Shin Sei Yariman Gakuen Enkou Nikki The Animation

Yasuo is 45, freshly out of a two-decade marriage, and spending his nights drinking alone wondering where it all went wrong. That's a pretty bleak setup, and the show leans into it — this is genuinely a midlife crisis story before anything else. One night, a girl from the local St. Marian Academy approaches him looking for a paying companion, and that encounter pulls Yasuo out of his depressive routine in ways he wasn't expecting. The contrast between his worn-down salary-man exhaustion and this sudden jolt of youthful energy is where the story finds its footing. Based on a doujin visual novel by Orcsoft, Studio Seven's adaptation carries over the character-focused storytelling from the source material, and fans of the original game will recognize the tone pretty immediately. It's a single OVA episode, so the pacing is tight — it sets up Yasuo's situation and drops you into the central dynamic without a lot of hand-holding. If you've watched Okusama wa Moto Yariman or Saint Yariman Gakuen Enkou Nikki The Animation and appreciated that mix of character context alongside the adult content, this sits comfortably in the same space. It's not trying to be subtle about what it is, but there's enough of an actual story framing Yasuo's loneliness that it feels grounded rather than empty. Worth a watch if you want something from that Orcsoft catalog with a bit of emotional texture behind it.