What should I watch on a fifth date?
Classic and unconventional romances for Valentine’s Day and beyond
Do you remember what you watched on your first movie date? Or even which date it was? Mine with my husband was the second: Alphaville, after whiskey and grilled cheese at a bar that only served that. It was cold out, and we were just looking for something reliably good and perhaps hinted at our tastes at least a little.
By the fifth date, things are different. By then, you’ve already established the obvious. Now it’s about small, telling things: do they squirm in discomfort? Laugh at the wrong moments? Sit quietly with longing or chaos on screen? Perhaps it isn’t date five (I’m out of the dating game now, remember.) Call it whatever stage you like; the point is, it arrives. In any case, here’s what to watch on February 14th, depending on your mood.
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An actual romance
For old-soul romantics who want wit and lift, I cannot recommend Elaine May’s A New Leaf enough.
For high-intensity feelers, a competent, stormy Brontë adaptation like Cary Fukunaga’s Jane Eyre will absolutely do the job. If watching In the Mood for Love1 feels too exhausted or sacred, Wong Kar-wai’s Happy Together offers a more bruised (and gay) vision of repetition and longing, and a love that doesn’t quite stabilize.
Love & Basketball—Gina Prince-Bythewood’s Compton-set decades-long romance and coming of age drama—is too good for me to mar with any sports/on-the-court-related puns. Leo Carax’s Lovers on the Bridge is wilder, and that makes emotional extremity feel not if not reasonable at least a little glamorous, as do all things French, including Juliette Binoche, who stars. It also happens to be playing at Metrograph.
Ethan Hawke movies
If you’re not a fan, skip by all means. But I think he’s having a moment, or just on my mind after watching The Weight at Sundance, Blue Moon, and The Lowdown last year. A number of people in my life just saw Training Day for the first time, which would work well too, since it features a now-classic on-screen pairing. The movie though squarely belongs to Denzel.
There’s also The Black Phone movies for something masked and terrifying, or—my pick—Alfonso Cuarón’s 1998 Great Expectations, which I like in earnest. Gwyneth Paltrow’s cameo in Marty Supreme felt like a tease, so you can remember why she’s a good nepobaby by watching her as Estella, swanning around in slinky ’90s Donna Karan, most notably that “bottom-of-the-pond” green two-piece, conceived long before The Strategist turned it into a shoppable aesthetic.
The fifth-date movie isn’t about impressing anyone. If you hold Before Sunset too dearly, don’t show your date unless you’re ready to confront internal panic for the entire runtime and a potentially unenthused reaction. Juliette, Naked, though, is lower-stakes, and you can talk through it, if you must. Hawke sings The Kinks for Rose Byrne. You could do much worse.
Conversation starters
These are movies that act as social lubricants or intellectual stimulants; they give you something to debate over fries and martinis in a civilized manner. Hyped movies, documentaries, and anything buzzy are pre-loaded with discourse. They don’t have to be romances either: Cronenberg movies make the best date-night movies, imo, and Sirat (now in theaters) delivers a full-body experience.
The newly released Pillion may prompt fewer conversations about kinks than about your exes and first loves. If probing sexual latitude while immersed in exquisite imagery is the goal, try the sapphic and velvet pleasures of The Duke of Burgundy and Almodóvar’s Tie Me Up! Tie Me Down! Just don’t watch Babygirl; these are your alternatives.
Something serious to take it to the next level
This is the dangerous category of movies that might make you reconsider your relationship rather than deepen it. If you’re trying to define what you are to each other, ideally, it doesn’t require a third party to mediate. There are gentler ways to have that conversation than watching two other people fumble through it for an hour. Still, the canon is ready.
Paul Mazursky and Noah Baumbach have built entire careers out of romantic negotiation and familial brinkmanship—dramas of people sitting on couches and articulating their disappointments with unnerving clarity. FWIF I’d pick Mr. Jealousy (on TUBI!!) for a lighter touch, plus it features a lot of walking and talking around Manhattan in the winter.
Less grounded in realism, Nine Months can help you broach the subject of kids head-on. As someone not particularly interested in them, I found this movie a hellish vision of life and of societal norms. It’s so funny to me that at the time, Hugh Grant’s arrest for soliciting a sex worker had so many people outraged to the point where Gene Siskel said in his review that the event would limit people’s enjoyment of the movie.
For anti-romance types
Some people would prefer not to participate in the prix-fixe capitalism of Valentine’s Day at all. In that case, you can lean one of two ways: toward cynicism, or toward something that smuggles hope. You’ve heard me talk about Catherine Breillat movies and Albert Brooks’s Modern Romance, about a man unexceptional in every regard except self-confidence, of which he has enough to power a small town—perhaps a prerequisite for this screenwriter trying to survive Hollywood. It’s also currently on TUBI. In the second bucket, I would put movies about all the socially intolerable people who nevertheless find connection, like Minnie and Moskowitz. The trick is that these movies have a lot sentimentality-factor.
Claire Denis manages to thread the needle with Let the Sunshine In, starring Juliette Binoche, who plays a middle-aged divorcee cycling through a dispiriting parade of not-great men. The film performs a neat trick, allowing hope and humiliation to coexist without resolving either.
There’s a generosity of spirit that also runs through James L. Brooks’s As Good As It Gets. Jack Nicholson plays a racist, homophobic, antisemitic dog-hater with OCD, a truly terrible human for whom affection is an acquired skill. Growing up, this movie, which stars Helen Hunt with a hint of outerborough accent, aired constantly on TBS, which is perhaps why I thought it would be breezier and less weighed down by depression. The first scene startled me with its meanness (I also laughed, really loud), and the last unsettled me in a different register. They don’t make them like they used to.2
Except they kinda did. Brooks’s Ella McCay.
I forgot to add GATTACA in the Ethan Hawke section which is where that first image is from
Another earnest Great Expectations fan. Cannot resist Alfonso x Ethan x green.