Doukyuusei 2
Doukyuusei 2 followed up on a game that essentially invented the free-roaming dating-sim genre in Japan. The player once again takes on the role of a final-year high school student during summer break and has a few weeks to build relationships with dozens of characters. Nothing holds his hand — he's given only a town, a calendar, and a clock that keeps ticking.
That is exactly the core of the gameplay: every location has its own schedule, and characters appear only at a certain time in a certain place. Moving around the map costs time, so planning the day becomes essentially a logistics puzzle. Conversations run through an action menu, and individual storylines develop gradually across the whole summer — a missed meeting can close off an entire branch for good. The sequel expanded the system with more characters, a more elaborate calendar, and smoother dialogue handling, so players get lost considerably less than in the first game. There is no single correct path: the calendar is short and the characters numerous, so the player must decide who gets their time and let the rest slide. That's also where the urge to replay comes from, since every run looks different and many scenes only appear if you're in a specific place at a precise hour.
Technically, this represented the peak of what ELF could do on the PC-98: colorful backgrounds of the town at different times of day, animated portraits, and an extensive soundtrack carrying the light, summery tone that became the series' trademark. Doukyuusei 2 had an enormous impact in Japan, paved the way for later school romances, received an anime adaptation as well as console ports, and its structure of freely spent time still shows up in raising sims today. It's an adult title and, without knowledge of Japanese, a demanding one, but as a historical milestone it's impossible to overlook, and its open structure is more interesting today than that of many linear novels that followed it.
Game 5 of 28 for NEC PC-98