This is a French classic.

Get a jar of chestnuts in vanilla syrup and some heavy cream to whip. Pick up some sensational vanilla ice cream and great chocolate (like Valrhona or Lindt bittersweet). Scoop the ice cream into two wine glasses. Spoon the chestnuts and their syrup over it and top with little mountains of whipped cream. Between spoonfuls, take bites of the chocolate. After that, you are on your own.