Mysterious, slow movie with some young dudes trying to behave like black guys

I watched this movie a few years ago, it is in colour… can’t really say which year it’s from, but I’d guess newer than 2000. The language is English. Unfortunately I barely remember anything of the plot, maybe because I found it confusing – in some way a bit similar to Memento, but without the rush, violence and, most obviously, time reversal.

One of the main male characters is – I think – curious about the life of a female (I think) character, for some reason I don’t remember. There was a night scene of him watching her from the window of a multi-story building (in which I think he had rented an apartment for that very reason) and following her on the dark street when she leaves the other building, but he loses her shortly after (she unexpectedly gets picked up by a car I think).

The most vivid (and funny) memory I have of that movie is of a few (3 to maybe 5) young white guys who’d hang out (at least once in front of a supermarket) and share in their desire to look and behave like black guys. It’s a bit hard to describe, gangster-rapper style. They’d listen to rap music, wear hoodies and gold chains, drive big bulky cars and talk about meeting actual black people in real life. It still brings a smile to my face.

This is, however, not the main plot of the movie I am trying to find, but rather a little sub-plot. Actually, I have the horrible feeling the whole movie doesn’t really have a main plot as such but may be just an interesting collection of loosely connected or even unconnected stories, of which the white boys/black guys one is certainly a very short and probably rather unimportant one.

The whole movie has a cryptic, slow tone, maybe even melancholic at times. Even the “funny” little white boys/black guys sub-plot has some melancholy to it because the boys know they’re not really black and may not ever meet any “gangster rappers”, let alone become like them.