I start by beating the softened cream cheese in a large bowl until it is completely smooth, with no lumps left behind. Then I add the powdered sugar and vanilla extract and mix again until everything is fully combined and silky. This base needs to be smooth before you move on, since any lumps here will show up in the final texture.
In a separate bowl, I whip the heavy cream on medium-high speed until soft to medium peaks form. This usually takes a few minutes, and I watch closely so I do not overwhip it into butter. Whipped cream is what gives the filling its light, airy quality, so this step is worth doing carefully.
Next, I gently fold the whipped cream into the cream cheese mixture using a rubber spatula, working in broad strokes to keep as much air in the mixture as possible. Once it looks mostly combined, I fold in the diced pears so they are evenly distributed. The filling should look fluffy, pale, and speckled with little pieces of pear throughout.
I spoon a layer of graham cracker crumbs into the bottom of each cup, followed by a generous layer of the cheesecake filling, then repeat until the cups are full. I always finish with the cheesecake layer on top so it looks clean and inviting. Pressing the crumbs down lightly with the back of a spoon helps them hold together as a base.
Once the cups are assembled, I cover them and refrigerate for at least 2 hours, though I usually go closer to 4 hours for the best texture. This chilling time lets the filling firm up and the pear flavor settle into the cream cheese base. Skipping this step leaves the filling too soft to hold its shape.