I’ve been thinking a lot about the movie The Princess Bride. Which, really, has been sort of a semi-consistent thing since childhood. Lately, though, something has occurred to me, and really, I don’t know why I didn’t think about this before. It’s about Westley. Namely, it’s the Dread Pirate Roberts problem.

Now, farm boy Westley is great—don’t get me wrong, but he’s a bit doormat-ish: sweet and kind, but lacking a little…something. Even as a child I though Buttercup was kind of a brat in the beginning and I wanted Westley to stick up for himself a little. So Farm Boy Westley wasn’t my thing. However, later in the film when he shows back up dressed all in black, expertly wielding a sword and full of swagger? We as the audience can’t help but love him.

I have no problem with this, even though it recently finally filtered in that Westley has spent his time doing some less than stellar things. He’s spent five years being the Dread Pirate Roberts…and as we’ve been told, the Dread Pirate Roberts leaves no survivors. In the five years that Westley has been gone, nothing has changed in the reputation of the Dread Pirate Roberts, and that means he’s still known as a murdering, pillaging, scourge of the seas.

Which is a little troubling. Now we all know that the rumor mill is easily manipulated, but even if this were the case and Westley wasn’t murdering every single person on the ships they raided, he’s still raiding ships. Basically, Westley has spent the last five years stealing, destroying and most likely killing (“Murdered by pirates is good.”) and we love him for it. Fezzik even tells us that “people in masks can’t be trusted” and yet we don’t listen. As an audience we have no problem reconciling this information with the character that we’re presented with in the beginning. Westley is still a good guy. He’s still the hero. We know this. We root for him. Why?

It’s because he fights evil. Wesley may do bad things and even if you don’t see his eventual goal of getting his true love as a “good,” by the end of the movie he’s at least done plenty for the side of right by thwarting the prince who was a skeezy, lying, torturing jerk—and who was trying to start a war which would have left countless dead.

All of this got me thinking about this kind of character—the kind that does awful things but we still believe is a good person. Look through your library and you’re bound to find a few like this. Robin Hood. Batman. Dr. Peter Venkman. (In the beginning of Ghostbusters he’s shocking a student even when he’s answering questions correctly just so he can hit on a pretty female student.) I mean, I loved the movie Red and what’s it full of? Assassins. Trained killers. But they’re good assassins.

I’ve been encountering a lot of these kinds of characters in Young Adult recently. They’ve been there all along, but I’ve been paying more attention to them, probably because my latest books have featured a bunch of teenage assassins. Though we can whole-heartedly accept these kinds of characters when we’re adults, we get a little squeamish about them when they show up in books and movies for younger audiences. Which is a little silly. Teen readers love these characters for the same reason we do—because as much as we love the good guy, the Superman who can do no evil, sometimes it’s hard to reconcile that kind of character with what we see in our daily life. We rarely come across someone who is 100% good. People are a mix of good, bad, and in between. Why wouldn’t we want to read about characters that represent our reality?

It makes sense to me that YA books especially would start to gravitate toward this idea. That’s the age where things shift from black and white ideals to various shades of gray. For most of us, ideals die as we age, killed off by life experience and cold practicality. It can be jarring and upsetting when that happens. It is only natural that readers would want to know that they’re not alone in this and to explore it in fiction where there are no repercussions. Where it’s safe.

I know when adult readers encounter darker and complicated plot lines and characters in YA, they can get upset. They don’t want teens to be ready for this stuff and they want to shield them for as long as they can from the murky complications of the outside world. When I hear this, though, I always wonder, do these people not remember high school? Or did they just not go to one like mine? Like it or not, even if your kids aren’t going through things themselves, their friends are. And most likely they are going to see their friends who are good do some bad things or make some poor choices. That’s how we learn and grow. So why wouldn’t we seek out fiction that represents what we see? Except, you know, maybe with pirates and magic and teen assassins, and vampires and werewolves and everything else that is weird and wonderful?

We can still love and appreciate farm boys who become murdering pirates, because sometimes life doesn’t give you good choices and you have to make the best of it. And, let’s face it, some people just look better in all black.

Lish McBride is an author, bookseller, and all-around ne’er-do-well living in the Seattle area along with her long-suffering Man Friend, her son, and her furry legion, which number many. (Well, three.) When she isn’t working, which is most of the time, and reading, which is the rest of the time, you can probably find her whining on Twitter about how she needs a nap. The first two volumes of her Necromancer series are available now as an ebook omnibus from Henry Holt.