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Pre-review:
I’m currently reading the manga and reached ch.163 (prior to the events which this OVA covers from the manga). Words can’t express how disappointed I was as I watched this. I wanted to experience Kenshin’s past in anime format w/out spoiling myself from the manga because I generally prefer anime over manga as it is more immersive and engaging. Most of my criticism will be due to the short length of this flashback. (I know it’s like 15 ch.in the manga, which is short also, so the manga isn’t excluded from this critique)
Before going any further I will SPOIL some of the chapters featured in ... the manga and the ENTIRETY of this OVA:

Characters and their motivation:

Every character featured in this OVA –aside from Kenshin- are bland and uninteresting. Now, let’s talk about the main cast (will be further explained in the writing section). Himura Kenshin is first presented as a child who went through a tragedy at a young age when seeing all of the three women, who bought him as a slave and took care of him after his parents died, get slaughtered by a group of bandits and got saved by Hiko that’s when he develops an ambition of saving the weak from the oppressive thugs by learning swordsmanship.
Tomoe, this bland character has no interesting quality in her at all. Her only existence is to act as a foil one for kenshin’s main story of atonement, and has two purposes to achieve which is to act as a love interest for Kenhin and to get revenge from Kenshin who killed her future husband.
Now the supporting cast, Enishi is Tomoe’s brother who hates the battousai because he ruined the future life of his sister so he wants to get him killed. Honestly, Tomoe’s death ruined Enishi’s character for me because Kenshin didn’t kill her deliberately or something of that sort, he wanted to kill an old man and she jumped in so she got sliced meaning Enishi’s reasoning now to kill Himura is non-sense and even if it is justified why didn’t he kill him when they were in the same place and (how) didn’t Enishi saw Kenshin’s remorse due to Tomoe’s death. Katsura Kogorō has nothing going for him nor the spy and I don’t even know why he betrayed them. Hiko, Saitou and the others play their role perfectly (JK) -a master and a formidable opponent against Kenshin- nothing more and nothing less.

Writing:

Beginning:

It starts out as I said in the character of Kenshin and it sets the tone for what this OVA will go through and it achieved it perfectly.

Story arcs:

There is only one which is the love relationship between Tomoe and Kenshin and that’s a problem, first there is no more than that and second it’s not executed as well as many people claim it to be. First point: It was a wasted potential that there was no training arc b/w Hiko and Kenshin, which doesn’t add any depth to the relationship b/w the master and his pupil nor do we learn anything that happened to Hiko in the past to what led him to be a swordsmanship to let us care about him nor does he have anything interesting in his personality which makes stand out so he appears as a plot device just to make Himura strong, whether it is in the Bakumatsu or the Kyoto arc. Another story missed out is that of Saitou’s group we never spent time to learn their motivations and ideologies other than being police which serve as opponents to the Ishin shishi. Now the main focus story of this OVA, the Love relationship between the main characters. What makes it so weak is that there is no redeeming factor for any of the two for each other, for example what makes Tomoe love Kenshin? IDK, it’s not like he saved her in any shape or form, it’s quite the opposite he killed her childhood friend who would later on become her future husband the next month of his assassination. The only thing she finds good about him is that he is good at heart but because he has been as an assassin tool for a cult to achieve their goals, that’s why he became like this…. you know Tomoe just because you sympathize w/him doesn’t means he is excused for what he did against your childhood friend. As for Kenshin, this boggles me even more, why did he love herr? We got 2 eps of them barely talking to each other and she didn’t offer anything useful to Kenshin like giving advices or anything and the point where he mentions that she helped him to get a new way life and become less of a hitokiri and more of a normal man. No you (Himura) dummy, you only got to see that life because of the downfall of the Choshu clan that made the leader ask of you to go away from Kyoto, and the businesses you made as earning money was an advice from the spy and he persuaded you to sell those medicines and not Tome. Farming plants as a way to live your new life, is a thing you suggested to Tomoe and she agreed on doing it. Kenshin you already were thinking of not killing people even before you knew Tomoe so that change of you that you claim it is thanks to Tomoe is a lie.

