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There are some people who dislike this disjointed storytelling style, such as those found in transmedia properties, so these types of games may just not be enjoyable for them.
999: Nine Persons, Nine Hours, Nine Doors and Virtue's Last Reward director Kotaro Uchikoshi spoke of his attempts at harnessing the player's experience and perception of a game's story during multiple playthroughs.
If you walk off the path, you'll be pushed back onto it. The systems in these romance-focused visual novels are usually not robust enough to support complex social sims, they're more like long and pretty choose-your-own-adventure novels.
The player must accept their limited role in these spaces and do what they can in order to dig the interesting bits out of these games’ juicy narrative databases.
They are built to anticipate and encourage that style of play.
Many Western players new to the genre miss out on that fundamental aspect of the experience, writing dating sims off as shallow and basic after dipping their toes in.
Many folks never see Hatoful Boyfriend subtly transform into its final revelatory route that blows everyone's minds.
Both approaches have merits, but I enjoy digging into a dating sim and seeking out all the various endings and full gallery completion.
As you repeatedly go through one of these games with your different romantic focuses each loop through you'll notice that things in the story can change pretty drastically after a designated turning point, depending on how that particular sim is laid out.
Characters who are hale and hearty in one route will up and die in another, enemies become friends and vice versa.
But when playing dating sims you are actually being quizzed on how much you know about a particular character you’re after, either learned through attentiveness or knowledge of tropes.
Approaching the games in this manner leaves one much less disappointed when they don’t deliver a true vicarious romance experience.
Another hurdle I see people experience when starting out playing dating sims is that they spread themselves too thin.