The Masochist’s Guide to Valentine’s Day: A Bunch of Films to Torture Yourself With

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Eternal Sunshine Meet me in Montauk

We can assume that if you are looking at this list, you are probably single, or in a complicated relationship with your cell phone, or deeply committed to sitting in your bed watching Netflix and crying while holding a pint of ice cream in your left hand. The last thing you turned on was your coffee machine. Your credit card company called you based on five suspicious charges at Munson’s, Godiva, Ghirardelli, Pizza Hutt, and Jelly Belly. (Did I do this? Don’t be silly.) Valentine’s Day is near , and you are left listening to your friends around you talk about their various plans with their significant others, and you put on a brave face congratulating them, when you’re really hoping that they’ll jump in front of a bus or something. (Or, if you’re like me, you’re just very explicit about that last part and don’t bother with being happy for your friends. I know, I’m a horrible person.) Thusly, I took it upon myself to compile a list of great films to allow you to revel in your pain. Because there’s nothing like watching other people live out romances that you keep convincing yourself you will never experience personally. Like any good masochist’s Anna Howard Shaw Day Party, pizza and ice cream are a must as well as a Wi-Fi connection, so you can openly complain about how bitter you are on the numerous social networking accounts you have. Without further ado, here are the best films to torture yourself with on Valentine’s Day.

The tree of life Antichrist

Honorable Mention: Antichrist (2009) | Directed by Lars von Trier

I went for a much more literal interpretation of “torture” than you would expect, I guess. Lars von Trier’s hypnotic, horrific, provocative, and profoundly fascinating film depicts the dissolution of a marriage in a cabin in the woods, where gender politics becomes manifested as a violent battle. I mean, if the smashing of typical gender roles (and genitalia) is your kinda thing for Valentine’s Day, have at it. As terrifying as the film is, the Danish auteur’s ability to bring the visceral embodiment of anxiety to the screen, through images, sounds, and emotions, makes it one of the most intense films ever. HAPPY VALENTINE’S DAY TO YOU.

Should You Be Masochistic Enough to Actually Go Out in Public: Her (2013) | Directed by Spike Jonze

I’m all for staying in and not leaving my bed, except to, like, get food or more tissues. But, for those of you that have more energy and don’t mind crying around people, Spike Jonze’s near-futuristic love story is the thing to see. Her woos and captivates. It is heartwrenching for a few reasons: a) you’re watching a man (Joaquin Phoenix) who, after a recent breakup, is slipping into a relationship that is basically too good for him to be beneficial, b) you’re watching that relationship grow and evolve and become something completely authentic, c) are you crying yet? Jonze’s goal isn’t to patronize or preach about the relationship we have with technology, but to legitimize any kind of relationship.  So, if you happen to be, or have been, in a long distance relationship, this film will be really fun for you. Intangibility of love has never been so sweetly painful. And though the film is at times melancholic, Her is nonetheless an astonishingly honest film about love and maturity. And don’t lie: I know the most important relationship you have is with your phone. I know how you feel.


Something to Throw Into that Heteronormative Mix: Weekend (2010) | Directed by Andrew Haigh

All the films in the list are about straight people, which is a problem. So, I added this.  There seems to be a (fairly natural) assumption that one night stands or hookups can be relatively awkward. One is kind of commodifying what was once considered sacred, and it is supposedly devoid of any intellectual or emotional intimacy. Yes, they can be like that, but Andrew Haigh’s astonishing film Weekend goes to show that even the quickest, most transient moments of intimacy, sexual or otherwise, can still be important. While Russell (Tom Cullen) and Glen’s (Chris New) original intentions were to only be together for one night, their weekend explores the nuances and complexities of sexuality as a whole. Weekend succeeds not merely because of its specificity with regard to queer living, but because of its universality and resonant approach to love.

Threesomes Are Complicated: Heartbeats (2010) | Directed by Xavier Dolan

I have no interest in ever being in a threesome because I would end up on the side snacking. So, instead I watch Heartbeats, which is less literal and more figurative in that respect. It would be terribly reductive to describe Xavier Dolan’s sophomore effort as “hipster Jules and Jim”, but thinking it as a contemporary update of those same dynamics and politics, it’s pretty successful. Dolan’s “film school” aesthetic, for which he has come under fire occasionally, might be in full bloom here, but as opposed to distracting from the film its swoony, passionate aesthetic aids in its depiction of impossible desire. Dolan’s greatest strength as a director (the bastard) is getting at the very core of certain emotions, namely love, desire, pain, heartbreak, and friendship. Heartbeats, arguably more than his other work, cuts deepest.


