Place a saucepan over medium high heat. Add 2-3" of frying oil to heat up to 375F.
Set up the battering station with three bowls. In the first bowl, mix the flour and seasonings. In the second bowl, add the beaten eggs. In the third bowl, mix the breadcrumbs and grated parmesan.
Slice the aged cheddar into tiny pieces, then gently press into the centers of each pitted olives.
Dredge the cheese-stuffed olives in the flour, then the beaten eggs, then the breadcrumb mixture. If desired, you can double coat by dredging through the flour, eggs, flour, eggs, then breadcrumbs for extra crunch.
Fry in small batches for 2-3 minutes, until deeply golden and crispy on all sides. Garnish with more freshly grated parmesan to serve.
To make the dipping sauce, mix all ingredients together until smooth. Enjoy with the fried olives while warm!