

Dating simulation game released by Enix in 1985. Considered somewhat revolutionary for its time, this game helped lay the foundations for the dating sim genre.

Point-and-click / Simulator / Adventure / Comedy / Romance
The game begins with your character, whose family has just moved to the area, entering his new school for the first time. After class, you accidentally run into a conservative-looking girl wearing glasses. She introduces herself as Mizuho, but you can't help but notice her striking resemblance to your dream pop idol, Miho Nakayama. You pick up a good-luck charm Mizuho dropped to give back to her, then make a startling revelation - your photographer brother took a picture of Miho carrying the exact same charm! You go to the music room to confront her with this evidence - and this is where the true challenge of the game begins.

Simulator / Adventure / Visual Novel / Drama / Romance
Memories Off is a visual novel. Most of the game consists of text superimposed on still anime-style visuals. The interaction is restricted to occasional choices the player must make when prompted by the story development. Depending on these decisions the plot may advance into any of the six distinct branches, leading to different endings.

Point-and-click / Simulator / Adventure / Comedy / Drama
Doukyuu-sei is a 1992 erotic dating sim (the first of its kind) where the player can meet 14 girls to have a romantic relationship with. The player takes the role of a high-school student (default name Takurou) in a Japanese town; his parents have just moved into a large mansion in a good district. The boy has to go to the new school, but his mind is preoccupied with one subject only: pretty girls. Instead of studying hard, Takurou decides to explore the city and to find out more about its female inhabitants.

Simulator / Sport / Adventure / Erotic
Released in June 1985, Tenshitachi no Gogo (Afternoon of Angels) this was one of the first adult dating sims, an adventure game set in a Japanese high school. The goal is to seduce the star girl of the tennis club, Yumiko Shiraishi. To do this, the player needs to go around talking with her friends and possibly getting intimate with them as well.

Point-and-click / Role-playing (RPG) / Adventure / Action / Horror
Persona 3 Portable is an enhanced remake of Persona 3 for the PlayStation Portable. The game features an option to play as a female character, which alters some aspects of the story. In addition to the new playable character, there are two new difficulty levels to select from alongside the original game's three. The game also features some other story related changes regardless of the player character gender. The battle system is also updated to be closer that of Persona 4.

Point-and-click / Simulator / Strategy / Comedy / Drama
Kakyuusei is a 1996 PC-98 adventure dating sim where the protagonist must date (obviously) a girl or two or a dozen. It was ported to many platforms and has never been localized into any other language besides Japanese officially (only fan translations into Korean and Simplified Chinese). It’s a spin-off of the Doukyuusei titles also made by ELF.

Simulator / Adventure / Visual Novel / Romance
Marmalade Boy is an otome game, developed by Kuusou Kagaku and published by Bandai, which was released in Japan in 1995. It is based off the anime Marmalade Boy.

Simulator / Adventure / Visual Novel / Fantasy / Romance
Evergreen Avenue is a Visual Novel released on PlayStation in 2001. Choosing either a male (Catan) or female (Ira) character, you must help each of the seven spirits learn the ways of human life by scheduling sessions with them each week and playing mini-games to determine your effectiveness. Events will pop up from time to time, where you have personal conversations with the various spirits or with your rival. At the end of each month, you are graded in comparison with your rival, and you must sufficiently educate the spirits by the time six months have passed.