Elena’s having a normal moment with Jeremy and Bonnie as they look through Christmas stuffs, and Damon’s watching them from outside. She sees him and signals for him to come and join them, because she’s happy and she wants to share it with him, she wants him to be a part of it, to be happy alongside her. That’s just the sound of my heart breaking. But he doesn’t. Of course he doesn’t. I think this is one of those times where the age gap is evident. Elena of course has been through a lot in her young life, and in some ways it’s forced her to grow up, to be a lot more mature than most people her age, but deep down she’s still an 18 year old girl blissfully naïve at times. And she tries to cheer him up by inviting him to kiss her under the mistletoe, like her Aunt Jenna used to do to Logan Fell. She actually said that! How adorable was that though???
There’s so much she doesn’t understand, she can’t possibly understand the position he’s in right now. It’s actually impossible. Because Damon has over a century of baggage and crap, so Elena doesn’t get why it’s so easy for him to just believe her when she says it’s real. He desperately wants to though; you can tell just by the way he says “We can’t.”
It’s not her fault though, because despite the misfortune that’s been her life, one thing that was never lacking was love. Elena’s been loved until it made her nauseous. She tells him that he can’t keep telling him that it’s not real, that she knows it’s real and she knows he feels it, so why is he fighting it.” Not understanding that even the slightest possibility of this not being “real” is too huge a risk for him to take.
I’m not sure how much Elena knows about Damon’s past, or if she understands what it all means. But we the viewers know it’s been one rejection after the other for him, heart break after heartbreak, loneliness, disappointment, and ultimately giving up any slight chance of happiness because others *coughLexiCough* drilled into his mind that he didn’t deserve it, that he wasn’t worth it, that it was reserved for Stefan and other “good” people.
This is why he doesn’t intrude on Elena’s happy moment with Jeremy and Bonnie. He doesn’t belong there, he’s never belonged. His place is on the outside looking in, it’s always been and after over a century, he has no desire to pretend. *CRIES*"