go through? I will supply you with some character information and some context for my specific project, though I'm thinking

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?

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@Jessie137

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.

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: How do I figure out what "challenges/issues" my character could encounter/go through? I will supply you with some character information and some context for my specific project, though I'm thinking

More posts by @Gail2416123

: How to write from a rich "bad boy's" perspective? I am currently writing a story that alternates perspectives between the hero and heroine every other chapter. I have gotten a lot of work done

: Chapters - Writing Order I, like most writers, have a number of ideas about my current work in progress. I know how some chapters in the story will play out almost precisely (the ending

: ISBN and international translations for sale in another country If I understand the ISBN correctly, if I as a publisher, created a Spanish translation here in the US, but was also selling it

: Creating clues for a mystery subplot I am working on a story in which the characters must solve a mystery. It's a "team-building exercise" at school, in which they must work together. They

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