Role in the series
The Ruby Heart of Hearts first appeared in the episode "Hooked!" where Red Jessica joins Captain Hook on a treasure hunt for the Ruby Heart of Hearts. Seeing his chance to make a good impression on his beloved pirate gal, Hook orders his crew to stay behind while Hook and Jessica search for the ruby. While in search for the treasure Hook faces many obstacles on the trail but unknown to him Jake and his crew worked behind the scenes to help Hook reach the Ruby Heart of Hearts with Red Jessica.
Hook and Jessica finally made it to the Ruby Heart of Hearts but the trail crumbled under their feet, leaving a gorge between the two pirates while Red Jessica headed back to her ship. Captain Hook refused to give up, muscling enough courage to attempt to retrieve the treasure. The floor gave way, sending Hook falling to his doom until the captain is recused by Izzy and her pixie dust, allowing Hook to fly over the gorge and retrieving the treasure for Red Jessica.