To a large bowl, add the peanut butter, vanilla, softened butter and confectioners sugar. Mix very well with your hands, almost kneading it like dough.
Add more confectioners sugar if you need to, but only a tablespoon or two at a time. The dough should not be sticky. You should be able to roll it in your palms without it sticking to them.
Roll the dough into balls. They should be about the size of a ping pong ball or smaller. If they are too large, they will be too heavy to dip in the chocolate.
Place rolled balls onto a wax paper-lined baking sheet. Place in the freezer for 10-15 minutes while you work on the chocolate.
Melt your chocolate and shortening by either using a double boiler or in the microwave. See notes above.
Remove dough balls from the freezer. Grab a few toothpicks to have handy. Line another baking sheet with wax paper and set the two baking sheets next to one another and your chocolate nearby.
Prop your chocolate bowl up at an angle so the chocolate is pooling to one side. Pick up a dough ball and place the toothpick in the center. Gently dip it in the chocolate, leaving some undipped at the top (to look like a buckeye). Gently shake off excess chocolate. Place dipped buckeye on new wax paper-lined baking sheet, gently pushing it off the toothpick with your finger (touching the undipped part).
Repeat with other dough balls. If your dough balls become too warm or are slipping off of the toothpick, pop them back in the freezer for a few minutes. Replace your toothpick every once in a while as the peanut butter builds up on it. Reheat chocolate if it becomes to solid.
Once buckeyes are all dipped, place them in the refrigerator and allow chocolate to set. Keep refrigerated in an air tight container.
