Well any season after the third one.

Season 4.

I think Season 3 if DE r taking time to develop stronger. Maybe by the end of S2 Damon admits aloud to himself (or maybe Alaric) that he loves Elena. Possibilities...

I think Damon is a person who shows his love in stead of saying it. I think he might tell Elena he loves her after season 3. Personally, I prefer it if he uses other words than "I love you" because these words have been used too much and I like to think that Damon and Delena are more orignal and special than anyone else. Or he might say these words just in another way that is totally Delena-like.

Anyway, I am not stressing over him SAYING it, because I know that their buildup and development of the relationship will be more important and make them so much more amazing, and that is more important than the words themselves. They will show each other that they love each other and at some point, the words will be unnecessary :)

^^^Haha, I was waiting for you to comment, your ones are always very detailed and interesting to read! Yeah, I completely agree, actions speak louder than words and Damon is all actions. Damon and Elena always manage to say things to each other without actually saying it. Like they both care deeply for each other and we all know that but did they say it to each other, no. But the things they do (like saving each others asses) shows that. I dont think its important for them to say that they love each other but show it more and im sure they will be showing it a lot as the seasons progress. So, if Damon does ever say "I love You" to Elena(i mean the actual words not other words that mean the same thing) which im sure he will then he'll probaly say it at the last season but he will definately imply it during the show and hopefully so will Elena!

^ Aw thank you Resha :) You're too nice to me ;)

Actually, I dont think TVD will go on for more than 5 season IMO. I dont WANT TVD to go on for more than 5 seasons actually. I want them to end on a good note, where people are not tired and sick of them. So by choosing seaosn 5/6, you and I agree about him saying it in the last season of the show ;)

Oh lets hope they're going to have more than 2 seasons lol. I think 3 or 4 if not this season.

Yea, they should leave it a while, to aloud build up for their relationship. So they have a much more epic relationship than Stefan and ELena. (Well they already do). It's just so much better, with build up.

On the season 2 season finale

3/4 hopefully! :)

on the season 3 finale :)

halfway through season 4

and i really doubt the show will go beyond 5 seasons....i do not want it to

Maybe in S4!

4th or maybe 5th...

possibly season 2 finale. But season 3 is good for me. here's my fantasy lol

Like in the books, stefan will propose and Elena will be deciding cause she;s got all these feelings for Damon right? So she'll talk to him and he'll be upset inside but won't say anything. So he'll beg her not to marry Stefan and she'll ask him why. Damon won't answer so she becomes persistent.

"Please don't marry him Elena" blah blah blah.
then they'll start fighting and arguing and he finally kisses her. there we go! a shut up kiss and he wouldn't say "I love you" until later on
ROFL like that'll ever happen

Gosh let's hope he won't take that long!

Yeah! I'd Say. The Finale.

Not in S2 because that would be too much like Chuck and Blair from Gossip Girl and Damon and Elena are different - Season 4 or 5, or 6, at the latest.

why would he wait till season 5? that's like 4 years from now:/ besides he already knows something is up, he won't be able to hind it for too long, it will show...

I think season 3 but hopefully it won't be enough and she picks Stefan instead