10. Lost in Translation (2003) | Directed by Sofia Coppola

If you are feeling a little lost and disconnected this Valentine’s Day, why not take a moment to… fly to Tokyo with your aloof and distant significant other, realize you feel lost in the world, and then make friends with someone else, someone with whom you are able to connect to emotionally during this state. That’s what Scarlett Johansson does in Sofia Coppola’s film about ennui and the people you meet while wandering through life. The interesting thing about this on screen romance is that it’s not technically a romance. The connection that Johansson and Bill Murray have is one of comfort and trust, not one of an explicitly sexual nature. What you feel between the two isn’t so much a sexual tension, but almost a smoothness. One gets the feeling there is an understanding between the two, and that level of trust is all you need. Shame you can’t get that with that Flappy Bird app.

9. In the Mood for Love (2000) | Directed by Wong Kar-Wai

The film that inspired the previous entry, Wong Kar-Wai’s decadent look at forbidden love is one of the most intoxicating experiences in film. Christopher Doyle’s cinematography and the slow burn nature of temptation running through the film leaves you buzzed like the strongest drink imaginable. Underneath that stupefying, sensual surface is one of the deepest felt desires set to celluloid. Maggie Cheung and Tony Leung’s chemistry seers the screen, leaving a burn mark you’ll try to get out of your heart to no avail. For a romance that that ends up remaining within the realms of passionate yearning, few other romances feel so complete. (I guess you should order Chinese instead of pizza if you’re gonna watch this one, right?)


8. When Harry Met Sally… (1989) | Directed by Ron Reiner

Everyone has fallen in love with their best friend at some point, right? If you haven’t, I guess you can skip this one. Regardless, Nora Ephron’s intelligent screenplay may have started a billion knockoffs, but none of them compare to this one. Ephron shows what it is actually like to have a friend whom you are not initially attracted to connect on a deep level, where sex isn’t a necessity. Where it’s the intellectual connection that matters more. Fiascos happen and you realize that you may crave more, and that happens, and it’s heartbreaking, and the film shows us that astutely through the eyes of Harry, the Cynic (Billy Crystal) and Sally, the Neurotic (Meg Ryan). Although Rob Reiner and Ephron certainly borrowed from Woody Allen, the creation is all its own, a testament to friendship, not the romance that gets in the way, nor the unrequited feelings that some people end up thinking define that dynamic. In the original script, Ephron wanted Harry and Sally to go back to being friends and not end up together. Audiences wouldn’t have it, but to this day, they agree that that ending was more realistic, which is correct. On the plus side, as you listen to Harry spit out one of the most romantic speeches in film history, you can totally snack on that $50 worth of chocolate you shelled out on Monday.

7. Casablanca (1942) | Directed by Michael Curtiz

Would it be a cop out if I just left a quote in this section to explain it all? Probably. The one that may stand out most is, “We’ll always have Paris.” Rick’s (Humphrey Bogart) cynical shell melts off briefly as he bids his love Ilsa (Ingrid Bergman) goodbye, understanding that she is truly better off with the man who can provide for her. Rick understands that, as lovely as Paris was, that it’ll be a highlight in his romantic mind, something that can never again come to fruition. This bravery and honesty to let the one you love go and allow them to be happy is the kind of thing that will assuredly leave tear stains on your pillow for the next dozen or so decades. Everyone wants a romance like Rick and Ilsa’s, but they often forget the sacrifice involved and the heartbreak that ensues. Cue ugly crying.

annie hall

6. Annie Hall (1977) | Directed by Woody Allen

Once again, a film whose romance is too oft portrayed as being picture perfect, thus ignoring the point of the film: almost no relationship is like that. Annie Hall’s goal is to portray the nuances and hardships of a relationship, from the petty jealousy to the ridiculous expectations of change for the other person. In many ways, the relationship between Alvy Singer (Woody Allen) and Annie Hall (Diane Keaton) isn’t really a great one. Alvy is sort of demeaning, Annie is too manic. (You could hypothetically argue she becomes a Manic Pixie Dream Girl, but she’s ends up autonomous in the end.) Nonetheless, the sweet memories that make the film so iconic (“I lurve you…”) are so for a reason; they conjure up the emotions one feels when one is madly in love. It’s funny and painful because of its interesting balance of the two, and the acknowledgment that, uh, as the old joke goes, most of us need the eggs.

stranger than fiction

5. Stranger Than Fiction (2006) | Directed by Marc Forster

Stranger Than Fiction isn’t strictly a romance as it is more concerned with life itself. But, part of “life itself” is love, and Harold Crick (Will Ferrell) falls for the anarchist baker Ana Pascal (Maggie Gyllenhaal), a woman whom he is auditing for the IRS. While the film plays with the ideas of literary theory, narrative arcs, and the difference between comedy and tragedy, one of the strongest, yet most understated, qualities is how it approaches love. Crick is a man who has spent his life following a routine, one that is, in the grand scheme of things, fairly meaningless. For once, Harold allows himself to be consumed by living life, which includes falling in love. Harold loves little details in things, but he seems to take a breath and just lie on the couch with her, watching old movies, getting a grip on “the unrelenting lyrics of those numerous punk rock songs told him to do. Harold Crick lived his life.” And what a gorgeous life that is, you can think as you weep into your ice cream.

