“Love loves to love love,” or something like that. What is it about February 14th that brings out the grinch in me? The gender-normative stereotype reinforcing? The forced sappiness and craven branding of emotional expression? The sugar crash that inevitably awaits me after I eat an entire box of cheap chocolates at work that day?
Whatever it is that irks me, it’s not the passion or the tenderness part. I do love love, in all its cheesy grandeur and messy reality. So to help bypass my grumpiness about this “invented by hallmark” holiday, I made a list of my favorite romantic pop culture offerings for the season – movies, shows and musicals enamoured with love and passion, courting, sex and marriage, and break-ups too. So stay home and watch these, or go out and risk sitting next to that couple where one hides a ring in the dessert and the other ends up choking on it (just kidding, I’m pretty sure that has never once happened in real life).
1. For a hilarious portrayal of monogamy, marriage and kids that’s also terrifyingly real: Catastrophe
Rob and Sharon have an affair (he’s an American visiting London on a business trip), get pregnant, get married, and only then begin the process of getting to know each other and falling in love. Their haphazard approach to family life is a big part of this series’ charms, as is the warts-and-all portrayal of these two very imperfect but hilarious people as they fall for each other and try to work out all the details from there. Bonus points for Sharon’s filthy mouth (why is it so much fun when someone curses in an Irish accent?) and the sublime Carrie Fisher as Rob’s mother.
Three seasons of Catastrophe are streaming on Amazon Prime
2. For those tingly first love feels: The Office, the early seasons, especially Season 2, Ep 11 “Booze Cruise”
Oh Jim and Pam, why’d you ever have to get married, settle down and become so boring and predictable? Between the kids and the domestic strife, your story line really fizzles post-wedding, so I’ll choose to remember the early days of your love – Seasons 1 -3 mostly. Booze Cruise is an especially sweet Season 2 episode, in which these two are with other people (hey hey Amy Adams), and it’s obviously all wrong and we know they really belong together. Luckily their “will they/won’t they” fire still has a few more years to burn hot, with Jim only admitting to us (and himself) at the episode’s end that it’s Pam he’d rescue from the sinking ship every time.
The Office is streaming on Netflix.
3. For those exhausted, ‘ready to give up on love altogether’ feels: 30 Rock, especially the Valentine’s Day episodes and extra-especially “It’s Never Too Late for Now” (Season 5, Ep 15)

If you’re looking for a binge to get you through the 14th, may I suggest watching every Valentine’s-related 30 Rock, from Season 1’s “Up All Night”, where Jack goes on the ultimate bender after finalizing his divorce, to Season 4’s “Anna Howard Shaw Day,” in which Liz sneakily schedules dental work for Feb 14th, only to be rewarded by hallucinatory visions of her exes. Plus all the ones in between, plus one of my favorite 30 Rock’s of all time, Season 5’s “It’s Never Too Late for Now,” in which Liz tries to embrace spinsterhood, only to be whisked away on a mysteriously perfect romantic adventure. Also, spoiler alert, Emily Dickinson gets got by a hawk.
30 Rock is streaming on Hulu
4. For help coping with the insanity that is dating & relationship drama in 2018: Insecure
The hook-ups, the break-ups, the friendships, work stress – Issa Rae’s Insecure has its finger on the pulse of everything that makes being young and single in 2018 so damn complicated. In two short seasons, this show has already given us some iconic moments dealing with sex and love, all from the perspective of a group of black female friends navigating modern life in LA. The drama is real and the soundtrack is banging, but mostly I’d recommend this show to anyone because it manages to be so many things – sexy, funny, awkward, smart – all at once. Just like the fascinating women at its center.
Insecure is streaming on HBO services
5. For love that is weird and beautiful and sad (and also to help you cross off some Oscar nominees for this year): Phantom Thread & Call Me By Your Name
Ok, so this one is kind of cheating because you do have to go out into the world on Valentine’s Day to see them, but they’ve both been out for a while now, so the theaters shouldn’t be packed, and both are really fantastic. See Phantom Thread if you’re an old married couple – it’s a wickedly funny exploration of the push and pull at the heart of every relationship between two autonomous individuals who are also unquestionably yoked together by this strange thing called love. See Call Me By Your Name for a dreamy portrait of first love’s passion and heartbreak with a kicker of a final monologue from Michael Stuhlberg’s character that tells us not just to nurture the joy in love, but that feeling anything is a kind of salvation in itself: “if there is pain, nurse it, and if there is a flame, don’t snuff it out.”
