From the Princess Maker 2 Line Stickers
The Princess Maker franchise, produced by Gainax, is a series of raising sim games where the player character raises a daughter. These games have multiple endings depending on how you raise your daughter, with the endings where she becomes a princess by marrying a prince generally considered the "golden" endings. That said, there are several other endings, and usually at least a few other "special marriages" that are just as difficult to get as the princess endings. The first Princess Maker game was released on May 24, 1991, and there are five main games.
There was an attempt to translate the second game to English via a DOS port, but the company went down before it was completed, though you can still find the leaked version around. The first, second, third, and fifth games in the series all have official translations on Steam, but they also all suck, and the smoothed art for Princess Maker 1 & 2 both takes away a lot of the charm of the original games.
Aside from the five mainline games, there's an anime loosely based on the series titled Petite Princess Yucie, as well as a handful of spinoff games, including a board game, a puzzle game, a quiz game, and two mobile versions (one of which is defunct.)
CG from the Prince Marriage ending of Princess Maker 2
Princess Maker 2 was the first DOS game I ever played, and the game that got me into emulation and raising sim games in the first place. I remember my favorite ending was always the dragon ending, where your daughter marries the dragon youth. While it's not the only Princess Maker game I've played, it has a special place in my heart.
CG from the Dragon Youth ending of Princess Maker 2