A toothbrush includes a head with an extendable handle. The toothbrush has a brush head with bristles extending from one side, and an opening containing one or more segments nested within one another. The inner-most segment is pulled outward, away from the brush head, with the adjacent outer segments following forming a handle assembly. A resilient member within the brush head between the head and inner-most segment assists in extension of the handle assembly. Upon extension the segments form an interference fit with each adjacent interior and exterior segment forming a rigid handle assembly. When the handle assembly is in an extended configuration a retention member extends from the interior of the segment surrounding the extended segment for engaging the end of the segment thereby preventing the handle assembly from collapsing. A rotatable collar at the end of the inner-most segment includes filament for flossing teeth.