Remove one dough disk from the refrigerator at a time so that dough stays cold. Generously sprinkle flour under and on top of dough. Using rolling pin coated in flour, roll each dough disk out to about ⅛ to ⅙ inch thickness.
With a heart-shaped cookie cutter, cut out 24 sugar cookies and place on the two baking sheets lined with parchment paper. (If dough has warmed during rolling and cutting, chill in refrigerator for 10 more minutes before baking.)
Bake for 10-12 minutes (rotating halfway through) until bottom edges are very lightly brown. Don't over bake!
Allow cookies to cool a couple of minutes on the baking sheets before moving them to a wire rack to finish cooling.
Make the Buttercream Filling
Using a handheld mixer or a stand mixer fitted with a paddle attachment, beat butter on medium-high speed for 5 minutes until light and fluffy.
On low speed, slowly add powdered sugar one spoonful at a time, until just combined. On medium speed, mix in raspberry preserves, heavy whipping cream, vanilla extract, and pink gel icing coloring, until completely combined and smooth.
Place buttercream in piping bag.
Assemble Sandwich Cookies
Turn one cookie over and pipe buttercream evenly, covering the whole cookie. Press another cookie on top so that filling oozes out the sides slightly. Smooth edges with a spatula or your finger.
Insert a cake pop stick in the bottom of the sandwich cookie. Repeat for remaining cookies. You should have a total of 12 cookie pops.
Chill in the refrigerator for 30 minutes.
Make Chocolate Coating
Melt milk chocolate chips in a double boiler. Add 1 Tablespoon vegetable oil and stir until smooth. Pour into a small heat-proof cup that's deep enough to submerge the whole sandwich cookie and just wide enough for the cookie to fit inside.
Repeat the same process for the white chocolate chips, reserving ¼ cup in a separate small bowl for drizzling of cookies. Add 2 drops pink gel icing coloring to the white chocolate coating bowl and stir.
Coat with Chocolate
While chocolate is still warm, dunk each sandwich cookie pop into the melted chocolate, covering completely. (Six in the pink and six in the brown.)
Lay on a baking sheet lined with parchment paper. Take the reserved melted white chocolate and drizzle with a spoon (or a piping bag with a small piece of the tip snipped off) over the top of the coated sandwich cookie pops.
Chill for 15 minutes or until set. Serve and enjoy!