Indeed!
The speaker is Luthien, her double is Arwen. Proud is Thingol Greycloak / Greymantle, and Humble is Gandalf Greyhame / Greymantle / other forms of grey attire.
Did Gwaihir appear in the First Age?
I thought Thorondor took all the lead roles there.
Anyways, the riddle was solved very much by a group effort, Urwen identifying the female half and Huey the male half of the characters. Huey had the final explanation, but of course it wouldn't have been possible without Urwen's contributions. I think officially it goes to Huey but I wanna give Urwen a big kudos for cracking the first half!