The Third Charter is aboard the My Seanna, but not the cushions, as the deckcrew fails to tie them down before allowing Captain Lee to take off. Chief Stew Heather complains to Captain Lee that Third Stew Jess is allowing problems at home to "leave the cabin" and effect her work. The high winds break the tie on the trampoline and it glides off into the Caribbean. Deckhand Wes channels David Hasselhoff and ludicrously grabs a jet ski to retrieve it. Luckily, First Mate Eddie is following in the tender to tow the trampoline in.
Lead Deckhand Jake is colluding with Heather to set Jess and Wes up on their night out. Deckhand Rayna awkwardly asks Wes, if Jess wasn't an option, who would he hook up with? Wes tells her that he doesn't ever think of people he works with "like that" in reference to her and uncomfortably Rayna acts disgusted at the thought.
Tanorexic Primary Guest Ronnie is turning 75 with an 80's themed birthday. Heather and Rayna lay the groundwork for an impending conflict when Rayna gives Heather an attitude about the theme night dress-up. Heather asks the deckcrew to help her serve, but to her chagrin, they keep bringing food to the table without serving utensils. In her talking head, Rayna states this is solely Heather's problem. In her talking head, Heather is annoyed her own crew isn't innovative enough to anticipate a lack of tongs and makeup for it while turning down cabins. The crew is too busy dressing up to help Heather with clearing plates. The crew brings out the cake and Eddie, dressed as a curly headed Hulk Hogan, tries to give Captain Lee a kiss on the cheek.
Heather sends Jess down to her cabin. Jess and Rayna talk about Heather's attitude and being mad at everyone else for her own mistakes. Fraser and Heather complain about Jess, who Heather describes as a bad apple who could rot their whole tree.
Docking into the Christophe Harbour goes perfectly. Heather discovers that Fraser has ownership of both closets in his cabin. The crew gets a $25,000 tip. Fraser is jealous that Captain Lee gave Jess a compliment at the tip meeting (for showing more of her personality at the 80's dinner).
The crew starts dinner with a shot that Fraser says tastes like nail polish. Jake and Heather flirt heavily. The crew quickly evacuates from the table to leave Wes and Jess together. Jake and Fraser flirt together. Jake pulls his pants half way down--Eddie tells him to pull them up, but Heather encourages him to take them off. A naked Jake and Fraser (who is in his underwear) jump into the pool. A game of truth or dare results in Jake and Fraser making out. Jake corrects Rayna that he isn't bisexual, he's sexually comfortable. Heather shows the rest of the crew the video she took of Jake and Fraser making out. Heather complains to Eddie about Captain Lee's praise of Jess taking down Fraser's esteem.
Jake wakes up still drunk. Captain Lee is working out in the gym. Eddie informs Jake that he made out with Fraser while blacked out. Heather shows Fraser the video she took of him making out with Jake. Fraser also had no memory of the make out. Fraser is mortified that he potentially ruined his best friendship on the boat.