A coupling assembly for removing contents of a container from an opening in the container. The coupling assembly includes a container insert coupled to the container opening, the container insert including an insert passage, and an insert vent path extending through the container insert. The coupling assembly also includes a unit including a unit cavity, a valve assembly positioned axially therein, and a unit vent path. When the unit is coupled to the container insert, the insert vent path mates with the unit vent path to create a complete vent path extending from within the container to a vent port on the unit, and the valve assembly opens to place the insert passage in fluid communication with the first unit cavity.