"10 Things I Hate About You"
"10 Things I Hate About You"

If You're Having A Girls Night In
Another one that is tried and true: what sets “10 Things I Hate About You” apart from the pack of '90s teen flicks is the fact that this film holds up. Seriously, revisit it sometime. Led by a headstrong performance by Julia Stiles, this adaptation of Shakespeare’s “Taming of the Shrew” is way more clever than it has any business being. Never forget that this film was the first time that the great Heath Ledger graced American screens, and he’s just so damn magnetically hot that you will mourn his loss all over again. The rest of the cast is stacked with future stars and quality character actors including a wee Joseph Gordon-Levitt, Allison Janney (THE BEST), and Gabrielle Union serving excellent high school ditz. Also the entire soundtrack is girl power alt anthems and Letters to Cleo. This film is engineered for an excellent girls night in.
Dirty Dancing,” obviously, because it’s fantastic, and because Patrick Swayze.

IFC Films "Weekend"

If You Have A Same-Sex Partner
Firstly, we hope it goes without saying that love is universal, and a same-sex couple will get the same out of any of the other picks here as a heterosexual couple, and a straight duo should enjoy these movies too. But you're totally within your rights to look for something closer to your own immediate experiences, and we've got a couple of doozies for you. If you're two guys, and you've been enjoying HBO's "Looking" recently (or even if you haven't), you definitely need to check out "Weekend," which hails from Andrew Haigh, who co-created the show, and directed multiple episodes. It's gorgeous-looking, swooning stuff, beautifully performed by Tom Cullen and Chris New, about a one-night-stand that ends up stretching on for a few days. Meanwhile, for two girls, we'd recommended "Show Me Love" (aka "Fucking Amal"), the deeply sweet and touching breakthrough from Swedish helmer Lukas Moodysson, which has all the passion and power of the recent "Blue Is The Warmest Color," but without the same problematic male-gaze issues.
"Keep The Lights On" is another recent cracker, and we'd also recommend Lisa Cholodenko's "High Art," though we're not sure we'd call either great date movies.

Breathless Godard

If You're On A First Date
We don't condone this—what the hell were you thinking, planning a first date for Valentine's Day? But the deed is done, so we might as well offer the best advice we can. You want to show off to your partner, let them know you have good taste. You don’t want to be dry and over-intellectual, and you don’t want to alienate them, in fear that they might be a philistine who is actually pretty great in the sack. So do what people have been doing for decades, and go for the playful landmark of the French New Wave. “Breathless” is swooningly romantic, both in content and style. You can impress your date and tell them which fourth-wall-breaking techniques are still used today. You can enjoy the black and white photography and reminisce about a time when movies were allowed to look differently, probably before you were born. And perhaps there’ll be a connection there; you’ll be the charming rogue Jean-Paul Belmondo, a notorious flirt and an outlaw of the heart. Or you’ll be the tantalizing, mysterious Jean Seberg, wearing your confidence on your short sleeve, seducing the camera with a wink and a nod. If he/she enjoys the film, there’s a very good chance the two of you could be partners in crime, flirts who get together and overdose on fun. But if your date LOVES the film, you may have a budding cinephile on your hand: grab them, pull them tight, and rifle your way through the Criterion collection together. 
You can also win cinephile cred from a prospective loved one with “In The Mood For Love,” or “A Matter Of Life And Death.” Though if they’re really the one, they’ll have seen both already. Ideally on 35mm in a revival house.

Human centipede

If You Want To Break Up
They hog the blankets. They spit when they talk. They won’t share the remote, and they’re loud talkers, the type that call attention to you when you’re out in public. There’s only one thing that they deserve: “The Human Centipede (First Sequence),” a sicko gonzo picture where a mad German scientist attempts to connect three living humans to the same digestive system. Hopefully, your partner will get the message that sometimes it feels like you’re suffocating, and other times it feels like you’re eating his or her shit. When the wonderful Dieter Laser pines for his beloved Three-Dog, hint to your partner that it reminds you of them. The movie is gross, gross, gross, especially because they pick and choose exactly what you get to see, leaving the grotesqueries to the imagination. But what if your partner gets seduced by all the medical equipment, the soft BDSM undertones, the relative cleanliness of it all? Then you have our permission to opt for “The Human Centipede 2: Full Sequence,” where all respect for the medical process goes out the window, and a 100-person centipede chain digests laxatives at the same time.
If they’re still with you by the end of all that, you might want to try “A Serbian Film.” Or go the other way, and pop in “Christmas With The Kranks”—not a single human hasn’t run screaming from that movie.