The player needs to keep his relationship up with all the potential suitors.
If one falls too low, then the suitor gains a "bomb." When the suitor has a bomb, then she'll gossip about the player to the other characters, lowering his relationship with them.
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Modern games have optional "social link" features, where you can build up relationships between supporting characters granting different benefits.
These are often found in Tactical RPG games, where unlocking a social link can boost certain stats.
Because of the fact that they're relatively easy to make, dating sims have been created by many indie designers.
Visual novel creation platforms such as Ren'Py and Novelty exist and are designed for people with minimal experience coding.
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).