4: Awkward silence pressures

I wish I could have a little voice in my head that would stop me before I spoke. It would say "Shut up. Awkward silence is better than whatever you are going to say next." But without this voice, I ramble. I say whatever comes into my head. I tell someone about a movie that they really wouldn't like, that I didn't even like. I tell them about a moral debate that I am having with myself and then if I do manage to get them discussing this topic, I inevitably control the conversation because I have the home court advantage. The debate is in my head.
My adviser is extremely friendly and does not know what to do about someone else being socially awkward. I don't know how he has managed to live in the math world this long without screaming at anyone. Given a few seconds of silence as we walk somewhere, I have bored him by telling him about my new shoes (complete with details about my foot problems, always exiting to hear) my random health problems, my cleaning schedule, my little cousins, etc. I'm sure I was interrupting something that was already going on in his head. It may not have been interesting, but at least it was holding his attention.
Where do other people learn to make conversation. I know I need to learn to ask questions instead of talking about myself, but what can I ask? I open with "How is your week going?" and then I am stumped. My mind is constantly moving from thing to thing, so I just start talking about getting new glasses. I'm afraid if I tried to ask questions I would end up saying something like "Do you have any foot problems?" out of the blue, because of my stupid flow of consciousness.
Lets say I notice something about someone during a silence. They added highlights to their hair, for example. Now, it would have been polite to notice this earlier, but I did not. Do I point it out now? Is "I like what you did to your hair" good enough? What if they don't like how it came out? What if they actually did it 2 weeks ago? What if highlights are something they think is subtle and pointing it out defeats the purpose (sort of like "I like how you covered up the grey!" or "Good job masking that blemish!") What if they say "thanks" and we are left with another silence. This time, a silence that follows the introduction of a new topic. Is it rude to open with another non sequitur? Or must I continue on the vein of hair? What more can I ask? Did you have it professionally done? That is dangerous.
Today's annoying thing is really me. Me in normal situations.