While the genre started in the 1980s, arguably the first dating sim to make it big is Tokimeki Memorial, first released for the PC in 1994. Due to its popularity, the game been remade multiple times (Tokimeki Memorial: Forever With You, Tokimeki Memorial: Densetsu no Ki no Shita de, etc.) and has been ported to multiple systems (Game Boy Color, Play Station, Super Famicom, mobile phones, PSP).
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Just like how there are multiple suitors, each suitor has multiple endings.
The endings typically come in two types: good ending and bad ending.
The adult games page is easily more popular, with some games reaching views in the millions.
With titles such as "Aching Dreams2 Hentai Game," "Meet'N'Fuck Road Trip," and "Orgasm Girl," it's pretty obvious what sort of direction these games are heading into.
Good interactions boost your meter, bad interactions reduce it.
In order to woo a suitor and get the "good ending," the player needs to pick the best choice out of multiple options (usually two to three) that reflects the suitor's personality.
Other options are flash games, which are less focused on characterization and are hosted on websites such as Newgrounds.
Newgrounds has two main dating sim pages: an all ages one and a page for adult games, found under the "Adult Features" collection instead of the "Games" tab.
The cheap price of the game helped spread it to the popular consciousness.