Preheat oven to 375°F (190°C). Line a baking sheet with parchment paper.
In a large bowl, cream together butter, granulated sugar, and brown sugar until light and fluffy. Beat in egg and vanilla extract.
In a separate bowl, whisk together flour, baking soda, and salt. Gradually add to the wet ingredients, mixing until just combined. Stir in chocolate chips.
Drop by rounded tablespoons onto the prepared baking sheet. Bake for 10-12 minutes, or until golden brown. Let cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely.
Prepare the pastry cream: In a saucepan, whisk together milk, sugar, cornstarch, and egg yolks. Cook over medium heat, stirring constantly, until the mixture thickens and comes to a simmer. Remove from heat and stir in vanilla extract. Let cool completely, pressing plastic wrap directly onto the surface to prevent a skin from forming.
Prepare the chocolate ganache: Place chocolate chips in a heatproof bowl. Heat heavy cream in a saucepan until simmering. Pour over chocolate chips and let sit for a minute. Stir until smooth.
To assemble the cookie bites, spread a small amount of pastry cream on the bottom of one cookie. Top with another cookie. Drizzle with chocolate ganache.
Notes
Enjoy your homemade Boston Cream Pie Cookie Bites! Store leftovers in an airtight container.