hhmmmmm.....I have several people in my life that I have no problems sitting in silence with (it isn't awkward). I'm just super comfortable with those people....they're like my kindred spirits :) My hubby and I sit next to eachother all the time and don't talk and my heart is perfectly content, at peace, and joyful even. So if this is what you mean than yes, yes I have :)
No. If I feel like I've had an amazing conversation I make sure to tell the other person that. Sometimes we only have once to touch another person life and when that happens I feel the gift should be acknowledged - adds to the joy!!!