Using a double boiler, melt the chocolate and mix until smooth.
Pour the chocolate into the silicone mold.
Carefully flip the mold over so that the chocolate can fall back into the pot. This will leave you with a chocolate shell.
Using a standing mixer, combine the brown sugar, butter, salt and vanilla and mix until combined.
Mix in your milk.
Gradually mix in the flour and chocolate chips.
Scoop about 1 tablespoon of the cookie dough into your hands and lightly press down into the chocolate molds.
Cover the top of the molds with a layer of chocolate.
Place into the fridge for overnight.
Remelt the chocolate and place into the piping bag.
Carefully remove the chocolate hearts from the molds and place onto a cookie sheet.
Cut the tip off the piping bag and drizzle the chocolate onto the hearts.
Let hearts harden for 20 minutes.