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Source: https://writers.stackexchange.com/q/26559
License name: CC BY-SA 3.0
License URL: https://creativecommons.org/licenses/by-sa/3.0/

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?**

Original score: 2