Put strawberry flavored gelatin and boiling water in blender container, blend at low speed until gelatin is dissolved. Pour 1/2 cup of gelatin mixture into measuring cup; set aside.
Add half the milk to remaining mixture in blender container, blend on low speed until mixed. Add half the strawberry ice cream, blend until smooth. Pour into tall glasses. Repeat with reserved gelatin mixture, milk, and ice cream. Garnish each glass with a fresh strawberry, if desired.