6 Unconventional Valentine’s Day movies (and 2 TV shows!) for an “It’s Complicated” world

A curated, non-judgmental, singles-friendly watchlist
By Esther D. Kustanowitz  Published on 02/12/2018 at 12:21 PM EDT

Are you consciously coupled? Good for you. But if you’re not, it’s worth reminding yourself that relationships are more challenging than most movies and TV shows convey. So in honor of Valentine’s Day snuggle up with your best pals, a body pillow or your sense of cynicism and enjoy these movies (and two TV series, if you’re looking for an all-day commitment) in honor of on-screen romantic partnerships that are more complicated than their treacly cousins.

Love Actually (2003). Wait, what? This is one of the most romantic movies of all time, right? Look at the stories critically and decide: which of these relationships is the most enviable? Then host a discussion as to whether any of those stories are actually love (actually). For instance, I love Colin Firth. But would a writer fall in love with someone who couldn’t speak the same language and basically cleans up after him? I mean, I could use help cleaning up, sure, but language facility is often a priority for writers, so I’m calling shenanigans. These shenanigans are also in my best interest, since if writer Colin Firth breaks up with Portuguese lady, then he’s available. For me. And yes, I know this was a movie that’s now 15 years old and that Firth is now 57. But my list, my fake reality.


When Harry Met Sally (1989). Since I always fall in love with my friends this is both the perfect film and also perfectly heart-stabby, if you’re into that kind of self-torturing thing. (And who isn’t??) Also, visit with the late, great Carrie Fisher in her role as Sally’s friend Marie. And if it still depresses you – “they found perfect love, why can’t I?” – then take some comfort in the fact that genius writer Nora Ephron wanted to keep her original ending, in which Harry and Sally break up, but stupid Hollywood always prefers the happy ending so that they can continue perpetuating unrealistic expectations, known in the industry as “making money.” But Nora knew what was up. And so do we. And I will never want that wagon wheel coffee table, but I do believe that Baby Fish Mouth should be sweeping the nation.


The Break-Up (2006). When I went to see this movie – about a well-meaning couple who cares about each other but just can’t make it work because of different communication styles – I found myself praying for an ending that was different than the typical “all is mended – happily ever after” ending. And while my prayers were rewarded, the women in front of me at the theater were visibly upset. (“That’s $12 and two hours of my life I’ll never get back,” one of them said.) They wanted the Hollywood ending. Which is fine, but I thought having a “romantic comedy” (a description that’s a stretch considering how mean the two are to each other at various points) with a realistic ending was so important to understanding how relationships work, or sometimes, don’t. Having more “romantic comedy” movies that don’t necessarily end in an organza wedding dress (organza is a thing, right?) is better for all the young girls out there, who might grow up with expectations regarding relationships that are a bit more sensible and realistic. I’m a huge killjoy, I know.

RELATED: Geeky gifts to get your Valentine’s (or yourself!)

Say Anything (1989). Think about most romantic comedies you know. About the girls who can’t quite get it together, who fall over and realize that the person who’s helping them pick up their papers/who hit their car/who is their nemesis/whatever is the one for them and they spend two hours trying to get them. Lloyd Dobler (John Cusack) is the flip of this: the high school student who thinks kickboxing is the sport of the future, who loves Diane Court, the school valedictorian. Diane is also beautiful, but Dobler doesn’t objectify her, because  beauty is only part of her package. Diane is smarter than she is beautiful, and she doesn’t have a lot of close friends; she loves Lloyd because he’s a little weird and awkward and because he’s a constant source of support (even if that support is a little awkward). He gives her his heart, and she gives him a pen, and we’ve all been there in some weirdly relatable, if not entirely literal, moment. There’s no subplot about either of them trying to be popular: they’re both trying to figure out how they feel about each other. The addition of Joan Cusack playing Lloyd’s sister and the late John Mahoney (who died just last week at age 77) as Diane’s loving but criminally flawed father, and little co-starring gifts (Lili Taylor as Lloyd’s friend, Corey, who has written many songs about her ex, Joe, who “lies when he cries”; Pamela Adlon in a small role as Lloyd’s friend, Rebecca) make this story a classic, even before Cusack lifts a boombox over his head. “In Your Eyes” is probably the only song I’ve never tired of, not for a moment – and I can’t guarantee it’s not linked to its presence in this film.

