Ore Monogatari!! is a series that looks unconventional at first glance but a second look reveals that it adheres to every trope of romance animes.
Plot arcs with misunderstanding as the foundation? Check.
Third parties? Check.
Impossibly optimistic leads? Check.
Unsubstantial episodic fluff? Check.
The characters are also not Ore Monogatari!!'s strengths. Takeo's unconventional looks for a male shoujo lead feels gimmicky. While it's true that he was ridiculed by the girls he liked back then, it was glossed over and the series portrayed him as a someone who is much loved by everyone. Swap him to a bland looking guy but retain his behavior and we will still get the same results. Suna is the most interesting character in the series for being observant while emotionally distant but was not given proper development. Yamato was not given much task aside from being cute and a doting girlfriend.
You cannot also rely on the show's humor as it borders too much on slapstick or events which require the audience's suspension of disbelief (Takeo's blissful ignorance of a 'university exclusively for females' and the restaurant incident.) There are also some episodes that are reminiscent of countless romantic anime before and bore the heck out of the viewers.
No major conflict occurred in this series which might shake Yamato and Takeo's relationship. What we received is their daily fluff that while admittedly sweet, is never substantial. Yet to dismiss Ore Monogatari!! as bland is also not warranted as it shows occasional moments of excellence.
The musical score of Ore Monogatari!! was one of the year's most moving and was used in perfect timing with emotional scenes. The voice actors also did their best (although Takeo sounds grating at times) to bring these characters to life. Ore Monogatari!! is also a rare case where the ED is much better than the OP.
When it gets its groove, it really stands out. In Ore Monogatari!!'s defense, it only took three episodes before Takeo and Yamato became a couple in the most awkward yet endearing way possible. The poignant scenes in this series are really moving and hit the right spot for shoujo junkies. The couple's technically second kiss counts as one of the finest moment of 2015. However, episodes revolving the side characters (Suna's sister, Shijou and Yamato's friend) and Suna are the better representatives of this genre for being believable and well-developed characters.
These flashes of brilliance do not absolve this series for playing too safe and for following religiously to the tropes which made the shoujo genre dull. So probably, maybe, it will be a long time before a series can dethrone Kimi Ni Todoke as my most favorite conventional shoujo series.