I was at a public event yesterday, not a massive one, but about 300 people in a self-contained space. It was mostly families, so there were a fair number of people who were not paired up from the ages of 15 to 30.
There were several attractive girls and young women there who appeared to be unattached. There were also a number of good-looking young men. What I found interesting is that at no point did I see any of the young men attempt to talk to any of young women. That doesn't mean it didn't happen; I wasn't paying much attention to any of them. But I saw no signs of any young men even attempting to speak to anyone outside of their own little groups, which normally one would expect to have occasionally observed over the course of several hours.
This is the very first principle of Game a man has to accept: be proactive, not reactive. If you see an attractive girl, don't wait for "the right moment", but go and talk to her. Start with "hello". This is not necessarily with an eye to getting her number or finding out if she is taken, but simply to get oneself into the habit of speaking to attractive women as a matter of course. It's really not that hard.
If you're a single man, set a goal of approaching and speaking to seven female strangers this week. That's just one per day. Nothing fancy, no pressure, just going up and speaking to them, even if it's only to ask them the time. The objective is for it to become so natural that you will no longer suffer approach anxiety when you come across a woman in whom you are actually interested.