Combine flour, pecans, and butter in a bowl; press into the bottom of a 9x13-inch baking dish.
Bake in the preheated oven until crust is lightly browned, about 20 minutes. Cool completely.
Mix 1 1/2 cups whipped topping, cream cheese, and confectioners' sugar together in a bowl; spread over cooled crust. Layer pineapple over cream cheese mixture layer.
Beat milk and pudding mixes together in a bowl until thickened and creamy; fold in bananas and spread over pineapple. Layer strawberries over pudding mixture; top with remaining whipped topping. Refrigerate until completely chilled, about 2 hours.
Drizzle chocolate syrup over whipped topping layer and arrange the cherries equally apart from each other so each piece gets 1 cherry.
