Chelsea telling Sarah not to forget her passport is the first indication that many of the staff get that Chelsea is organizing one of her infamous trips, this time back to Cabo San Lucas. She rents a private jet that can only hold herself and ten other passengers, those other ten chosen however Chelsea decides at any given moment. With one spot gone, Brad, Heather and Jiffy in particular do whatever they can to get on Chelsea's Cabo list. But as more and more spots get taken, the three of them get more and more desperate. Meanwhile, Stella, the infant daughter of Kit, one of the staffers, is in the office for the day since Kit had no other child care option. Chelsea and the writers try to tread lightly around Stella, not wanting to be a bad influence, but Stella may already have a mind of her own, even at her tender age. And Jiffy believes that being the office whipping boy is a sign of respect.