Preheat the oven to 350 F degrees. Line a cookie sheet with parchment & set aside.
Combine the butter, cream cheese and milk. Mix well until smooth.
Add sugar and eggs & mix well to combine.
In a separate bowl combine flour, vanilla, salt and baking powder. Whisk dry ingredients together.
Add dry ingredients to the butter mixture a bit at a time, mixing in between additions, until all is incorporated. Fold in the chocolate chips and raspberry.
Use a medium cookie scoop to make rounded balls of dough. Arrange 12 on a cookie sheet. Wet your hands slightly, then gently press cookies flat and tap around cookie balls with fingers to smooth edges. Bake in a 350°F oven for 12-14 minutes.
Let cool on the sheet for 5 minutes, then transfer to a cooling rack.
Pour 1/4 cup semi sweet chocolate chips into a small bowl. Melt in microwave for 1 minute. Let sit 3-4 minutes in microwave, then gently stir. Heat additional 10-15 seconds, if necessary. Use a small spoon to drizzle on baked cookies. You can also transfer to a small baggie, snip the corner and pipe chocolate onto cookies. Let cool to set & enjoy!