My ideal conversation is probably more like this
Person X: I had a bad day because I just couldn't get anything done.
Person Y: I'm sorry to hear your day didn't go so well, what was up?
finish listening, pause while thinking of a reply
Person X: I just couldn't believe that balloon hoax and how everyone was fooled.
finish listening, pause while thinking of a reply
Person Y: I know exactly what you mean. I saw that on the news and it just dumbfounded me.
Person X: I was just so mad.
finish listening, pause while thinking of a reply
Person Y: I don't blame you. Can you imagine what they are going to do to the parents?
I definitely wish no one believed in "akward silences". But, knowing that a lot of people do consider silence akward, I worry that silences will make someone I'm getting to know uncomfortable, which makes me uncomfortable. I'm getting less uncomfortable about that, though. It's still a hassle to have to act pushy in group conversations, but I don't see any way around that. I think with my current bf I have the problem the OP mentioned that he thought I really was the pushy person I was acting like when he met me (in a group situation), and he's disappointed that I'm not. It took me a long time to realize that.