Preheat oven to 350 degrees F.
Cut cherries in half (you should have 30-34 halves). Cut a small "v" at the top of each cherry half. This will make it look more like a heart. Using a few paper towels, dab off any excess liquid. Set aside.
Cream the cream cheese, butter, and sugar together until light and fluffy (1-2 minutes).
Add eggs, vanilla, cherry extract (optional), and red food coloring (optional but so fun). After mixing, if you want a darker pink, add a couple more drops of food coloring.
Next, add dry ingredients (flour, baking powder, and salt). Mix until dough forms. The dough will be soft but still able to come out of a cookie scoop.
Using a size 40 cookie scoop, place 12-15 cookies on a cookie sheet lined with parchment or a silicone mat.
Carefully press a heart-shaped maraschino cherry into the top center of each cookie.
Bake at 350 degrees F. for 12-13 minutes. Bottoms should begin to brown, peaks on the top of the cookie may start browning but the whole cookie should not be brown.
If over baked the cookies will be dry and crumbly.
Remove and place on cooling rack or paper towel. Once cooled, drizzle with chocolate.