Wanderer: Broken Bed

An ordinary student who spends his free time gaming and watching anime falls out of the sky into another world, and instead of panicking he decides the sensible move is to conquer it, starting with every woman at the Cunningham Academy of Magic. It's exactly as self-aware about that premise as it sounds.

Once he lands, he gets enrolled as the Chosen One, which mostly seems to translate to unrestricted access to the academy's staff and student body while he figures out how magic and everything else works.

The loop mixes dating-sim conversation and choice-making with card battles and light RPG progression, moving between school locations to trigger quests, fights, and the relationships tied to them. Quest tracking points you to general regions rather than exact spots, so there's a bit of legwork built into finding what's next, and the game keeps a running save history so you can jump back to earlier points in the playthrough rather than being locked to a single autosave.