Chris Brown's decision to nap during work hours finds him in the crosshairs with Captain Lee. Kate puts her stews through 101 training in order to get them ready for their next charter. The new guests prove to be a handful with indestructible livers and put the stews' new training to the test. Kate meets a cute sailor she nicknames Jesus and has a midnight rendezvous on his boat during charter. Matt faces his first challenge of the season with sushi dinner and a tequila pairing while Bruno steps up to the plate by dressing down in his skivvies to impress the guests.

Captain Lee makes a decision regarding the crew's re-configuration which rocks the team to its core. Matt's date with Brianna has an unexpected outcome when they mistakenly arrive at a nude beach. Jen grows weary with the unfair treatment within the Interior. Kate plans an anniversary surprise for the charter guests that fizzles. Meanwhile, criticism from the charter guests sends Matt spiraling into shame.