Preheat the oven to 350 degrees F.
Prepare a baking sheet by lining it with parchment paper.
In a stand mixer, add the softened butter and beat the butter on medium high speed until it has lightened. This should take about 30 seconds.
Adjust the mixer’s speed to low and continue mixing while adding in the vanilla extract, powdered sugar and flour.
Once the ingredients are combined, begin adding the milk 1 tbsp at a time while mixing on low until the dough resembles a shaggy ball.
Add some flour to a clean countertop and use a rolling pin to roll the dough out to about 1/4 of an inch thick.
Use a 2 inch heart shaped cookie cutter to cut out the hearts and transfer them to the baking sheet.
Roll out any leftover dough and repeat the steps until you’ve used up all of the cookie dough.
Transfer the cookies to the freezer for 15 minutes so they hold their shape.
Bake the Valentine’s Day cookies at 350 degrees F for 12-15 minutes or until the bottoms have slightly browned.
Remove from the oven and transfer to a cooling rack to finish cooling completely before adding the icing.