Probably a warning is in order. There's a mystery in our fandom. The fans consider Vincent the most desirable lover, man, friend, son, etc. But, at the same time, a very popular way of depicting him in fanfic and discussions is as a weak, irresolute, stubborn, whining, frustrating individual, with huge self-esteem issues, depending on Father and Catherine for most of the decisions –- or non-decisions -– of his life, continually on the verge of "I want, but I can’t," passively and cowardly waiting for someone to shake him and persuade him to wake up. Now, of course we're talking  of dreams, which are the children of an idle brain, as Father would quote, and every brain can dream a different dream, but in the very personal thoughts that follow, there are no traces of that boring (for me) person and of that inconsistent and irritating (for me) approach, as I can't find any traces of this in the episodes, where my idle brain sees something quite different.

O ne night, several months after the brutal attack that almost killed her, Catherine Chandler finds a book on the floor of her balcony. She lifts her eyes; Vincent is there, in the shadows. It had not been a dream, he was real.

Vincent is the magical element of a story that might very well be a "real", contemporary story. We know that the tunnels are there, under New York City; we know that outcast societies do exist; we know that incidents and miracles like Catherine’s do happen; but Vincent... Vincent is something else.

Let’s forget for a moment the symbolic meaning that is the very heart of our story, the dualism of Above/Below, of Light/Shadow, of Inside/Outside, where the sharp confines of the fairy tale roles blur, and we soon enough understand that it’s difficult to tell who is the Beauty and who is the Beast, and in this telling mirror we recognize ourselves. No, let’s just talk of Vincent, the creature, according to Catherine, who is "also the best part of what it means to be human." (Nor Iron Bars a Cage)

In that same scene of NIBAC, Catherine continues, "if you take away his freedom, then you take away that very part that makes him most human!" In the scene before, it’s Vincent himself who replies to professor Hughes, the poor prisoner of a bitterness which had killed his soul and his career, when asked, "Vincent, what are you?" "I am only what I am. If you cut me, I will bleed. If you strike me, I will strike back. And if you keep me in chains… I will die." Poor Hughes does not realize that the "animal" he wants to study is subtly quoting Shakespeare to him, but we recognize that Catherine’s intuition is true: Vincent, to be alive, needs to be free.

This is the powerful struggle which Vincent, "the conqueror" according to the meaning of his name, has fought all his life. Always, since the full moon night when the little girl cried at seeing the child Vincent, and made him tell "Devin and Father and everyone that would listen that I would never go back again," he stubbornly chose the moon, to live and to bleed, not the darkness, to hide and be safe.
Charles: But you went back.
Vincent: A month later. Devin made me. He promised to stay close and he reminded me that the moon would be full again. (Brothers)

By fighting that powerful struggle, against his many, terrible limits, he chose to be human -- the best part of what it means to be human.

There is indeed a prisoner in the tunnels, and that prisoner is Father. He is prisoner of his bitterness, of his fear, of his self-pity, of his cowardice. Not so different from Hughes. Of course this does not mean that he is a mean individual. Along with these dark sides of his character, we all know also his generosity and open heart, his vision and wisdom. Only, he is a prisoner, he can’t fly. He set boundaries for himself, did wonders within them, and declared that beyond those boundaries there was nothing good. He tried to teach this same narrow mindedness, this same fear and bitterness to Vincent, but he failed, because Vincent’s heart wants to fly. It allowed him to be nurtured by Father’s best qualities, rejecting what would limit it. There are a number of occasions when Father tries to "keep Vincent in chains," with words, with arguments, but we see as many times Vincent simply ignoring or plainly disobeying him. I can’t remember any time that Father managed to restrain him, except in that dream which is Remember Love: a nightmare, in fact. "Vincent, don’t tell her anything!"... and in the next scene, we hear Vincent telling Catherine everything about the tunnel world. And he had already disobeyed by bringing her Below in the first place. "Vincent breaks their stupid rules too," says Mouse in Shades of Gray. From the "She can only bring you unhappiness!" -- "Then I’ll be unhappy!", of the Pilot, to the beautiful "Even love can wound, Father. The grave is a fine, safe place, but if we live, we bleed" of A Kingdom By The Sea, throughout the episodes we see Father trying to restrain Vincent and kill his "great expectations", in vain. Vincent wants to fly. And so, we can have that beautiful scene, in Temptation:
Father: You know, you two share something quite extraordinary… Something that touches the best in all of us.
Vincent: To hear those words coming from you, it must.
Father: You mean, there's still hope, even for an old man like me?
Vincent: Always.
Vincent, the conqueror, conquers the prisoner’s heart.

Vincent needs to be free, and he needs to hope, "always." He needs this to be human. We all do, but of course, Vincent more than anyone else. That’s why, I think, he falls in love with Catherine. Catherine is everything he is not; she is on the opposite side of the spectrum, as far away from what is possible for him as is conceivable. Loving her is foolishness, and he hopelessly falls for her. I won't talk of Catherine here, maybe another time. I’m considering Vincent, for whom the tunnels are not room enough. He scouts the night, he explores and needs to be Above as much as he can, in the Park, in the alleys, on the rooftops. I think that Vincent never fell for a woman of the tunnels, apart from the natural and tragic teenaged attraction to Lisa -- and also Lisa is a flying butterfly, not the typical tunnel girl (Arabesque). Even after that, probably it might have been possible for him to have a "normal" tunnel life, with somebody who knew him very well, grew up with him and accepted him. But he needs the moon, not the candlelight. So, he falls for Catherine, the impossible dream. She opens for him a whole world of possibilities, and he recognizes in them what he is longing for, his "great expectations". Beauty, freedom, opportunities to interact with that forbidden world from a completely new perspective... A soul as thirsty for meaning and purpose, for hope and dreams as his own, despising the boundaries. When the bond ties him to her feelings surging from all of this, he is captured forever. And he does not retreat to whine and long. Maybe he struggles to fight his impossible dream, but eventually, again, his heart accepts the risk of being hurt -- "Then I’ll be unhappy!" -- and he goes to her. That intact beautiful face is a shock; he starts to believe that his high hopes are crazy after all... but Catherine had done her homework, and she takes over from that point, not letting him go.

