I first had fried pickles long ago, before they were a popular item on many restaurant menus. And I think over the years, I've perfected a pretty tasty recipe - but there are specific rules to follow:
Heat canola oil (med-hi) in a cast iron skillet about a half-inch deep. Let that heat while you prepare the pickles.
Purchase dill pickles that are thickly cut (I like Best Maid brand). Set up your station - a bowl of an egg/milk mixture, a bowl of seasoned flour (Cajun seasoning and season salt), and an empty plate.
Take out your pickles and drain them on paper towels and pat them dry. Taking about 5 at a time, dunk them in the egg/milk mixture, then coat in the seasoned flour, then place on the empty plate. After all pickles are breaded, test your oil to see if it's ready. Place one pickle in the oil and if it sizzles, it's ready.
Using a large slotted spoon or wire scoop, take about 8-10 pickles, shake off loose flour, and carefully place in the oil. Prepare a basket lined with paper towels to receive the fried pickles.
The pickles will brown pretty quickly, and when they do, use your spoon to turn them over (do not crowd the pan).
Carefully lift the pickles out onto the paper towels, and continue frying.
Lightly salt with kosher salt while hot, and before serving.
Now, instead of just Ranch dressing for dipping, I use mostly salsa (freshly made or fresh in the store's refrigerated section) and just a bit of dressing on the side. Mix it as you dip - and it's most delicious!
There are the steps that must be followed in order to have crispy pickles that are not greasy and soggy and all stuck together!