The Big Sleep

We already mentioned that Real Men Love it, but didn't quite elaborate on why chicks dig it, as well: apart from the blisteringly clever dialogue and the fact that every scene is positively dripping with sexual subtext, it's devoid of all those things which traditionally turn girlier women off to otherwise great films. It's not horrendously violent (a few people get killed but, as was standard for the 40's, there's no blood), nobody curses, and the female characters are as intelligent as the male ones (even if they do need to be slapped around, on occasion). 

Without having to worry about all the gruesome murders that typically accompany the crime film, your date will be able to revel in the great chemistry between Bogart and Bacall, the subtle insinuations of the "horse racing" scene, and Bogie's neverending cleverness. Additionally, you'll get at least ten coolness points for showing her a black and white movie; by popping in a flick from before the 60's, you're telling her that you're the sort of clever, cultured fellow who doesn't subscribe to the modern, bullshit movie industry. 

Grindhouse

If you can get her to sit through the whole thing, Grindhouse is basically three hours of total Grrrl Power wrapped around hysterically over-the-top violence and a neo-retro atmosphere. The most badass character in the entire movie is a (somewhat) hot chick with a gun for a leg, and the entire last act of Death Proof basically concerns a bunch of chicks beating the shit out of a serial murderer. You'll love it because it's incredibly violent and stylish; she'll love it because it'll make her proud to have a vagina. Granted, you'll probably be yawning throughout the needlessly protracted conversation scenes in Death Proof, but she'll be totally immersed in them if only because that's how real women talk -- and unlike you, she's probably interested in hearing real women talk.

Moreso than any of the other films on this list, Grindhouse is also a great litmus test movie: if she likes it, then you know she's got the sense of humor and good naturedness to be a halfway decent partner and sync up with your tastes. If she thinks the whole movie is super-gross and covers her eyes when a helicopter decapitates a bunch of zombies, then she's probably not gonna be worth more than a month of your time.

No Country for Old Men

Hear me out: No Country for Old Men is so depressing, so violent, and so heart-achingly and convincingly nihilistic that anyone who watches it will want to be dead for at least a week after finishing it. 

This means that if you're watching it with your current girlfriend (do not even attempt to show this to a girl on a first date), then she will feel so incredibly hopeless that she'll have to have sex with you just to make herself feel better. No Country for Old Men just proves all those horrible things we fear to be true about the world: there's no such thing as justice, bad men can do bad things without achieving punishment, and innocent people die all the time. Your girlfriend will need to have slow, emotional sex with you (followed by a great deal of cuddling, whether you're into that sort of thing or not) in order to convince herself that the world isn't really like that -- that you can protect her from the meaningless violence of the world simply through companionship.

She's totally wrong, of course -- if Chigurh ever came for you or her, you'd be dead as motherfucking doornails -- but that momentary emotional weakness and yearning for companionship will pay off big time for the next few days.

Sympathy for Lady Vengeance

Sympathy for Lady Vengeance is a wonderful date movie for two reasons. Firstly, it's got the same girl power/ultraviolence dichotomy mentioned above in Grindhouse; secondly, it's esoteric and artsy-fartsy enough to make you seem like an intelligent, deep, complicated badass for picking it in the first place. Like all of Park Chanwook's films in the Vengeance Trilogy, Lady Vengeance consists of a strong anti-revenge message punctuated with scenes of absolutely horrific violence and sex. One scene in particular may well encapsulate the dictionary definition of "unfair" more than any other two minutes in film history, and definitely channels that same sort of "oh my god this is the saddest most horrific thing I've ever seen so do me so I can forget about it" vibe which No Country indulges in for its entire running time. 

Unique to Lady Vengeance amongst the rest of the films on this list, however, is how damn weird it often is. It dramatically shifts tone almost every ten minutes, its pacing is uneven, and there's a lot of symbolism that doesn't really go anywhere. It's the sort of movie where you'll understand what literally happened by the end, but not necessarily what every little bit means. This creates an opportunity for you to explain things to the girl you saw it with, which in turn makes you look like an intellectual, which in turn makes you look like you'd be a good lay.

Iron Man

Tony Stark was able to build your relationship in a cave. With a box of scraps.

You might not think a woman would be even remotely aroused by a superhero movie, and you'd be right save for two factors: firstly, that women find Robert Downey Jr really hot (assuming they manage to forget about him being an ex-drug addict and everything), and secondly, that Iron Man doesn't really feel like a traditional superhero movie.

Don't get me wrong -- a lot of the cliches are there (Tony loses his mask in the climactic battle, his archenemy turns out to be his closest friend, the creation-defeating small fries-archenemy three act structure is followed to the letter), but the tone, themes, and performances are totally atypical for the superhero genre. Downey Jr.'s performance essentially turns the film into a breezy, enjoyable comedy; both before and after Tony Stark's transformation into the Iron Man, Downey plays him as an effortlessly cool dickhead (thus arousing your date) and has great banter with each of the characters, especially Pepper Potts (thus setting the mood for you to engage in witty banter with your date).

She'll like the transformation story, the contemporary politics, and Robert Downey Jr. You'll like the explosions, and the fact that 99% of the women in the movie are fucking hot and in various stages of undress throughout its running time. It is, admittedly, the movie on this list least likely to get you laid, but it's a reasonably sure bet that your date will at least enjoy it and possibly allow you to sex her up anyway.