An Insanely Detailed Ask Meme Brought to You by Tolkien's Characters

Frodo: What is your deepest wound, and do you still hurt from it?
Bilbo: When did taking a chance improve your life?
Samwise: Have you ever done something for a friend that you would never have done on your own?
Merry: Who would you swear loyalty to, or to whom have you already done so?
Pippin: Tell me about when you did something that no one thought you could do.
Aragorn: What is your heritage? Do you embrace or reject it?
Boromir: Did your father leave an impact on your life?
Gimli: Have you ever had an opinion about someone that turned out to be completely wrong?
Legolas: What has been your most unlikely friendship, and did it last?
Gandalf: Has your public appearance and ever changed radically?
Elrond: Do you have overprotective relatives, or do you fill that role?
Arwen: Did you ever make a decision your family didn't agree with?
Elladan: Have you ever failed to help someone you cared about?
Elrohir: Do you have siblings?
Galadriel: Would you consider yourself wise?
Celeborn: Are you content with being the less-popular one in a relationship?
Celebrían: Have you ever done something that took a turn for the worse that you weren't prepared for?
Haldir: Has your popularity ever changed unexpectedly because of something minor?
Éomer: What are the things you consider to be worth fighting the system for?
Éowyn: Have you ever overcome prejudice in a significant way?
Théoden: When have you been wrong but refused to see it?
Gríma Wormtongue: Do you sometimes make bad choices for selfish reasons?
Saruman: Do you want power?
Sauron: What is your greatest weakness?
Melkor: Has greed or the desire for material goods ever backfired on you?
Ungoliant: Are you proud of your children or younger relatives?
Shelob: Are you afraid of the dark?
Finwë: Do you come from a prestigious family line?
Fëanor: Does desire tend to blind you to the consequences of your actions?
Nerdanel: Have you ever ended a relationship because your partner was doing something you didn't agree with and you couldn't stop them?
Maedhros: What is the greatest thing you have ever lost?
Maglor: Do you believe in redemption?
Celegorm: Have you ever had a pet that impacted your life greatly?
Caranthir: Do you have a temper, and has it ever gotten you into trouble?
Curufin: What have you inherited from your family lineage?
Amrod: Do you have a friend or sibling that you have a special bond with?
Amras: Has your family ever done something that ended up hurting you?
Beren: Will you do anything for love?
Lúthien: Do societal norms exist to be broken?
Thingol: If you believe in luck, do you think you've had good or bad?
Melian: Have you ever had a significant other that was of a lower social class than you?
Eöl: Did you ever have a goth phase?
Aredhel: Is listening to other people something that is important to you?
Glorfindel: Have you ever taken on a challenge others have deemed impossible and won?
Thror: Do you value wealth?
Thráin: Do you consider yourself a selfish person?
Thorin: What have you lost that you wish to regain?
Balin: Are you older or younger than most of your friends?
Dwalin: Do you have any hobbies?
Fili: Do you have a good smile?
Kili: Have you ever suddenly been considered attractive where before you were just sort of there?
Dori: Are you a musician?
Nori: Is it common for you to notice things others have forgotten or missed?
Ori: Do you write or speak multiple languages fluently?
Óin: Would you consider yourself a superstitious person?
Glóin: Are you skilled at something most would consider unusual or esoteric nowadays?
Bifur: What is your most interesting injury, and how did it happen?
Bofur: Do you consider yourself an optimist or a pessimist?
Bombur: What is your relationship with food?