You're halfway through a novel and you catch yourself doing something uncomfortable—rooting for the villain. Or maybe you've just finished a book where nobody got what they deserved, and instead of closure, you're left with this strange, unsettled feeling. Was I supposed to like that character? you wonder. Should I feel bad that I did?
Here's a liberating truth: the best stories often don't want you to pick a side. They want you to sit in the discomfort of competing sympathies, to feel the pull of contradictory moral claims. Learning to appreciate this messiness doesn't make you a wishy-washy reader—it makes you a sophisticated one. Let's talk about how to stop looking for heroes and start finding something more interesting.
Gray Appreciation: Finding Satisfaction in the Unresolved
We're trained from childhood to expect moral clarity. Fairy tales have wicked witches and noble princes. Action movies have bad guys who practically wear signs. So when a novel presents us with a situation where everyone has a point—where the antagonist's grievances are legitimate and the protagonist's methods are questionable—our brains short-circuit a little. We want someone to root for. We want resolution.
But consider what happens when you let go of that need. Suddenly, a story like Wuthering Heights isn't a frustrating tale of awful people being awful—it becomes a meditation on how love and cruelty intertwine, how trauma perpetuates itself across generations. Heathcliff isn't a villain to condemn or a romantic hero to swoon over. He's both, and neither, and that's precisely why readers have argued about him for nearly two centuries.
The satisfaction in morally gray fiction comes from a different place than the satisfaction of seeing justice served. It's the pleasure of recognition—of seeing the messy, contradictory nature of real human motivation reflected honestly on the page. When you stop waiting for the story to tell you who's right, you start noticing how carefully the author has balanced competing claims to your sympathy. That craft becomes its own reward.
TakeawayWhen you catch yourself frustrated that a book won't declare a winner, pause and ask: what would be lost if it did? The unresolved tension is often where the real meaning lives.
Perspective Gymnastics: Holding Multiple Sympathies at Once
Here's a reading exercise that will change how you experience complex fiction: every time you feel your sympathy shifting, don't let go of where it was before. A character reveals something ugly about themselves? Fine—but keep holding your earlier compassion alongside your new disappointment. Think of it like juggling emotional responses rather than trading one for another.
This is what separates a casual reader from an engaged one when tackling something like Gone Girl. Both Nick and Amy do terrible things. A surface reading bounces between them—sympathizing with whoever seems least awful at any given moment. But a richer reading holds sympathy for both simultaneously, understanding how each became capable of their particular cruelties. You can feel for Amy's genuine grievances about marriage and gender expectations while being horrified by her actions. These responses don't cancel each other out.
The trick is to stop thinking of sympathy as a limited resource. You don't have a fixed amount to distribute. You can feel for the murderer and the victim, the betrayer and the betrayed. In fact, the most devastating moral fiction often depends on this—it needs you to care about everyone involved to feel the full weight of the tragedy. When you master this juggling act, you'll find that morally complex books stop feeling confusing and start feeling unbearably alive.
TakeawayPractice holding contradictory sympathies like you're collecting them rather than choosing between them. The goal isn't to pick a side—it's to feel the full weight of the conflict.
Judgment Suspension: Why Waiting Enriches Everything
Your book club is discussing a morally murky novel and someone asks the inevitable question: But do you think what she did was right? And there's pressure to answer, to plant your flag. Here's your permission slip to resist: the most interesting response is often I'm still thinking about it. Not because you're wishy-washy, but because you're doing the harder, more rewarding work.
Postponing moral judgment isn't the same as having no moral compass. It's recognizing that fiction often asks questions rather than providing answers, and that rushing to verdict means missing the question entirely. When you read Lolita and immediately declare Humbert Humbert a monster (which, obviously, he is), you might miss Nabokov's more uncomfortable exploration of how seductive his language is, how easy it is to be charmed by eloquent evil. The book is about that seduction. Refusing to feel it means refusing the book's real challenge.
Try this: the next time you finish a morally complex novel, give yourself a waiting period before deciding what you think. Sleep on it. Let the characters' voices argue in your head. You'll often find that your first-instinct judgment gets more nuanced—not softer, necessarily, but more informed. The best moral fiction earns its complexity, and it deserves readers willing to sit with that complexity rather than flatten it into easy conclusions.
TakeawayWhen someone asks what you think about a morally ambiguous character, 'I'm still wrestling with it' isn't a cop-out—it's often the most honest and engaged response possible.
The next time you pick up a book full of morally questionable characters doing questionable things, try approaching it as an invitation rather than a test. The author isn't asking you to approve or condemn—they're asking you to understand, which is much harder and much more rewarding.
Let yourself be pulled in contradictory directions. Let the uncomfortable questions stay uncomfortable. That's not a failure of reading comprehension—it's the whole point. The messiest books often leave us with the cleanest insights into what it actually means to be human.