Characters dialogues/interaction:

It is a mid one honestly. You had those big words when those military swordmen talked to each other and kenshin’s interaction with Tomoe which was hella boring since you don’t feel the chemistry b/w those two, they have the same dull faces when they hated/didn’t care for each other and when they loved each other. In addition, there was kenshin’s monologues which honestly are the saving grace of this category.
Character development:
Kenshin’s development is extremely well-done. We always see him have a psychological conflict within himself, he always wanted to save the weak from oppressive people so he got into the Ishin Shishi (after he got proposed by Katsura Kogorō )to create a new age of peace but the way he do things is contradictory to his beliefs since he kills a lot of people he is assigned to assassinate, and he always had this feeling of not fulfilling what he wanted to achieve actually and at the end he realizes that what he had done was wrong and he is in the path to atone for what harm did he cause to a lot people’s lives.
Tomoe…. Has no character development aside from hating to loving Kenshin. And I already discussed that she is uninteresting

Ending:

The ending was good on its own but the pay off was not good for me. As Kenshin finishes his last mission, he goes off in his path of atonement.
World building:
During my read in the whole manga we never actually see the actual relationship between the shinsengumi and Ishin Shishi aside from being enemies or anything related to this setting, so I thought we would get-at some point- a good flashback about that and it would be this. Granted it’s a historical setting so if you don’t know about the Bakumatsu history -like me- then you are screwed. You are expected to go into this knowing that, so I can’t discuss it since IDK much about it, but that doesn’t excuse the OVA to go half-assesd about it. You don’t ever understand why the Ishin Shishi do what they do and why against the government.

Production/Presentation:

This is one of the best production of Anime I’ve seen. The musics were fire and hits at the right places, the animation is superb. No complaints

Enjoyability:

I didn’t really enjoy it too much. Since the relationship between the MCs aren’t compelling and their interactions are borderline boring and it is the only thing we had (as a story arc), everything else was kept at a minimum.

My Final thoughts:

I was really disappointed with this OVA seeing a lot of tens and a lot of people praising the love relationship between the MCs and I think it is a mediocre one. If you ask me what anime has a good love relationship, I would say Okabe and Makise (from Steins; Gate) is one of them.

I will start by saying that this anime is best anime with a school setting on it. My purpose of writing this review is that I didn't find any review that matches my perceptions on this anime.

This show at first hand seems like a generic harem rom-com series, just by reading the synopsis, but let me tell you that after watching the series, there is a sense of realism that occur in each episode that makes you say that this event does happen in real life but it is something not a lot people talk about but they know deep down they act in that ... away. Now I will start reviewing by writing about the characters, then the setting/the world of oregairu, some events that happen in it so that I can elaborate my statement (major spoilers will be noted in a section so you could skip it now until you have finished watching this show) and finally theme that oregairu tackles.

The characters: as I mentioned before that oregairu seems like your generic rom-com, that's because it introduces a cast of well-known stereotypes; a loner (but a special one), a girl that thinks she is a superior being and dislikes the MC at first then like him, an air-headed girl that doesn't accomplish anything and act in an annoying way. However, most of the characters have depth put into them and their personalities don't change that much that fast which makes it realistic since there is no human who try to improve himself or change his personality and get changed in a blink of an eye.
-------Minor spoilers for the cast I guess...-------------------
Hachiman Hikigaya: he was constantly getting laughed/shunned at in school that made him have a depressive look and tone in his character and doesn't get in any kind of relationship because he feels it's pointless since it always ended up him being sad or lack self- esteem, and you know from the first episode that Hachiman really despise dishonesty that the people express within themselves which also make himself distanced from people. Now, his way of solving problems (when people come at the service club and request them to solve their problems) are reasonable in theory but in practicality (some of them) are devastating since it will always result in people hating him, he often does it because nobody offers a better solution/ agree to act on his ways and he says that he doesn't care for these people's opinion on him but deep down he does these things just because no one will ever do it so he sacrifices his reputation for the sake of maintaining people's lives even if he doesn't acknowledge it himself.

Yukino Yukinoshita: She is inherited with wealth and a beautiful face that made male students shift their focus and like on her which, in return, caused the female students to become jealous of her and made her life a pain in the ass. She says people always get jealous of other people because of their accomplishments or inheritance and that annoys her a lot. She say that she didn't choose her face to be like that meaning that if you want to be respected you should try to do your best to achieve it and that's gotta be one of the many good lines presented in this show. She often tries to show off that she is a strong self-reliant girl but on the inside she always have an inferiority feeling due to her sister and Yukino despises her family since she live alone and hates the moment she meets any of her family member. She always tries to solve people's problems but ultimately gets turned down by Hachiman most of the time; because her way of doing things in practicality does no harm to themselves, it also results in no effect (or not a major effect) but her opinion isn't entirely invalid, it just when Hachiman presents his arguments he always have the upper hand.

Yui Yuighama: I have nothing to say about this character because she literally have no effect in the story, she doesn't offer neither an argument nor a valid reason for as to why act upon it, what's worse she doesn't even tries to help the request-ers, she just spits her opinion to make herself look like she is participating but at the end of the day she relies on Hachiman to do the job and blames him if he did something that displeases her. she just joined the club to get close to Hachiman and nothing else. I wouldn't be bothered by her that much if she was a supporting character but that's not the case.