Another feature of Vincent that also makes him the best part of what means to be human is his compassion. A compassion that colors his self perception and his approach to others. A miraculous approach. As Father says to Margaret about him, in Song of Orpheus, "I came to know someone who had every reason to curse fate and feel punished, and yet he accepted all that life had to offer with gratitude and love." Instead of feeling punished, instead of cursing fate, Vincent turned his pain into a compassionate outlook on others, so deep that he can see and recognize the fear of being alone and rejected that disfigures their hearts, if not their faces.
Vincent: Charles is not a problem, Father. He is a human being… in pain.
Father: Believe me, Vincent, I do understand his pain.
Vincent: Do you?… Can you?… I can. (Brothers)

Vincent: I know what I am. Your world is filled with frightened people. And I remind them of what they’re most afraid of…
Catherine: Their own ignorance…
Vincent: …Their aloneness. (Pilot)

Vincent: When I walk the city streets, I wear a cloak with a hood to shadow my face.
Charles: But your face is--
Vincent: A mirror, like yours. Where frightened men see the shape of their own fears, and small men see only ugliness. (Brothers)

No, there is no ugliness in Vincent’s face and soul. He is fully aware of it. It’s not his looks that scare him. In the episodes we see several times that Vincent looks at himself, never with shame or repulsion: in the mirror (When the Blue Bird sings), in Elizabeth’s picture (Ozymandias), in the water of Narcissa’s basin, in Kristopher’s painting, when we see him even a little smug. And the care he puts into his clothing is telling too. No, it’s not his looks that frighten him. Nor the Beast. The Beast has useful powers, and he does use them. Mitch’s terror in Beast Within, as well as the efficient way he dispatches those men, speak about the "jungle law" he accused Vincent of earlier  in the episode. And in China Moon, in The Alchemist, in The Outsiders, when their tunnel world is menaced, we see Vincent proud to be the protector.

Vincent: All men are demons when their homes and loved ones are at risk. (China Moon)

Father: A violent confrontation with these people must be avoided.
Vincent: And when violence can no longer be avoided?
Father: Only then. When there is no other option.
Vincent: And when that time comes Father, you must not hesitate.
Father: Of course, I won’t hesitate.
Vincent: You will let me go out, to do what must be done - whatever must be done?
Father: I pray that won't be necessary.
Vincent: So do I.
Father: That is not who you are, to us.
Vincent: That is who I am... perhaps even my fate. The very part of me that I struggle to overcome gives me the power to protect the people who protect me - who give me life.
Father: Vincent, that is not your fate.
Vincent: My survival depends on this world. There is no other choice for me. For me there is no other place, Father. (The Outsiders)

But.

But there is something that frightens him immensely. Not the Beast, but the blindness that its fury brings to his free choice. To his freedom. One of the times we see Vincent most ashamed and humiliated is not after some gory killings, but, without a drop of blood shed, after Catherine rescues him from the horrible madness of Paracelsus' drug, when he has "seen the demons Paracelsus has unleashed, felt them inside of me. How can I explain… become disconnected… as if the dark side of your imagination eclipses all compassion, all dignity…" and when he confesses, "How ashamed I am, that you saw me as I was." (The Alchemist)

Yes, ashamed. Vincent hates to be flawed. "You must not see me like this". It's evident in that extraordinary dialogue with Catherine in A Fair and Perfect Knight, when he confesses his jealousy.
Vincent: You must leave.
Catherine: No.
Vincent: Leave, now.
Catherine: Why do you want me to leave?
Vincent: Because what I'm feeling... My thoughts... Shame me.
Catherine: Tell me. Tell me what you feel!
Vincent: You must not see me like this.
Catherine: Please don't send me away!
Vincent: My thoughts are poisonous!
Catherine: Tell me these thoughts.
Vincent: What you shared... I envied.
Catherine: Vincent.
Vincent: I betrayed Michael. I betrayed you. Everything I hold dear.
Catherine: How did you betray us?
Vincent: I know what it is to love you... I love Michael like a brother, like a son. But his life has been such a struggle... He needed to be healed by your tenderness. And yet, I was unwilling to share your love with anyone.
Catherine: Don't be ashamed of those feelings.
Vincent: It violates everything I believe.

The research of this stiff perfection is his weakness. "Let me share your pain," Catherine asks at the end of Outsiders. "How can you even look at me?" is his reply. Vincent must learn to allow somebody to look at him and see his wounded heart, to share his pain, like he is willing to do for others, like he taught to do, especially to Catherine: "That's what you did for me" she says in Trial. Giving help and accepting help, is the tunnel golden rule. Even Vincent can’t be perfect, just because he’s human, the best part of what it means to be human. Like all of us, he needs to learn to be humble. And he does. The dark Outsiders is meant precisely to show this, and it has its true, beautiful ending in the beginning of the next episode, When The Blue Bird Sings, when the flawed knight, ashamed of having been seen in his furious misery ("Stay away!" he had ordered Catherine on her balcony), surrenders and accepts to be loved even if he is flawed, even if he feels unworthy, because there is no way to deserve love -- that would not be love, just a reward.

Vincent: Lancelot was fatally flawed. Destined never to find the grail.
Catherine: Still... he was the greatest knight of all.

And then the Blue Bird, and Vincent's heart, can fly.

S