So this has got to be the hardest prompt of this entire meme. I mean, most fans of this show live for whatever riDONK funny thing Damon is going to say in any given episode. Narrowing it down to just one thing is very difficult. Therefore I have to take you through my thought process.
My initial reaction was something along the lines of "You know what, I do believe in killing the messenger. You know why? Because it sends a message!" (said to Isobel as he's throttling her in 1x21 "Isobel") or "I will shove this ring so far up your ass you'll really have something to choke on!" (Said to Jeremy in 2x02 "Brave New World" after he's throttled Jer and as he throws said ring at Jer's head so it bounces off painfully. Of course, this also follows the episode where Damon killed Jeremy, so it's even more chilling.)
I also thought of "And the evil, slut Vampire who only loved herself," as said to Katherine in 2x07 "Masquerade" but then I read my new friend
linsell_farm's
answer for this day in her journal and it made me reconsider my reasons for choosing what I've chosen. She talked about what he said, versus what he meant by what he said, and that's why I picked this:
This has been a no good, very bad day.
from 1x19 "Miss Mystic Falls"
Ian also looks so beautiful in this shot, but that's just a bonus *g*
He's referring of course to Stefan going off the deep-end. But he's speaking to Pearl and Anna, who have no idea what he's talking about. This is one of my favorite lines of dialogue because (1) of Ian's delivery (as always, so perfect), (2) of the reference to a childhood book I loved
Alexander and the Terrible, Horrible, No Good, Very Bad Day, and (3) intrinsically, it's his worry for Stefan--his love for his brother--and what would have happened if he didn't have Sheriff Forbes in his back pocket that has made it such an awful day. He doesn't even have time presently, in that moment, to realize that he and Elena had a heck of a moment when they danced together, and he doesn't realize they're about to have another one when, together, they handle Stefan's situation.
It's just about his brother, and the burden he's got on his shoulders. And, as my roommate said when I told her I'd finally decided to go with this line, "You do quote that one a lot." So there you go.