A finger engagement assembly for supporting a handheld dental tool on a user's hand. The finger engagement assembly includes a mounting member with a cylindrical shaped body extending along a grip axis and having an aperture extending there through. The mounting member has an inner surface that interfaces with a dental tool and an outer surface that interfaces with a finger engagement. The finger engagement includes a rotational coupling extending about the mounting member and is operable to rotate relative to the mounting member about the grip axis. A post extends from the rotational coupling in a first direction and supports a crossbar. The crossbar extends across the backs of a user's index and middle finger and is functional to retain a handheld dental tool, such as a dental mirror, to a user's hand, while allowing the dental tool to rotate relative to the finger engagement.