A toothpick assembly that is engaged with a cover and is movable between extended, partially extended and retracted positions relative to the cover. The toothpick assembly includes a base with first and second ends a locking assembly provided at the first end of the base that secures the base to the cover and a toothpick provided at the second end of the base. The toothpick includes first and second regions. The first region defines sinusoidal grooves in the side faces thereof and a row of bristles extending outwardly from each groove. The bristles are integrally formed with rest of the toothpick assembly and taper in length from the base and towards the second region. The second region is bristle-free and terminates in an upwardly curving tip. The first and second regions taper in width moving toward the tip so that toothpick is easily inserted into an interdental space.