They shop around like they would when playing a Bio Ware game, interacting with all the different available characters for too long and find they are suddenly railroaded along a generic path that usually results in a normal ending where you don't kiss anyone, or worst-case-scenario: a harsh death.
And I assure them not to panic from this seemingly premature decision, because dating sims are specifically designed so that you will want to see all the available characters, each attempt requiring its own separate playthrough on a different timeline entirely.
This isn't Persona 4, you can't get away with dating them all at once.
Dating simulation games like Hatoful Boyfriend most often take the form of visual novels, interactive text adventures with images and animations accompanying the branching story.
You won't be selecting every dialogue choice during your character's involvement with the game’s world, but you will be occasionally prompted to guide your hero or heroine along different paths, and depending on your prior actions these could result in good or ill.
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