Not him either.
*whsipers* It's a she.

Luthien?

Nope!

Arwen?

Still no

Galadriel, perhaps? She was certainly a long way from the land of her birth, and unable to return until she passed the test of the Ring.

Hurray, you've got it!
 

It's her indeed.

Thank you, Evisse. :)

Next up

Shelob to Frodo? :p

But of course! :D

Your turn to puzzle us Evisse.

Thanks. I'll do my best. :)

From song "Wolf and Raven' by Sonata Arctica.

Boromir perhaps? He's the most prominent repenter. Although Kill the King doesn't really seem to fit... :confused:

Nope, not Boromir. This one's even more fallen, and not as prominent a repenter.

Grima wormtoung ;)

Yep! :) Your turn.

breathe, thread!
 

How about:

(Nightwish, Wishmaster)

This could be applied to more than one, so if you explain your answer, you got it! :)

a guess... or two
 

Sauron's takeover as ultimate Baddie of ME from his old Master, Melkor?

or perhaps

Telchar the smith, outdoes his former master Gamil-Zirak when he forges the Dragon Helm, Angrist, and Narsil?

Maby Frodo? he followed people and tried to learn more about his quest (being an apprentice) then after the taming of Gollum he was 'master'

Sauron was my thought too. That and Feanor. Telchar is a good example too.
So, your go, Sophia!

Vinyacoriel, I'm afraid Frodo is a bit ambiguous...you could say he was an apprentice, but not in the true sense of the word, more like we're all apprentices, in that we learn from the wiser ones...

Any excuse to quote the Who...
 

From "Sea and Sand" by The Who

~Sophia

's been a long time
 

Didn't think this was so very difficult.

Think lovers... think ocean... think spoiled plans.

Maglor, perhaps?

Relating to Maglor and the silmarill. This may be obscure, but here is my reasoning.

Maglor was in love with the silmarill, as was Feanor, but had to part with it when he threw it into the ocean.

*Is hopeful*

Amroth and Nimrodel?

Sorry Hookbill, but I was going for Amroth and Nimrodel.

Your turn Nuranar. :)

This is harder than I thought...
 

"The Riddle," from The Scarlet Pimpernel

Easy? Ridiculous?

A classic guess by now:
 

Frodo to the Ring?

Nope.

Frodo to Gollum?

No again.

It's not an obvious one. I just hope it isn't too far out there...

Erendis to Aldarion?

No. Perhaps it's a wee bit more obvious that that one... ;)

A hint, please, Nuranar? ;)

Yikes, thanks for the nudge.

OK, it took me a while to to remember what it was! Hints: The events referred to happen in the First Age. And think of burning.

going with the obvious:
 

The burning of the ships at Alqualondë with Feanor speaking?

No, but keep trying!

It's been a while, so here's a new one!

Crazy Train, by Ozzy Osbourne

Well...the (maybe) obvious answer is Frodo... I'll go with that first.

That's the one I had in mind as well. Your turn. :)

Ok then...

Nightwish, Gethsemane.

This last bit here makes me think particularly of Elrond... is it him?