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This OVA focuses on Isshiki Iroha's will to help Hachiman get closer to Yukinoshita and Yuigahama. She's seen Hachiman struggle, doubt his actions and desperately try to protect the thing he treasures so deeply, the service club. And that affected her as well(most specifically, Hachiman's confession about wanting something genuine), which she herself admitted. She's relied on him for everything and to her, Hachiman is the only person she can reveal her true feelings to, be who she actually is, he became a genuine friend to her, something that she might have passively been longing for. So now she wants to help him of ... her own free will, to protect his special place.

So she goes about it in her own Isshiki Iroha fashion, invite her senpai out to a date and learn about him, also make *him* learn about how to deal with girls better. That's not all however, because she herself also needed a break from all the stress and having fun with her friend is the natural thing she could think of. Two birds with one stone, truly a scary kouhai. And we see her deal with her own feelings while this all happens. What does she feel about Hachiman? For she herself does not know, and desperately tries to learn for her own sake. But the fear that taking him away from the other two also keeps her from crossing a line, so she still tries to avoid it(This is why she keeps trying to pretend that she doesn't feel anything for him). It's to be expected, she's just a high school girl who is only now properly learning about the relationships of people, and she's very much scared of breaking down Hachiman's.

This is where her character development is completed. She makes the hard choice and does the best that she could do for Hachiman, who's done so much for her. She becomes a cupid to strengthen the relationship of the main three, all the while pushing away the feelings she might have had for him, for their sake. This is welly portrayed in the very last scene of the episode, where she finally shows a genuine smile for a moment but with a tinge of sadness. But this is what she wanted, a genuine something, a genuine bond, and she feels that she's finally achieved it by doing something for Hachiman, whom she truly thinks of as her friend.

OVAS are always filled with fanservice and so is this, but even with 23 minutes and the theme songs, this episode managed to add a lot more substance to Isshiki's character, which was very much necessary. I'll even go so far as to say it's better than any of the episodes in zoku because of how rushed they were.