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Darkest otome you’ve ever played?

I don't play many otome games, as I mostly spend my time watching anime, reading romance manga, and listening to otome audio dramas.

However, I recently played *Welcome Home*—a completely free R-18 otome game featuring a somewhat dark storyline and a possessive, *yandere*-style male lead.
 
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I finished playing Folie Fatale a while ago, probably the most craziest game I've played so far 😭 Every route is just full of crazy yanderes, not that I'm complaining.
 
Maybe Torikago no Marriage? It's an eroge, so the themes are a bit more intense. I really like it, but it's pretty heavy.
Sins of KALEIDO would be a perfect fit, were it not for the game's final route. And I really like its "bad" endings.
 
Black Wolves Saga, Folie Fatale, Hana Awase and MoshiKami off the top of my head. BWS especially... it's relentlessly miserable
 
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BLACK WOLVES SAGA. It's seriously dark. It was recently ported to Switch, and I tried playing it, but… it got so emotionally heavy that I couldn't bring myself to finish all the LIs and eventually had to tap out. It's really dark!!
 
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To avoid repeating myself and listing the same games—since "your friend" 🤣 wants a recommendation or a list—I'd suggest Kankinkon ~Sentaku no Hibi~; even the title itself is dark. It's a game that deals with themes like kidnapping, obsession, confinement, and so on. By the way, it's an 18+ title.