Battle of Algiers

Welcome to the Dollhouse by Todd Solondz.

One movie that I've seen recently that impressed me was Ed Norton's 25th Hour. Up until I saw this movie I've been seriously under-appreciating Norton.

The People vs. Larry Flynt and, especially, Primal Fear are incredible first-coupla-movies for Norton. I've got American History X from zip.ca and I'm looking foreward to watching that in the next couple of days.

Gattaca? A bit of a downer, I guess.

Have you seen I Heart Huckabees? Seems to fit the bill.

I'd say no on Welcome to the Dollhouse if either of you were very outcast as youngsters.
I still can't watch it without getting really upset.

How about Secretary? Makes you think, and it's anything but a mood killer.

I Stand Alone

Yeah, I like Huckabee's (saw it twice). Movies like that would be great though (problem is I've seen a lot of them, like Royal Tenenbaums, Eternal Sunshine, etc.)

Ooh, Secretary! Yes, that's hot.

yeah but when he jerks off on her it's kinda gross. Nosferatu is hotter

I thought that part was hot as hell. I have issues, though.

I can't believe I just admitted that in a public forum!

I think the movie choices people are posting here tell you a lot about them.

Personally, I didn't know so many ladies liked "Secretary." I saw it and wasn't too enthused. Maybe I need a partner next time?

Secretary depends a lot on the lady.

I had tons of (female) friends who found it really traumatic/revolting. But then, it was a women's college.

Second the Wes Anderson idea; I had a great date experience with the Life Aquatic once. I'd put that one ahead of Tenenbaums for a date.

Avoid I Heart Huckabees. It was god-awful, and why watch it when, YES, there is Wes Anderson and the marvelous Rushmore and Tennenbaums to be had.

Secretary was kind of hot, but a boring movie to actually watch.

Hot movie that makes you think? Last Tango in Paris, and it steamrolls anything Maggie Gyllenhaal can get up to.

Henry and June

House of Angels (Änglagård)

If you've never heard of it, you must see it.

A small village in Vaestergoetland. Everything is turned upside-down when the local loner dies and his cottage is inherited by his unknown relative Fanny. She comes riding on a big black motorcycle with her androgenic boyfriend Zack, wearing black leather and spikes. The farmer Flogfaelt had expected that he could buy the cottage for a good price, but now it seems that Fanny and Zack will stay there. The village is divided into two camps, for and against them.

"I was very fond of Alice and Alice was very fond of me."

Happy ending.

Broken Flowers.

...or Wings of Desire.

Second the Broken Flowers recommendation. It's a movie that wasn't at all what I was expecting in a really interesting way.

edward penishands?

None of these movies seem like date movies to me. So many dark & depressing choices! (And your favorite Wes Anderson movie sucks! Unless it's Bottle Rocket.) Your favorite all-time movie != date movie.

I liked I ♥ Huckabees, and if you liked Waking Life, you probably will, too. But how about something brainless? My SO and I compromised on Kate & Leopold once; chick flick for her + time travel for me. Unless you've been dating for years, don't watch American History X or Secretary/Henry & June/Larry Flynt (unless she's that kind of girl, and won't mind watching something with sexual content in front of a relative stranger). Broken Flowers was not a date movie, either. Date movies are supposed to be silly, lighthearted fun, or maybe a little scary so she has an excuse to huddle up close. Or rent that movie you'd never watch in a million years and make fun of it. I realize you asked for movies that make you think, but a lot of these are straight-up moodkillers.

Get something classic Hitchcock, if you want to think (have you seen the remastered Vertigo?).

Dude! Rushmore is in no way a moodkiller! Rushmore has Bill Murray and Goddamned Miss Chang in it!

Oh, Eideteker, so much to answer for....

Have you seen Me and You and Everyone We Know? I just watched it last night--rather twee, and the mood/style of it reminded me a bit of an indie Punch-Drunk Love (which, if you haven't seen, is also a great movie to hold someone through), but I really liked it.

Back and forth! Macaroni!

My I humbly suggest Kiss Kiss Bang Bang? It's like someone mashed up Lethal Weapon with an episode of Entourage and then added a cracked out Robert Downey, Jr. I didn't expect a lot of of this movie, but I was blown away. It's an action movie, and a noir who dunnit, but it's funny as hell and...oh yeah, Val Kilmer plays a detective named Gay Perry because he's gay.

Worth your rental! (Might not get you laid, but there's full frontal in there)

House of Angels will melt your date. It's a very sweet, funny movie.

I'd suggest Apple Wars, but it never made it to video.

Maybe you missed these.
Sliding Doors- Personally I love Gweneth Paltrow. She plays a woman in two different timelines that diverge when she misses/catches a train. Romantic comedy.
Zero Effect- Bill Pullman as the worlds greatest detective and Ben Stiller as his side kick. With heart and an edge.
Twice Upon A Yesterday-2 timeline romantic comedy.