A toothpick assembly including a toothpick and a case within which the toothpick is detachably engaged. The toothpick includes a tapered tip which is generally triangular in cross-section having opposed sides connected by a generally flat end and an apex. A bristle array is provided on each side and the end and apex are free of bristles. The bristle array is configured as a sinuous or serpentine wave. Bristles in each array are smallest closest to an end of the tip and progressively increase in size as you move away therefrom. The toothpick is movable within the cases bore between a fully retracted, a partially extended and a fully extended position. A locking mechanism selectively locks the toothpick in any of these positions. When the toothpick is to be changed, the locking mechanism is disengaged and the toothpick is slid out of the bore and is replaced with another toothpick.