The first thing I noticed is the aspect ratio is screwy, the picture looks like it's supposed to be 16x9, but it's displaying on vimeo as a 4:3 image, so I'm guessing that when the HDV footage was rendered out it wasn't rendered as anamorphic footage.
There's several inconsistencies with color and light levels between shots, the one in particular that jumped out at me was the cut from the two shot at 1:28 to the over the shoulder on the girl at 1:29.
It sounds like it was recorded with either the in camera mic, or a shotgun mounted on the camera, so it's not the best audio wise...
The attempt to light the "cigarette" or joint or whatever that was supposed to be doesn't really make sense, feels out of place, and he looks like he has no idea how to smoke.
It's also not terribly clear what precisely she's looking to buy, the one line that does state it is obscured by the noise of the chair being shoved.
Now, given the introduction you wrote here I expected much of this; yet I sat through the entire thing, which is more than I'll say for many shorts that get posted.
But, ultimately I guess I just didn't get the point you were trying to get across. It's stated that the film is about "teen pregnancy and the repercussions on the people surrounding bad decision making" but all I took away from it is that the guy is sick of this girl being an idiot and he blames her for making his friends leave (for college).
I would have liked a story that was a little more clear about the point it was making. Perhaps it is but given the description I didn't get that. I think a little time spent on lighting, even if just using a bounce card to get things closer to evenly lit, utilization of a tripod, and getting the mic closer would have been good investments as well.
For the most part, the shots are decent enough, though I think a bit of reframing, perhaps tighter shots, would probably have helped.
Anyway, food for thought.