Both Phantom Thread and Call Me By Your Name are currently in theaters
6. For the best love story (and Best Picture winner) from last year: Moonlight
A story of a love that spans two young lives, a love that evolves with the trial and tribulations of its lovers, a love that soars and triumphs. My full review here.
Moonlight is available to rent on Amazon Video, YouTube and Itunes
7. For art house cinema that revels in the hazy dream of love: the films of Wong Kar Wai
If you’re not familiar with the films of Wong Kar Wai, the Hong Kong Second Wave filmmaker, In the Mood for Love, Days of Being Wild, 2046 and Happy Together are all great places to start. In each, images and sounds swirl with cigarette smoke as people are thrown together and then torn apart by fate’s seemingly uncaring hand. Romance and ruthlessness combine to create an atmosphere of longing where the stakes can be life or death – Wong Kar Wai’s movies are just sexy, they’re lush and sensual and worth seeking out any time of year.
Wong Kar Wai’s films are available to stream on Filmstruck
8. For reminding you that being in love means inviting insanity into your life: Punch Drunk Love
“I have a love in my life. It makes me stronger than you can imagine.”
A Paul Thomas Anderson masterpiece (like there’s one that’s not), and an Adam Sandler performance so good it was hard to believe at the time, Punch Drunk Love is a trip alright – a strange trip from loneliness to love, from normalcy to insanity, and one there’s no coming back from. Along the way, Sandler’s Barry Egan has to battle what starts to feel like the entire world to win his love, but every shouting match and fist fight only brings him closer to bliss. Here PTA seems to be saying the pain and pleasure of love aren’t that easy to separate, or maybe even that one couldn’t exist without the other.
Punch Drunk Love is streaming on Hulu
9. For two stellar musicals about love’s ups and downs: The Last Five Years, Company
In The Last Five Years, a young couple moves from courtship to wedding day to separation and divorce, Jamie, the husband, starting at the beginning when everything was new and exciting and Cathy, the wife starting at the end with the agonizing song above. What you learn about them, and how their perspectives differed along the way, makes for an astoundingly complete depiction of a relationship. Rather than focus on one marriage, Sondheim’s 1970 musical, Company, deals with a handful of them, all among a group middle-aged friends with a long single person, Bobby, at the center. Bobby gets to see the pitfalls up close as the couples deal with boredom, infidelity or doubt and the we get songs that detail their tribulations (Sorry/Grateful and The Little Things You Do Together are two favorites). The music is brilliant and blistering and Bobby’s journey from cynic to a guy singing “Somebody hold me too close” is a love story for the ages.
The Last Five Years and Company are available to rent on Amazon Video and Itunes
10. For the one that will make you believe in love again (it’s also the one where Cher slaps Nicolas Cage right in his face): Moonstruck
Such a great romantic movie, I showed it my husband ten years ago, on our first Valentine’s Day together. I’ve probably seen it fifteen times, and it just never disappoints. It’s perfect. And it’s perfect even though Nicholas Cage does his damndest to derail it with a performance that doesn’t make sense on any planet. It’s perfect because Cher is perfect as an “old” spinster who’s going to marry a man she doesn’t love, because at some point, you gotta be practical. It’s perfect because there are scenes where people stare at the moon and cry at the opera and Cher’s faith in love is restored and somehow so is ours. And it’s perfect when Cage’s character declares his love with these words, the perfect ones to celebrate this weird and dramatic holiday with:
Loretta, I love you. Not like they told you love is, and I didn’t know this either, but love don’t make things nice – it ruins everything. It breaks your heart. It makes things a mess. We aren’t here to make things perfect. The snowflakes are perfect. The stars are perfect. Not us. Not us! We are here to ruin ourselves and to break our hearts and love the wrong people and *die*. The storybooks are *bullshit*. Now I want you to come upstairs with me and *get* in my bed!
Moonstruck is available to stream on Hulu and Amazon Prime