In Defense of Morally Questionable Fictional Men

I have a confession to make.

Some of my favorite fictional men would be absolutely insufferable in real life.

Possessive? Yes. Obsessive? Occasionally. Morally questionable? Almost exclusively. A concerning relationship with violence, authority, or the general concept of personal boundaries? Apparently, that’s where things start getting interesting.

And before anyone feels the need to intervene, I am perfectly capable of recognizing a red flag.

I just happen to find them considerably more entertaining when they’re attached to a fictional man.

I’ve always been fascinated by characters who exist somewhere in the gray areas of morality. The ones who are capable of terrible things but also demonstrate extraordinary loyalty, tenderness, or devotion under the right circumstances. There’s something compelling about a character who is frightening to almost everyone except the person they’ve chosen to love.

Not necessarily healthy, of course.

But compelling.

And I think that’s an important distinction.

Enjoying something in fiction doesn’t mean wanting to experience it in real life.

I can appreciate a fictional man who threatens to destroy an entire kingdom for the woman he loves without wanting someone to commit actual crimes on my behalf. I can enjoy an obsessive supernatural entity without considering surveillance an acceptable form of courtship.

Fiction gives us the opportunity to explore relationships, behaviors, and moral dilemmas without having to endorse them.

And frankly, that freedom is part of what makes storytelling so much fun.

In The Shadow, the Hat Man is not exactly a shining example of emotionally healthy romantic behavior.

He’s possessive, obsessive, occasionally jealous, and has spent decades watching a woman sleep.

I recognize how that sounds.

I wrote the book.

But what interested me about his character wasn’t simply making a monster romantic. It was exploring the contradictions that make him both frightening and strangely appealing. His capacity for violence exists alongside his devotion to Ella. His understanding of love isn’t particularly human, and neither are his ideas about boundaries.

He’s not meant to be a model boyfriend.

He’s a supernatural entity whose idea of protecting someone is considerably more extreme than anything a licensed therapist would recommend.

And that’s precisely what makes writing him entertaining.

I don’t particularly enjoy characters who are cruel simply for the sake of being cruel. What interests me is the complexity beneath the behavior. Their motivations, their contradictions, and the circumstances that make readers question why they’re sympathizing with someone they probably shouldn’t.

I want to understand what makes a monster capable of tenderness without pretending that tenderness somehow erases everything else.

And I want my readers to be able to enjoy those contradictions without feeling obligated to justify them.

Sometimes a character can be a terrible person and an excellent love interest.

Sometimes the red flags are an integral part of the plot.

And sometimes you just want to read about a morally questionable supernatural man who would burn the world down for one woman.

Would I recommend dating someone like the Hat Man? Absolutely not.

Would I write another book about someone equally concerning?

Without hesitation.

Because at the end of the day, I don’t write relationship advice.

I write fiction.

And apparently, my fictional men are going to continue being a collective disappointment to the mental health profession.