The roommates arrive at the boat, and Brian (the boss) introduces himself, and his assistant Matt. Brian says that he and Matt will teach them how to sail on their boat, the Stars and Stripes, which was in the America's Cup. Cameran interviews that it's a great opportunity. Brian introduces them to Troy, who owns the boat and started their company. Brian asks if any of them have any sailing experience, and only Cameran raises her hand. She says she's been on a sailboat, but that she's never been the one controlling it. That's like saying you have experience driving because you've ridden in a car before. Shut up, Cameran. Brian asks if they all know how to swim, and Jacquese says that he doesn't. Brian promises that someone will teach him. Brian says that they run corporate charters and public excursions, and that the roommates will serve as the crew. Frankie interviews that this job is definitely not her thing. I just noticed that Frankie wears a ring on the third finger of her left hand. Is she engaged? Brian tells the roommates that this is a serious job, and he recommends that they show up to work feeling one hundred per cent, because he won't let them go out otherwise. In other words, don't show up hung over and puking. Wow, I wonder if that will happen.

Troy offers to get Jacquese a "comfortable life jacket." Jacquese cracks me up when he says that he doesn't care if it's comfortable as long as it saves his life. Brian says that Jacquese, Brad, and Cameran will be learning on one boat, and that Robin, Jamie, Randy, and Frankie will be on the other one. Brad says that they are "Team Bazooka Joe." Jacquese puts on the smallest life vest ever; like, it's seriously child-sized. Cameran interviews that she feels bad for Jacquese, because it must be embarrassing. It would be more embarrassing if he drowned, wouldn't it? Well, not embarrassing so much as shitty. Also, I have a fear of life jackets. That was so not cool, Jacquese.

The roommates learn how to sail. Brad, Cameran, and Jacquese seem really into it. Frankie raises the sail on her boat and gets excited that she is in control. Sailing, sailing, and more sailing. Frankie spots a warship and freaks out. Isn't there a huge naval base in San Diego? I'm going to bet that huge boats are a common sight. Frankie interviews that she's ready to quit. Maybe she should. Jacquese, on the other hand, is jumping right in. He even gets to steer the boat. Frankie sees a tanker or something, and puts her head down. Jamie tries to comfort her. Is anyone feeling like this just isn't going to work out? Can't Frankie work in the ticket booth or something? Jacquese interviews that if he's going to be a sailor, he's going to be the best one there is. The editors play a sea chantey while Jacquese steers the boat.