In short, the answer is no. Their system is not sophisticated enough to determine if you obtained a beer in Bar A at 1:04PM then walked 15 feet and obtained a second beer in Bar B at 1:06PM that it would flag. Honestly, it does boil down to observation. The crew has been trained to identify people who are clearly taking advantage and attempting to drink two people off one package. So, if your super duper obvious; then they will stop you and basically rip up the package option.
At the end of the day, it boils down to whether you're ethical and seeking to steal free drinks for a second person. As pointed by Dave, this would be a violation of the guest conduct policy and I question if a free few beers for your friend is worth the hassle of the line contemplating evicting you from the ship.