Abstract: A tooth brushing system comprising a toothbrush head including a base defining a basal plane, a long axis and a short axis; and a multiplicity of bristles arranged in a plurality of bristle groups which may each have individual characteristics such as length and stiffness matching the differential anatomies of the various portions of the teeth, the base comprising a respective plurality of planar base portions, respectively supporting the plurality of bristle groups, wherein the planar base portions are configured to see-saw above and below the basal plane. Preferably, the handle is configured to retain a toothpaste-filled cartridge and the handle has at least one operative orientation in which the cartridge retained thereby is arranged to permit toothpaste to be dispensed onto the head. Optionally, a stabilizer is provided having at least one operative orientation in which it is fixedly associated with the head, the stabilizer being configured and arranged to roll along occlusal surfaces of teeth.