Harold And Maude

If There’s An Age Difference
There's certain things that only an older man or woman can teach you, (or indeed, a younger one—within reason, guys and girls) so everyone should have a May/December (or at least May/July) romance at some point. If that's the case with your current partner, celebrate the fact with Hal Ashby's glorious "Harold & Maude," in which Bud Cort's death-obsessed young man falls for optimistic 79-year-old funeral crasher Ruth Gordon. Once you get past the taboo-breaking nature of the premise, it's a remarkable and life-affirming picture, one that'll bring you to tears by the ending, but also considering raising the upper age limit on your OK Cupid profile by about 40 years.
If you'd rather watch a May/December romance with an older man and a young woman, why not try ANY HOLLYWOOD MOVIE.

Crazy Love

If You’re Crazy In Love
The truth is always stranger than fiction, and maybe you’ll feel better about your own crazy in love situation after taking in Fisher Stevens’ and Dan Klores doc “Crazy Love,”  about the absolutely batty Burt and Linda Pugach. Burt hired thugs to throw lye in Linda’s face, blinding and scarring her, but the pair somehow later reunited. Ladies aren’t exempt either, and you could make it a double feature with Errol Morris’ “Tabloid,” following the antics of beauty queen Joyce McKinney, who found herself in a British tabloid frenzy after kidnapping her Mormon missionary boyfriend for a bondage escapade back in the 70s. Just don’t get any ideas.
Silver Linings Playbook” is obviously the biggest and most recent version of this sort of craziness, and we’d also recommend Fatih Akin’s “Head-On,” though probably not as a date movie.


If You’re Into Tough Love
Look, we all have our own little peccadilloes and perversions, for better or worse, but the success of "50 Shades Of Grey" has revealed that far more of us are into, for want of a better term, domination/submission, that we were perhaps previously letting on. If you're in one of those relationship, and in lieu of the '50 Shades' movie (and in expectation of it probably being terrible), watch the excellent "Secretary," which doesn't sugarcoat the sub/dom leanings of Maggie Gyllenhaal's titular assistant and James Spader's attorney, but also demonstrates that it can be a totally healthy way of expressing love for each other. It's a sly subversion of the rom-com formula without resorting to cheap jokes, and it's pretty sexy to boot.
Not much to choose from -- we wouldn't recommend Michael Haneke's "The Piano Teacher" as a particularly great date movie, for instance. Maybe make your own?

Raising Arizona

If One Or Both Of You Are Criminals
Probably not a category that applies to you, but given the sheer number of movies about criminal lovers (we wrote a whole feature about them, even), we figured we should include something for those of you with spotty records. Even beyond those, we have plenty of recommendations. If both of you have criminal proclivities, we'd recommend Ernst Lubitsch's transcendentally good "Trouble In Paradise," which sees con artists Herbert Marshall and Miriam Hopkins fall in love, fall out, and eventually, get back together, as they trade witty, and wildly sexy, banter. If one of you wants to stick to the straight and narrow, "Raising Arizona" is the perfect pick: it might be the Coens' silliest film, but the relationship between Nicolas Cage's H.I. and Holly Hunter's Ed lends it an unexpected weight, and is pretty much a model of how to build a lasting relationship on either sides of the law.
"Out Of Sight," which might not have the happiest of endings, but is ridiculously sexy while it goes about it. "Bonnie & Clyde" could be described in much the same way.

Truly Madly Deeply

If You're Recently Bereaved
Firstly, our condolences. Secondly, what are you doing looking for advice in a movie blog? Thirdly, though many would go for "Ghost," watch its vastly superior cousin "Truly Madly Deeply." Anthony Minghella's first, and arguably best film, it sees Juliet Stevenson struggling to come to terms with the death of her boyfriend Alan Rickman, only for him to seemingly return as a ghost. Funny, deeply romantic and profound, the two leads have never been better, and it works wonderfully as a metaphor for the way that we idealize the deceased, and how it has the potential to cripple you moving forward.
It's more serious, and weirder, but Jonathan Glazer's "Birth" is a gorgeous take on a similar subject.

Let us know your own Valentine's Day go-tos in the comments section below.

- Oliver Lyttelton, Katie Walsh, Gabe Toro