4. The Purple Rose of Cairo (1985) | Directed by Woody Allen

You know, when in doubt, fall in love with something/someone intangible. Like your operating system. Or a character in a movie. I suppose the concise, if not simple, answer to why we torture ourselves like this is that it provides a certain amount of solace. Depression Era Mia Farrow falls for Roaring Twenties era Jeff Daniels, the latter of whom is technically a goofy, warm hearted archeologist who just so happens to be a character in a movie called The Purple Rose of Cairo. But who is Farrow’s Cecilia really in love with: the film she goes to incessantly to escape the realities of her life (the abusive husband, the lack of a job) or the idealized portrait of a lover who simply jumps off the screen to be with her? The film is as heartbreaking as it is charming (damn is it charming), and while it is a profound love letter to film itself, it is as much a warning to those who get too caught up in the magic, not realizing that soon reality with rear its ugly face again. (So, you, basically.)

Blue Valentine

3. Blue Valentine (2010) | Directed by Derek Cianfrance

If Blue Valentine is, in execution, an imperfect film, credit should at least be given to the fact that it is, nonetheless, an ambitious one. Ryan Gosling and Michelle Williams, as the couple Dean and Cindy, devote themselves entirely to the role. It’s a down and dirty picture of romance, showing the irresponsibilities, and disparate attempts at reignition, and the hopelessness of when that love is drained and lost. Cianfrance is also able to evoke the dizzying nature of falling in love as well. It is perhaps seen best as a portrait of two people that love each other but continue to hurt each other. And what could be more anguishing than that? It’s best summed up in the song Dean performs for Cindy on one of their dates, “You Always Hurt the One You Love”.

2. Eternal Sunshine of the Spotless Mind (2004) | Directed by Michel Gondry

There’s something magnetic about love. In a way, Eternal Sunshine is sort of like a futuristic, sci-fi version of Annie Hall. But, too much comparison would be a disservice to such an inventive film. The melding of the minds of Charlie Kaufman and Michel Gondry, the two trace just how impactful our experiences, particularly in love, can be. These experiences inform our very identity as human beings and the craving to connect emotionally to another person is amongst the most critical. Sure, sure, deconstruction of the Manic Pixie Dream Girl is all interesting, but the pathos and lucidity that Kate Winslet brings to the erratic and manic Clementine makes it one of her greatest roles. Meanwhile, the vulnerability Jim Carrey displays as sad sack Joel makes it one of his strongest performances. Is it heartbreaking because you see the dissolution of a relationship in reverse? Yes and no. What’s even more heartbreaking is that it suggests that, deep inside us, we will always yearn for emotional intimacy. Over and over again.


1. Celine and Jesse Forever (1995 – 2013) | Directed by Richard Linklater

Yup, I cheated, because I’m a big fat cheater. But Richard Linklater’s (for now) trilogy, comprised of Before Sunrise, Before Sunset, and Before Midnight, is as perfect an examination of love through its entire evolution as you can possibly get. As a triptych, you get hope, remembrance, and struggle. Julie Delpy and Ethan Hawke have practically aged with us, and with that, each film matures in how it views life and love, never becoming too cynical (not even Midnight). All three films glow with depth and gradation, each perfectly refined in their perspectives. As we follow Celine and Jesse walking down the treats of Vienna, Paris, and Messina, we can only dream of the kind of relationship the two have. We realize, though, that as gorgeous and “only in the movies” as it seems, the specificity of their relationship does not make it any less identifiable for any kind of relationship. The intellectual connection, the emotional intimacy, the eventual fallout: this may be their story, but it’s ours as well. All the sweetness and pain, it’s all so deeply human and authentic. The films all work fine as separate entities, but together, they make the most complete depiction of love ever on screen. Hopefully we’ll get to see them again in another nine years. Because, baby, we are gonna miss that plane.

6 thoughts on “The Masochist’s Guide to Valentine’s Day: A Bunch of Films to Torture Yourself With

    cinemafanatic said:
    February 11, 2014 at 4:15 pm

    after I saw Before Sunrise/Before Sunset at the ArcLight on Sunday, I came home and immediately watch Before Midnight. it’s really a trip to watch all three back to back like that.

      Kyle Turner responded:
      February 11, 2014 at 4:28 pm

      The Lincoln Center in NYC was doing a marathon in December, and I wanted to gooooo. But I had plans. 😦

    The Q Filmcast : Netflix Instant Reviews & Discussion said:
    February 11, 2014 at 4:39 pm

    Reblogged this on The Q Filmcast.

    Brittani said:
    February 11, 2014 at 8:15 pm

    Nice post! I really need to get around to seeing the Before trilogy.

      Kyle Turner responded:
      February 11, 2014 at 10:28 pm

      You really must.

      Kyle Turner responded:
      February 11, 2014 at 10:29 pm

      And thanks so much!! 😀

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