both! but i chose this cause it came after the other one.. here he had already suffered a lot and this just built it up..

They were both really heartbreaking though :(

bothhh :(

both but that was really cruel of elena how could she do i mean yeah he did kill her brother but he was in emotion state because of her and katherine and he was sorry for killing her brother he was just pushed over the edge

^^ yeah i agree that too 4 some 145 yrs he was suffering : (

both of them actually..:(

I think that was way worse...

awww... Felt so bad for my Damon :( I love how you say "sait stefan" lol

such a slap in the face

Both. But this more this was like world crushing, heart break. :(

Both sad.. :'(

BOTH made me crt!!

Both was very sad moment ever T_T

Of course, I was absolutely heartbroken when Elena told Damon that he lost her forever. However, this scene, where Katherine and Elena both told him that they preferred Stefan, was what broke him the most and was, most likely, the most painful moment for him. :(

I know the other one hurt really bad but part of him knows Elena was lying about her complete feelings for him. The thought of losing Elena forever probably scared him to death!!! :)

For me, it's this one by far. This is like tearing his heart out and stomping on it. Then, when he thinks that's over with, you take it, and you chuck it into a fire. haha. very visual, i know. But seriously, his hope of Elena having feelings for him are GONE. He waited 145 years for a woman, only to be told that she never felt anything for him in return. Not to mention, BOTH of these women are in love with his BROTHER. So much worse. With the 'losing (Elena) forever' thing, there is always a way to redeem himself in that situation. It'll just take time.

Both...:(

Both at the Same time
it must be very painful!!!