In a large skillet, cook the bacon for 5-7 minutes or until bacon is almost done but still pliable. Let cool on paper towels.
While bacon is cooking, bring a large pot of water to a boil. Add the tortellini and the broccoli and cook for 7 minutes. Drain.
Preheat oven to 350 degrees. In a muffin tin, use a precooked piece of bacon from step 1 to line the inside wall of the muffin tin wrapping in a circle (not on the bottom). Use kitchen scissors to cut bacon to fit. Take another piece of bacon and zigzag it on the bottom of the muffin tin, covering the bottom of the tin. Repeat with remaining bacon.
In a large saucepan, melt the cream cheese and cream over medium heat, stirring until smooth. Add the pesto and stir until combined.
Add the drained tortellini and broccoli to the cream sauce in the pan. Stir to coat.
Spoon tortellini mixture into the bacon cups, filling as much as possible. Bake for 5-8 minutes or until warm. Top with grated Parmesan if desired before serving. Serve warm.