This isn't Persona 4, you can't get away with dating them all at once.
It’s a troubling view of human relations in general but it’s one that simple gameplay mechanics can handle.
So now we come upon the quantum conundrum of dating sims.
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.
Another hurdle I see people experience when starting out playing dating sims is that they spread themselves too thin.