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Maybe you want to prove to the world that you can make a full-blown Dating Sim without problems like illogical choices (or gratuitous sex).
Or perhaps you want to mix some relationship elements into your mainstream video game. The first decision you make will unlock a major Event Flag for your story/game: If you're not creating a product with the intention of selling it, then know what you're getting into.
The second decision which will shape your game: Who is your main character, and what is their sexuality?
The following options will make a huge difference: Any of the above could conceivably be crossdressers.
Dating sims (or dating simulations) are a video game subgenre of simulation games, usually Japanese, with romantic elements.
You can create a love story in which a single sex scene is an important landmark for the characters.Or you can create a game filled with challenges and/or puzzles, and make it difficult to get to a sex scene.Just like in the Write a Magical Girlfriend Series entry, a male main character may be an Unlucky Everydude. Also, a main male character can sometimes be a Marty Stu who gets all the girls with no effort.Then set a realistic deadline for yourself, and don't change it.The English-speaking Ren Ai Game community has too many examples of games which only had demos, or which never amounted to more than ambitious plans.
Don't let all of them be happy, because if the main character is not allowed to fail, then your story/game may lose its emotional impact.