As a piece that primarily revolves on the date between Iroha and Hachiman, you don’t get a lot of backstory here, it just drops you in immediately. That does not negate its charm though, we get to see Iroha in her natural element; a forceful, yet sly demeanour that puts full effort into getting Hachiman to really enjoy himself. We don’t have any distractions, it’s one-on-one, as a date should be and provides some very entertaining and memorable results.

From the initial get-go of Hachiman choosing to go to the movies, giving Iroha a movie to watch alone while he enjoys his own and then to meet up afterwards really shows how Hachiman’s mind works. He’s constantly in battle with himself for just a comfortable existence. He’s more than happy to go about doing things on his own than to do so with others. This is in sharp contrast to Iroha’s persona, where she is going out of her way to get attention, to push the boundary between charming and cunning. It really sells their banter to one another, an often crude, blunt and tease ridden relationship.

The ping-pong scene after is one of my favourite scenes in all of anime. It’s the very reason I chose Iroha over both Yukino and Yui as best girl for this series. It’s due in fact of the sheer relentless onslaught of Iroha’s actions of being one step ahead of Hachiman at all times. From distracting him (both deliberately and inadvertently with sleight of hand and choice of clothing respectively) her charm here far extends her screen time in the 2nd season. You really see it first hand here in a more intimate way. She acts genuinely only to him and he’s doing the same with her. It’s just a fresh take on the cliches that we’ve come to know in the genre, let alone the show.

It also wouldn’t be a real episode with Iroha without touching on the on-going gag of her rejecting him at one point. And I can safely say that here, this is by far the best scene she does so in.

"I’m sorry but you can only do that when hanging out a couple more times."

Previous outcomes would be her just scoffing at the notion of something happening. At this point, Hachiman’s odd charms might be softening on her. We also get Yui and Yukino’s extreme jealousy when they pose their results to them the next day, another gag that I personally can never get tired of.

The 2nd half of the episode actually revolves around both girls doing the same activities that Hachiman did with Iroha on the following weekend. It’s a fun little montage that serves as a comparison to show how really different all 3 girls are to interacting with Hachiman. Add in continuing gags of Yukino’s lack of bust size and cat and dog contrasting metaphors, and we have another episode that pads ammunition towards which girl will win in the end. The episode ends with a heartfelt photo of the 3 members of the Service club. I wish what was covered here was more than one episode, but even so, the 30 minutes of quality content really shines through. The coyness of Iroha really provides a nice buffer to the tsundere attitude of Yukino and the bubblyness of Yui nicely, and I can safely say this episode cements Iroha as a nice 3rd choice to Hachiman, even if there clearly is an obvious endgame in mind.

I could wholeheartedly say this is a mandatory watch to anyone engulfed with Oregairu already. An OVA that caters to a specific character, but in reality shines light on the differences the 3 mains have with each other as well. If one episode can do that with fantastic pacing and great character development, it's definitely something to not overlook.

(+) - Dynamic of Iroha & Hachiman
(+) - A strong focus on character development
(+) - Yui & Yukino's supporting roles
(+) - Animation on par with 2nd season, i.e spectacular

(-) - Could've used more than one episode