Though beloved members of our heroic crew, sometimes officers Clare President (Taylor Moore) and Rip Van Winkle (Tim Platt) can feel like outsiders. And when the ship's hot new schoolmaster, Ichabod Crane (Branson Reese) threatens Rip's status as "Ship's Public Domain Washington Irving Character Brought to Life", he starts to wonder, do I belong here at all? Even Clare seems to love him! No one even cares that Ichabod slept with Rip's wife like 700 years ago! Maybe the only thing that can keep him is an important lesson... of friendship.