The Gunslinger.

Saddle up.

Let’s start with Susan Delgado. She is canonically Roland's first love and girlfriend. And you can argue that Roland is straight because he liked a woman…but then I present you: Cuthbert Allgood, Roland's best friend.

But hey! You say, Cuthbert is only a friend. There are no hints in canon of anything romantic between them, or an attraction from Roland's part.

And then I'd tell you: you're wrong.

So, let's talk about Roland's loves.

Is no coincidence Eddie and Susannah end up in Roland’s ka-tet, since we all know ka is a wheel. We even get a canon confirmation that Eddie is Cuthbert’s twinner. It’s also no coincidence that Susannah chose to have that name, so close to Roland’s first love, Susan.

What I’m trying to say is these characters are supposed to mean something to Roland, so they are the people he loved the most: Cuthbert and Susan. These two meant the world to him and both their deaths dramatically changed Roland, once as a child and then as a adult.

In The Drawing of the Three, this happens:

When Roland thinks about loving, he names three people:

1. Allie. The woman Roland slept with in the first book, that got killed by the Man in Black.

2. "The girl in the window" that we later find out is Susan, Roland's very first love.

3. …and then Cuthbert. Roland's best friend since childhood.

So he names two love interests and then Cuthbert.

You could argue this was an idea of love in general…but if it was, shouldn't Roland name someone else like Alain or his mother? I think his mother should be more important than Allie, a woman he spent some time with before she died.

So that leads me to believe the people he listed here are all his romantic loves he had in his life.

And if you have any doubt that Susan and Cuthbert are equally important in Roland's mind, might I point out an interesting fact: Susan and Cuthbert get at least mentioned once (sometimes more) in every book, even in Wind though the Keyhole and The Little Sisters of Elyria.

I believe his friendship with Cuthbert ran a little deeper. Roland and Cuthbert were friends, but it is obvious his death affected him as much as Susan's. Sometimes their interactions feel romantic in nature. This is difficult to prove, since The Dark Tower is about platonic and family love, and the characters can be very expressive, devoted and even affectionate. Nevertheless, I wouldn't ignore:

- Roland reaching out for Cuthbert's hand.

- Cuthbert kissing Roland after they confronted each other.

- The whole Cuthbert being jealous and disapproving of Roland and Susan's relationship.

- The comics.

Aside from that, there are also some interesting moments about Roland and sexuality:

- When Callahan reveals he was in love with a man, Roland is the least surprised and scandalized of the entire Ka-tet. And he belongs in a Western/Arthurian mash-up universe.

- Also you can't forget to mention that the man Callahan falls in love with is named Lupe Delgado. Delgado. Like Susan Delgado, Roland's first love. If this isn't a hint to bisexual Roland, I don't know what is.

- When Roland meets King, for a reason that I don't remember, Roland asks Stepehn King if he likes men (yes, in a gay way).