As you make your list and check it twice, make sure you pack plenty of Gospel tracts! Besides the Christmas Cash, I've had a lot of success with the "101 of the World's Funniest One liners" too. There are a lot of retail clerks that are bored or waiting to get off their shift and this not only breaks the ice, but is also not your typical "boring" tract. It's really quite funny and has 101 quips and the Gospel message inside.
I went shopping with my husband at "Sportsman's Warehouse", which I imagine, is the equivalent of a man going to "Ann's Hallmark." He could spend hours in there as I try not to slip into a coma drooling from boredom. But, there were plenty of clerks who were ready for some excitement and I handed this one out successfully.
We also had dinner (just the two of us) and were able to witness to our waiter and the owner of the restaurant. The owner gave us his business card and told us to come back for a meal on him. Hmmm, maybe we'll go back and witness some more at that restaurant!
The clerk at the Hallmark store, the hostesses at restaurants, the man selling newspaper subscriptions at the grocery store all received tracts and conversation about the Law and Grace.
Not all conversations can be in-depth due to the fact that they are working. But, try handing out tracts wherever you go. If you still can't work up the courage to hand some out, at least leave some in the restrooms. Just take baby steps and you will find that it won't feel as foreign to you the more you do it. But, I must confess, I still get nervous and almost chicken out almost every time I begin talking to a stranger. Don't let that stop you. Rely on the Lord to give you the words to say. Your obedience will be honored. He doesn't ask for the eloquent, the PhD's, or only pastor's to speak. We are all called to walk a life of obedience.
By far, Christmastime is my favorite time for handing out tracts. Not only do you not need to come up with a good opening line, since Christmas is about Christ, but people are just happier and seem to be in festive moods. I've experienced no reluctance from people to take a tract during this time. If you've never handed out tracts before, this is the perfect time for a beginner to start.
If you have never shared your faith and call yourself a Christian, examine the scriptures and see what the Bible has to say about sharing your faith by actually opening your mouth. We don't all have to stand on a street corner and preach. But, we are called to be faithful witnesses and if you are only "kind" to people and mention occasionally that you go to church, they are never going to see their absolute need of the Savior. To have never opened your mouth to share the hope you have is, in my opinion, denying Christ by omission. Sadly, in the past, I would let months or years go by without engaging a single person in a conversation about Christ. Don't live in the past. If you've never shared your faith, start now! You'll never regret it.