Part of mid- game is developing a connection, by some chit chat; however, I, like many guys here constantly run into awkward silences. Well I found the answer a couple of weeks ago, from some old school PUA called juggler. He gives courses on how guys can become a great conversationalist, his website is charisma arts. com. Check him out on youtube.
Basically the cure is to just state an open ended observation about the situation or yourself. It can be anything, within reason ofcourse. So for instance your out, and your working on your day game, you've opened and you can feel the conversation running out, here's where you make the observation:
EG> "It's cloudy, looks like its going to rain""I love the mall" "looks like an interesting book?" "I hate shopping for clothes" "what did you get" "look at that guys t-shirt".
Just stop straight away after, let the women hear the silence, so she will women answer, and the conversation will continue to flow.
I have definately found the more honest you are with the observation, so for instance whether the observation actually genuinely interested you, the better the response you'll get.

Is that the Juggler from Neill Strauss's book?

Will deffo check that stuff out

The very same, he's a bit of a legend, he did some channel 4 programme as well, ages back. I think wikipedia might have some details about what its called, if your interested. . .