Thorin:

"No more living in those shadows. You and me, we know how that goes."

 - Thorin to the Company after reclaiming Erebor, his eyes shining with a peculiar light

(Come Alive; The Greatest Showman)

Fili:

"He said there's nothing like your smile, sort of subtle, and perfect, and real. And he said you never knew how wonderful that smile could make someone feel."

- Kili to you about what Fili has said to him about you

(If I Could Tell Her; Dear Evan Hansen)

Kili:

"Is there some lesson to learn? Should I never have wanted? I never even got started... Or were the decks always just this stacked?"

- You, in vain at the sky, overwhelmed by all the things happening in your life now

(Black Friday; Black Friday)

Bilbo:

"How can anyone sleep? There was never such a night before! I feel like putting my arms 'round my knees, and squeezing tight as possible, and flying away..."

- You to Bilbo, feeling like you'll never really think of Erebor as home

(No One Else; Natasha, Pierre, and the Great Comet of 1812)

Legolas:

"Flowers, I remember fields of flowers, soft beneath my heels. Walking in the sun, I remember someone, someone by my side, turned his face to mine... And then I turned away, into the shade."

- You to your brother, Frodo, about you oddly finding it hard to remember Legolas

(Flowers; Hadestown)

Thranduil:

"I've heard it said that people come into our lives for a reason, bringing something we must learn, and we are led to those who help us most to grow, if we let them and we help them in return. Well, I don't know if I believe that's true, but I know I'm who I am today because I knew you."

- You to Thranduil in a moment of sentimentality

(For Good; Wicked)

Lindir:

"Now, shoulders back and stand up tall, and do not walk, but try to float."

"Am I floating?"

"Like a sinking boat!"

- You as a child learning all the ladylike ways of an elven princess, spoken between your tutor, then you, then a giggling Arwen

(Learn To Do It; Anastasia)

Elrond:

"Remember: you're never fully dressed- though you may wear the best -you're never fully dressed without a smile." 

- You to Elrond, straightening his robes before attending an important dinner, reminding him to smile

(You're Never Fully Dressed Without A Smile; Annie)

Gimli:

"I apologize if it makes you feel bad, seeing me so tense, no self-confidence." 

- You to Gimli after the battle of Helm's Deep

(Winner Takes It All; Mamma Mia!)

Merry:

"Someday... life will be fairer. Need will be rarer. Greed will not pay."

- You, daydreaming aloud to Merry of a better future

(Someday; Hunchback of Notre Dame)

Pippin:

"I'll come running, to fight, and I'll be at your door when there's nothing worth running for."

- Pippin comforting you right before Nearing The Catalyst

(When Your Mind's Made Up; Once)

Sam:

"You* left, but I'm still standing, spinning, on this infinite road, terrified of letting you go. No light above, and there's no hope below, and I don't know which way's home."

- You to yourself after they leave you behind

(Home; Beetlejuice)

*'You' in this context is Sam

Frodo:

"Eilian."

"Rainbow."

"Amlug."

"Serpent."

"Minuial."

"Dawn."

"You're sure?"

"I'm sure."

"Three out of three, you did alright."

"Teach me a little more."

- You teaching Frodo a little Sindarin

(Sunrise; In the Heights)

Faramir:

"You will live! Théo, you're going to live. It's too soon, too soon to say goodbye."

"Yes, Éalryth, forbid me now to die. I'll obey... I will try..." 

- You to your cousin Théodred on his deathbed

(Epilogue/Finale; Les Miserables)

Boromir:

"New, and a bit... alarming. Who'd have ever thought that this could be? True, that he's no 'Prince Charming', but there's something in him that I simply didn't see..."

- Boromir; you musing to yourself after learning he brought you to Rivendell

(Something There; Beauty and the Beast)

Aragorn:

"I imagine death so much it feels more like a memory. When's it gonna get me? In my sleep? Seven feet ahead of me? If I see it coming, do I run, or do I let it be? Is it like a beat without a melody?"

- You to Aragorn in a rarer moment of dreary philosophy

(My Shot; Hamilton)

Bard:

"We wait to laugh. We wait to cry. We wait for every hopeful breath."

- You to Bard one night many months ago, expressing the feeling of stagnancy you just can't seem to shake off those past few weeks

(Waiting; The Addams Family)

Haldir:

"If I could just find the right words to say, would you stay here?"

-  You to yourself, wishing you could have gathered your feelings better in the barn

(Stay; Amélie)

Éomer:

"We're supposed to all be ladies, and be nurturing, and care. Is that really fair? Boys get to fight, we have to share." 

- Éowyn to you, expressing her dissatisfaction with the gender roles put upon her by her society, a frustration of which you totally agree with

(I'd Rather Be Me; Mean Girls)

Bofur:

"I could find the whole meaning of life in those sad eyes. They've seen things you never quite say, but I hear. Come out of hiding, I'm right here beside you, and I'll stay there as long as you'll let me, because you matter to me." 

- Bofur to you, holding you close after you wake from a terrible nightmare

(You Matter to Me; Waitress)

Up next: Prelude to Confessions

SONGS

Thorin:

https://youtu.be/BDd9dejw2HY

Fili:

https://youtu.be/B7h7c_L_Yp4

Kili:

https://youtu.be/LAZgYL0p2zk

Bilbo:

https://youtu.be/OL6GLr3k_Vo

Legolas:

https://youtu.be/EVy9WaTzTiA

Thranduil:

https://youtu.be/Y8YMfgu92hQ

Lindir:

https://youtu.be/fB2R5BNndy4

Elrond:

https://youtu.be/SVGNjWPGVbA

Gimli:

https://youtu.be/0d3wxfS4Dtw

Merry:

https://youtu.be/r0ExGPIpO6k

Pippin:

https://youtu.be/Qt1doLkw64w

Sam:

https://youtu.be/6Xt3WNuB-oc

Frodo:

https://youtu.be/ieNK8PYoS4A

Faramir:

https://youtu.be/Rq89hmbAHv0

Boromir:

https://youtu.be/9VMOPpHzbCQ

Aragorn:

https://youtu.be/Ic7NqP_YGlg

Bard:

https://youtu.be/Yaf8jDKtvcU

Haldir:

https://youtu.be/ZlvLU78jTwI

Éomer:

https://youtu.be/u075TmA_6TU

Bofur:

https://youtu.be/AREDtpRZTSA

Up next: Prelude to Confessions