Random Question, but i don't understand. it seems like chandler tells monica he loves her for the 'first time' twice? could anyone explain?

Um, I'll try to answer this as best I can, hopefully it'll make sense too.

The episode you're talking about, TOW All the Flashbacks, or something like that, when its all about the thanksgiving flashbacks, and Chandler finds out about his toe and what not, is when Chandler really tells Monica he loves her. It let loose because she was trying to get him happy again because of the toe thing.

When Chandler cracks in TOW Everybody Finds Out, he's admitting to everyone else that he's in love with Monica. I don't remember if Monica was shocked at that, but if she was, most likely she was shocked because he finally admitted it to everyone else (with the exception of Ross).

So in quick words:
The first time, in TOW All the flashbacks, was when he admitted it to Monica that he loved her.

The second time, in TOW Everybody finds out, was when he admitted it to nearly all the friends, again with the exception of Ross.

Hope that clears things up a bit.

Well put, Livelifeup.

I also thought that in TOW All the Flashbacks, Chandler said he loved Monica somewhat off-handed and as a spontaneous reaction to her trying to cheer him up. When Monica goes "You love me?" Chandler kind of playfully tried to take it back, almost like he couldn't believe he said that out loud.

Getting to TOW Everyone Finds Out, Chandler openly and confidently admits to everyone that he's in love with Monica, which was a big thing, not just because it's a big confession, but because it's Chandler and he has a history of being a flake with love. And on another note, it was just a sweet moment! The cat was out of the bag, Joey could breathe a temporary sigh of relief, lol!

Just some added thoughts :)

Well, i think that the first time, on thanksgiving, he said it without thinking about, just saying what was subconciously on his mind.
The second time, hes saying that hes IN love with her, not just that he loves her.. idk if thats different for you but it is for me... :)