Hiratsuka sensei: what makes her so awesome is that she acts like a real teacher; she often tries to give advices to our MC to improve his problems, in addition, she offers him a bit of her wisdom in life since she has more experience and she cares to make Yukino and Hachiman became out of their lone life to a social one. What makes her even better is that she appears occasionally making her scenes all the more better.

Haruno Yukinoshita: Now we come to my second favorite character in this series. She is a phenomenal one. Every scene she appears in she dominates, her presence is always calm and intimidating, even Hachiman himself doesn't want to be next to her because she always teases him and she bosses everybody around, never ever does she lose her cool while speaking and sometimes you can't tell if she honestly hates her sister or not because of her action. Sadly, this woman doesn't get mentioned in any review I've read (one of the reasons I'm writing this review). I honestly want to watch/read a spin-off series where Haruno is the MC of that and it would be AWESOME!!
although bae I always wondered this question to myself "why doesn't she focus on her college studies rather than wasting her time w/highschool students?) but whatever who cares, she makes this show extremely entertaining to watch

the other characters are generally generic and don't have a significant part in the story except Hayama in the 2nd season(which becomes one of the best characters in the series), Kawasaki Saki act like a real person and it is a shame that she doesn't get any character development nor more screen-time other than her episode introduction, ep 5.

-------------------------------------*******Spoilers alert****-----------------------------------
The setting: this is the only show I've seen that has more diverse settings and at the same time doesn't feel forced or weird. You've got the school setting in which the service club do their job and you see what the students do in their free time which the world seem more immersive and realistic. In addition, you've got school activities which ranges from cultural festival to sport festival or even normal sport periods in which our MC plays tennis with Yui (and proves her uselessness here and gets injured so Yukino substitutes her) against Hayama and Yumiko. moreover home setting which is done better than any series I've watched where we see how Hachiman really is a lazy introvert who represents us by always not answering the phone because he doesn't want to engage with people or lie saying that the battery is low and even when the summer vacation ended he said that he wants two more months, like c'mon don't say this isn't a good representation of a slice of life. Moreover, of course a person needs some fresh air so what do Our characters do? they go to malls for shopping or cafes and have a nice chit-chat with other and to annual Japan festival (the one where Haruno, Hachiman and Yui meet each other) and also a summer vacation trip where our cast enjoy being with each other and try to help the children.

the events(problems represented in service club and cultural festival arc):
Not all of the issues requested are amazing but some of them have actual depth when you relate it with the slice of life genre and the best one is gotta be-in my opinion- The case represented in ep4 where Hayama 's are being portrayed as delinquents. As Hayama requested this to be solved, Yukino (as I explained before hates people who misbehave like this to down someone or make someone suffers) is committed to expose the person who caused so that he/she learns their lesson and feel ashamed of themselves and the line that she says one line that is so true about these type people. However, she can't do much since she is in another class so she relies on Hachiman and useless Yui to solve this. However Hachiman doesn't want to make people suffer so he finds a way to make the culprit remain unknown, so as the Hachiman said , 70% of our communication can be understood/seen by body language and so the problem here is that Hayama's friends are 3 students and soon they will have a workshop visit where classmates will be divided into a group of 3 students, so by that one of them will be left out, but every one of them want to be with Hayama so they the only choice left is to spread ill rumors about them to get one of them as they really don't relation with each other, other than being a friend of Hayama which actually had me sometimes feel awkward in a situation where our main guy left out and left us alone but this problem could be solved by letting them engage in some kind of activity alone so that a seed is put in them and eventually it turns out to be a tree (becoming friends). This review is way too long so I will say this the cultural festival is the best arc of the series and you will know why

Moreover, the best or second best aspect of Oregairu is the Mono/Dialogue (Especially the monologues and MCs interaction with Yukino and Haruno). Never Once I felt bored When the characters talk talk to each other since the Mono are interesting which views Hachiman opinion on matters which deepens his character and the dialogues always gets back and forth and becomes like a debate (Yukino and Haruno) and Hachiman speaks facts whether you like or not.

The theme this show tackles on is dishonesty. People always tries to make themselves look good by being dishonest (for ex. Giving your opinion to the majority side of people even if you disagree w/that opinion yourself) whether because you don’t want to break someone’s heart because of the relationship you had built up till now or because it would ruin your reputation among the people surrounding you, but continuing living by that will lead you to have a problem in the future since you didn’t discuss the issue seriously or properly and keep avoiding the matter until there is no way to turn back and this show perfectly demonstrates that which makes it so great. I’ve rewatched S1 like 2 times and S2 like 3 times, and I couldn’t bored.

Thanks for reading :)