal bachelor must marry a wealthy socialite to keep his fortune. Will he follow his heart or will the allure of the wealthy life lead him astray?
Nominated for four Oscars and winner of two (Best Original Song, Best Supporting Actor), this funny, heartwarming and splendid film works very well as both a comedy and a romance film. In the role of Arthur Bach, Dudley Moore is truly exceptional reminding us of his immense talents, while writer/director Steve Gordon (who died the year after the film was released) showcased an auspicious career for himself before his tragic passing. – Michael Vecchio
BREAKFAST AT TIFFANY’S (BLAKE EDWARDS, 1961)
Audrey Hepburn’s most iconic role is playing Holly Golightly in Breakfast at Tiffany’s. Based on the Truman Capote novella of the same name, Hepburn’s Golightly plays the naive yet likeable socialite role living off the generosity of her male admirers. It’s a toned down version of Capote’s novel but one that viewers can undoubtedly get behind despite it’s relatively simple premise.
Thanks to Hepburn’s strong performance (highlighted by a rousing rendition of Moon River) and her chemistry with her male co star George Peppard, the charm of Breakfast At Tiffany’s is undeniable. – Nate Lam
LA LA LAND (DAMIEN CHAZELLE, 2016)
Reminiscent of classic 1950’s musicals, La La Land captures all of the charm, whimsy, and magic of a lavish Hollywood romance, but with a modern sense of harsh reality. Sebastian (Ryan Gosling) and Mia (Emma Stone) are the quintessential Hollywood couple, each with their own artistic ambitions. If this were maybe a different film, these two would be able to achieve their goals and stay with each other. Unlike most classic Hollywood romances, however, Seb and Mia don’t get to live happily ever after together.
La La Land treats both partners as individuals, with their own hopes and dreams, which sadly are not able to include each other. Through all of their personal struggles, they manage to work their way towards achieving all of their artistic goals, but at the expense of being with each other. The film ends with a bittersweet montage of what life could have been like had they been able to have both, and it serves as a much-needed reminder that life and love are not always able to be how they are in the movies. – Mike Pisacano
ONCE (John Carney, 2007)
Probably one of the most unconventional romances put to film because it really isn’t one. The film has the look and feel of a typical romance movie, yet there is no relationship to be had in Once. Never once do they have sex, never do they say “I love you”, they never even kiss. They aren’t even given names, we just know them as Guy and Girl. Once is a completely platonic relationship between two individuals who will never be able to be together. Guy and Girl are collaborating musicians whose mutual affection can only be expressed through the music that they make with each other, and the beautiful soundtrack that they compose together expresses their love more strongly than any words ever could. –Mike Pisacano
The UMBRELLAS OF CHERBOURG (JACQUES DEMY, 1964)
Cited by Damien Chazelle as the film that inspired La La Land, this Palme d’Or-winning musical was a breakout role for French star Catherine Deneuve. Initially a little jarring and difficult to appreciate but endearing and captivating after a short while, the entire film is sung with continuous music telling the story of two young lovers separated by conscription during the Algerian War. Despite the constant music, composer Michel Legrand still manages to create recognizable and memorable melodies throughout, while the vibrant colors and stylish costume designs are as vivid as ever following a restoration in 2004, led by Demy’s wife Agnes Varda. – Ethan Kruger
SINGIN’ IN THE RAIN (GENE KELLY / STANLEY DONEN, 1952)
I don’t know if there is a scene in a movie more representative of the euphoric high of being in love than Gene Kelly’s Don Lockwood singing and dancing in the pouring rain in 1952’s Singin’ In The Rain. Another major influence on La La Land, Singin’ In The Rain is considered a classic movie musical for its many noteworthy numbers including Good Morning and the titular song. Starring an ensemble cast of Kelly, Donald O’Connor and a young Debbie Reynolds the infectious energy that the cast exudes is contagious. If you are having a down day turn on Singin’ In The Rain – it’s pure positivity is an example of the magic of cinema and its power to impact people long after its theatrical run – Nate Lam