Soak the toothpicks in water for 30 minutes prior to cooking. This is to prevent the toothpicks from burning while in the oven.
Preheat the oven to 375 degrees Fahrenheit.
In a bowl, combine the cream cheese and pepper jack cheese. Thoroughly mix.
Boil the jalapeño halves for 2 minutes in a pot of water with a pinch of salt. They should soften, yet still feel slightly firm. Remove from heat and strain out the water.
Stuff each jalapeño half with about a tablespoon of the cheese mixture, and then wrap the jalapeño with a bacon slice. Secure the bacon in place with a damp toothpick.
Bake in the oven until the bacon is the perfect shade of brown (5 to 10 minutes).
Alternatively, you can cook these stuffed jalapeños over an outdoor grill. For a spicier side, do not boil the chili halves. Stuff them raw and bake. This will increase the overall heat and crispness of the jalapeños.