My button stays on high if I press it once, what did I do wrong?
From what I can tell from your drawing, you have both sides of your button tied to 5V.  The green wire on one side and the blue wire through the resistor on the other.  So yes, the button will always read HIGH.  

Instead, remove the resistor, tie one side of the button to the pin and the other side to ground.  Use INPUT_PULLUP in your pinMode cal instead of just INPUT.  Now a pressed button will read LOW and not pressed will read HIGH, so you'll have to reverse your logic in your code.  But the wiring will be much nicer.