Joe and Helen go on their first date and Brian hires high school student Kenny McElvey as a backup pilot for the grounded Joe.

Concerned by Helen's persistent anger over her break up with Joe, the rest of the group convince her to seek help with a transition group, not realizing exactly who the group is for. Meanwhile, after escorting Helen to the group meeting, Brian becomes obsessed with talking about Carol and takes over the group.

The sad news of Richard Kingsbury's death in Maimi is occasion for celebration at Sandpiper, as Kingbury's oldest daughter hires the Hackett's to bring the body back to Nantucket for the Memorial. But the brother's fly the wrong body back to the island, and it's up to Joe to impersonate the late Kingsbury at the funeral.