One of the hardest things to do in personal witnessing is getting the subject of spiritual things up. How do we go from, "Nice day, isn't it?" to "Have you been born again?" It is probably the #1 reason many people do not share their faith. They just don't know how to get started.
I know how frustrating it can be to have the desire to approach someone, but chicken out because I just couldn't find the right way to open it up. I imagine all sorts of different scenarios in my mind while trying to come up with the best opening line. If I say this, then he might say that, then I could respond with...
The biggest fear is saying something that turns him/her off and turns the whole thing into a disaster and embarrassment. That is why I love to use good gospel tracts. If you get your hands on a good tract, it can open the door up for you and transition a pleasant conversation into a witnessing opportunity smoothly. Once the ice is broken, you are off and running with the gospel.
Today, a dear brother named Shawn and I hit the streets and employed this effective technique. We primarily used the curved illusion tract (pictured) to have a little fun with people before we began to share the gospel with them. We also used some fake money tracts, which are always a great hit, and had a lot of wonderful encounters with men and women where we were able to get into long conversations.
The tracts that people enjoy are great because it helps you earn the right to witness to them. It is awkward to approach people and immediately begin opening up spiritual things to them, and some even find it offensive. We need to make some sort of connection with them first and smoothly go from one subject to the next. The curved illusion is a great example. There are other great tracts you can use that are fun and easy to use at www.livingwaters.com