Cook the tortellini according to the package instructions. Once tender, drain and give a quick rinse under cold water to stop the cooking. Set aside to cool completely. You want the tortellini chilled, not warm, for easy skewering.
While the tortellini cools, grab your block of pepper jack cheese and slice into bite-sized cubes. An easy way to get even pieces is to cut the block into 3 lengthwise and 6 widthwise. You should end up with 18 pieces total.
Now it’s time to assemble! Add an olive to your appetizer skewers (or long toothpicks). Next, thread on a cube of pepper jack cheese. The sharp, creamy flavor adds a nice contrast to the rest of the ingredients.
Fold one slice of pepperoni in half, then fold a second slice in half the opposite way - so one fold faces forward and the other backward. Stack them and slide both onto the skewer. This gives the skewer a little extra texture and flavor in one bite.
Finish off by adding one tortellini to the end of the skewer. The pasta helps anchor everything and rounds out the bite.
Once all your skewers are assembled, you can serve them right away or pop them into the fridge until you’re ready. You can drizzle a little Italian dressing over them before serving, if you like.