If you like your cute boss, and he's worried about keeping his bar afloat, you should definitely jeopardize his chances for keeping it in business, by working as an under-age server, and arranging a trespassing event on someone else's property.
Yeah I was so waiting for the cops to arrive and shut everything down and arrest him.
Also, not sure what state they are in - but does statutory rape not mean anything to Carter? Depending on the laws in their state (and what laws they want to make up for the show) it's a possibility that continuing any physical relationship with her being under 18 and him being 25 could cause him to be charged and put on the sex offenders registry.
You just know with the drama that is this show it's probably exactly what will happen.
Riddle wrapped inside an enigma, wrapped inside a taco.