Years ago I was sitting on a bench on a road on what was one of the loneliest days off I had had. I wasn't overly happy with life and the world at that moment in time, and I found myself sitting, watching traffic for what must have been a very, very long while.
All of a sudden this girl walked past pushing her bicycle along. She looked sweet, and nice, and so I smiled, and she smiled back. She continued along, and I continued to sit there, but the idea was planted, and I figured that the day was already bad, so how much worse could it really get? A few moments later I caught up to her, introduced myself, and we walked along chatting. We swapped numbers and ended up as an item for about a month after that.
At that moment when I approached her, I didn't really care what happened. I think having no fear of rejection is probably the best start, but the problem with that is having no fear requires either: 1) A very low self esteem at that point in time, or 2) A massive ego. I don't really recommend either, but they can sometime pay off in the strangest and most unexpected ways.