Preheat your oven to 350°F. In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until fluffy—about 2 minutes with an electric mixer. The mixture should look pale and light. Beat in your egg and vanilla extract until everything's combined smoothly, then set this bowl aside.

In another bowl, whisk together the flour and mix it into your butter mixture. Stir until a soft dough forms—don't overmix or your cookies will get tough. You want the dough to come together but still feel slightly sticky. This is the cookie base for your strawberry cheesecake stuffed cookies.

Now make the filling. Beat the softened cream cheese, powdered sugar, and heavy cream together until fluffy and spreadable—about 2 minutes with your mixer. Fold in the finely chopped fresh strawberries gently so they don't break down too much. You want little berry pieces visible throughout.

Scoop the cookie dough into 16 portions using a cookie scoop or tablespoon. Press each scoop onto a parchment-lined baking sheet, creating a flat disc about 2 inches wide. The dough spreads as it bakes, so leave space between each one.

Make an indent in the center of each cookie disc with your thumb, creating a small pocket. Spoon about 1 teaspoon of the cream cheese mixture into each indent. Don't overfill or it'll leak out the sides while baking—I learned that lesson.

Bake for 12 minutes until the cookie edges turn golden but the centers still look slightly underbaked. The cookies will look a tiny bit raw in the middle when you pull them out—that's exactly right. They firm up as they cool, and that's what keeps your filling creamy.

Let the cookies cool on the baking sheet for 5 minutes before transferring to a wire rack. They'll be delicate when warm but gain strength as they cool down completely. Once cool, refrigerate these strawberry cheesecake stuffed cookies for at least 30 minutes before serving.