Hmm, Gwindor may have my vote now :'( He's kind of the Elven equivalent of *I forget the name...the lame woodman who loves Nienor* :'(
I think any Elf who got close to a mortal would be sad though...especially those who knew many...imagine meeting a race. They only live for 1 year. So you get close tothem. They die, You get close to their kids. They die. And this goes on for generations, so by the time you, the human, die,let's say at 80, you will have experienced the deaths of countless close friends.
:'(