If you are truly dark brown stick to reds that have the numbers 2,3, or 4 in front of them. If you want to avoid Orange make sure the red has a little bit of a pink or violet cast. If you like it really vibrant you will need to do two steps. buy lightening powder and developer, or from a cubs or Walgreen something that says frosting or lightening, and mix it with shampoo. Lather damp hair with the mixture until it looks reddish Orange then rinse. This Is less damaging then the bleach on its own. If using permanent red wait 24 hrs before applying the red. If using manic panic or Pervana vivids, or another great long lasting one called Jerome Russel punky colors, (available at ulta), then you can use it immediately after rinsing out bleach mixture.