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Different skills will lead to different situations.
In recent years, there have been many Role Playing Games that incorporate dating sim elements.
These dating sim elements are often referred to as Romance Sidequests in the RPG genre.
In these simulation dating games, you date different girls and try to win their hearts.
Usually, you will need to get some sort of job, earn money and buy expensive gifts.
In many games, you will need to improve your skills too, like Charisma, Intelligence or Strength.