Are you supposed to floss or brush first or does it really matter? Also how many times a day should you floss?

Floss then brush. Ideally flossing first will remove the plaque and food debris that sticks to the sides of your teeth and brushing will remove that and the plaque that builds on the front and back. Floss twice daily would be ideal. Key and best results are from doing both twice a day.
No difference! . No matter who says what .. There is no scientific research to show which one should be done first. ! the important point is brushing and flossing should both be done.. And in whichever sequence you like ... If u can floss correctly after each meal, that will be the ultimate, but realisically if u do it even once every night you will be in good shape.