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I will supply you with some character information and some context for my specific project, though I'm thinking my question could be relevant for almost any story.

I am writing a story involving with a "bad boy" main character "X" (hero) and a female character "Y" (to-be heroine). I have a clear idea of the hero and his place in society: Very wealthy for his age (inherited fathers company). Perceived as somewhat of a womanizer, In my opinion he's misunderstood. I plan for the two characters to fall in love at a later point in the story. Before that however, I want the hero to go through some challenges/struggles before eventually ending up with the heroine.

As of now, there are some "romantic" issues: "X" has an affaire with B, B is separated from C, C is interested in "Y" and "Y" is also being charmed by ex-boyfriend E..

Aside from the romantic issues, I'm having trouble coming up with challenges/issues that make sense for the hero to go through/solve.

So; I am not looking for answers regarding my specific plot, but rather a broader answer to the question:

How do I figure out what challenges fit a character?

storbror
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T. Afrin
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2 Answers2

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As Anne Lamott would say, we all have our own "mental illnesses", and they usually stem from our experiences. If your hero is a "bad boy" who inherited a bunch of money, has a company, and who seems to have a thing for the secretary, consider how these aspects of his life came to be: If he inherited money from his father, would that affect him positively or negatively? Would he invest carefully, or blow it all on his wants rather than his needs? Would he take responsibility, or dodge it and thus incur the wrath of others?

Going further into his past, you can consider how his childhood caused certain "bad boy" problems in his adult life. If his dad was off making money, did he have time for his son? Did the son (ie. your hero) begin to act out to get Dad's attention? Did that carry over into his adult life? I find that character's internal issues usually create external problems for them. If you let your bad boy hero act the fool, he might get into trouble with someone else and, by consequence, help the story progress.

Brittany Wright
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The basic shape of any character's story arc is that they want something and there are forces that make it difficult for them to get it. They try the least expensive thing they can to achieve their desire, and are rebuffed. They then try the next least expensive thing and are rebuffed again. This repeats until we get to the climax where we discover just how much they are willing to give -- how much they are willing to bleed -- to achieve their desire.

The issues that a character goes through are therefore driven by their desire. They are all about their attempt to get what they want and the things that prevent them from getting it. So the first question you have to ask yourself is, what does my character want? What is the desire that drives him towards the climax of this story?