Teeth (2007). If you think sex is dangerous enough already – presenting opportunities for disease and heartbreak and disappointment – don’t miss this modern, horror-style exploration of the vagina dentata myth, in which a woman’s vagina contains teeth that could injure any man who attempts to penetrate it. It’s a folk tale that has versions all over the world (and you can read about them here). Question for a post-Harvey Weinstein world: what if the teeth could be trained to recede when desire and love are in control and to chomp down when a woman is attacked? Check out the trailer and then agree that none of us should ever date again.



Ingrid Goes West (2017) – This movie is ostensibly about a woman (Aubrey Plaza) who gets a little too invested in her friends, both real and virtual. But in a world where we judge so much of our own worth on how many likes we get on Instagram or other social media offerings, this story is both a cautionary tale and a tale of depression and mental illness gone untreated. A  socially critical story about Ingrid, yes, but also about the parts of ourselves that crave the attention, approval and love of others who we don’t really know, especially in the absence of a significant relationship. So make sure to like this story on all of your social media platforms!

RELATED: For additional Valentine’s Day movie picks, sign up for a Hulu account to see what you can stream now.


Sense8 (series, 2015-2018, Netflix). This weird, beautiful and ambitious series on Netflix from the Wachowskis (yes, the sibling directors behind the Matrix series) asks us to imagine a human interdependence that goes beyond the romantic, and even beyond the physical. The series is gorgeously shot in different countries and features actors/characters of diverse ethnicities and sexual orientations who are easy on the eyes. And don’t worry – being in different countries doesn’t mean they can’t hook up. For them, the world is a magic and cellularly linked realm where everyone is super-hot and good at fight scenes, and where a select few can tap into each other’s feelings, abilities and bodies no matter where they are geographically. It’s a little hard to follow, but will get you thinking about human connectedness, across language and geography, as well as faith, destiny and meaning. A lot to ponder, but in a way that makes us feel that maybe, even in our solitude, we are molecularly bound to other people.


Crazy Ex-Girlfriend (series, 2015-present, CW) – The cliche of the crazy ex is well-traveled. But as Rebecca (Rachel Bloom) points out from the beginning of this creative musical dramedy series, the situation’s a lot more nuanced than that, and so are relationships. Relationships are flawed, fragile and complicated, and the word “crazy” has different definitions. Rebecca is an unconventional woman, surrounded by people who could have been sitcom tropes (best friend, odd boss, etc) but all of whom have shown remarkable depth over the course of the show’s three seasons. In season one, Rebecca admits that California “happens to be where Josh lives, but that’s not why I’m here.”  Season two is about obtaining the love she quested after, and the theme song reflects her idea of herself as a girl in love who “can’t be held responsible for her actions,” and “when you call her crazy, you’re just calling her in love – BLAM.” Season three took a more serious foray into Rebecca’s mental illness and the underlying reasons she seeks affection, exploring four musical versions of “crazy,” as vengeful, romantic, dangerous and sexy. Overall, the series speaks to the importance of non-romantic relationships and how a search for affection may be doomed to failure until the underlying issues are addressed. We wonder why Rebecca makes bad choices, and then have only to look within ourselves to instantly understand. We also wonder why our lives aren’t underscored by highly-produced musical numbers with great choreography, and then realize it’s because Crazy Ex-Girlfriend has better writers and we can’t really follow choreography.

What are your favorite, unconventional choices for Valentine’s Day entertainment? Discuss below in our non-judgmental, singles-friendly thread.

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