Put the chocolate in a microwave-safe bowl and heat on medium for 1 minute. Stir and repeat until the chocolate melts, about 3 minutes in all, depending on the power of your microwave. Alternatively, put the chocolate in a heatproof bowl. Bring a saucepan filled with an inch or so of water to a very slow simmer; set the bowl on the pan (without touching the water). Stir occasionally until melted and smooth.
Process the cookies in a food processor until finely ground. (You should have about 1 1/2 cups ground cookies.) Alternatively, put the cookies inside a heavy resealable plastic bag and crush by moving a rolling pin over the cookies.
Stir the cookie crumbs, dried plums, confectioners' sugar, bourbon and condensed milk into the chocolate until evenly combined. Cover and refrigerate the mixture until firm enough to roll into balls, about 45 minutes.
Scoop a tablespoon or so of the mixture at a time into a small ball with a cookie or small ice cream scoop and set onto a baking sheet or large plate. Roll each portion by hand into a smooth ball.
Store the booze balls in an airtight container at room temperature for a day to allow the flavors to come together. Store the balls in the refrigerator for a week or freeze for up to 1 month. Roll in decorating sugars or wafer crumbs and serve.
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