Oregairu is an anime whose premise screams "Look at me, I'm not one of those generic romcoms!"... and to a good extent it manages to keep the promise it makes with its audience, although not completely exempt from defects plotwise: it will surely be a pleasant innovation that will entertain the weary viewer of school and slice of life comedies, but don't expect a revolution in the genre.
Our male protagonist finds himself stuck in a club against his will, alone with what are meant to be his two love interests: nothing revolutionary, as announced; the two girls already met him in the past but he doesn't remember it: also pretty cliché. However, more than the situations, it's the perspective from which the situations are seen that is not easily found around: away with the flag-rising and the smiles in the light of the sunset at the end of a "we-don't-call-it-a-date-but-it-secretly-is"; now we get bitter thoughts and cynical smirks, and the actions of the characters are coherent with the whole mindset of the series. The plot is not new, and honestly it is also pretty average, but the plot is not the same as the story: it's how the plot is told that is the strong aspect of the show.
The drawings are good, the main characters are pretty detailed most of the time and the scenery is ok; there is nothing special about it, but it surely keeps up with the level that has been reached nowadays.
I never am particularly attentive to the background sound and to the songs, and this anime did not impress me in any sense in this direction; the opening and closing songs were just fine, but almost always I ended up skipping them to see the actual show.
The male protagonist is surely (and deservedly) the focus of the whole series: his wry and misanthropic monologues, his ruthless and caustic way of solving others' problems, ultimately his "loner-'cause-I-like-it" personality are completely the opposite of what we get so often from the nice MCs that we always meet in the average romcom, and it's in a word refreshing; this does not avoid in him some stereotypical helplessness, that actually arises from his own cynicism: he doesn't see the hints of romance around him exactly because he can't help but liquidate the matter as the false hopes of some random popular high school guy. Still, he surely has an appeal to many viewers (including me) who will identify themselves more with him than with the usual male protagonist of this kind of comedies.
The other characters too have some depth and originality in them: the two girls in his club are more than one-dimensional stereotypes, especially Yukino, whose not yet completely explored background has still much to offer for the second season. As for the secondary characters, they're likeable, even the ones that could easily fail (like the big chuunibyou and the girl who nosebleeds at BL); what I found appealing is that there really is a group of characters (Hayama's friends) that falls into the standard behaviour of romcoms, but it clashes so hardly with the harsh eye of the protagonist that it's still interesting to watch.
I have seen a lot of generic comedies, and I surely like this genre (otherwise I wouldn't have arrived to watch so many of them). But this particular anime captured my attention for the new direction it took, which deeply changed the way the story was conducted with respect to what it is to be usually expected: because of this, I easily spent a whole afternoon enjoying this series in one sitting, which is a rather good indicator of the way I felt while watching it.
Oregairu is certainly an experience that's worth doing, both for those who aren't usually fond of this genre (since they'll find themselves with a more realistic viewpoint on what school life is) and for those who have seen everything in the pretty uniform field of romcoms (since they'll meet an original MC and a refreshing perspective on those same experiences they've seen so many times).