Jake's school was going on a Valentine's day "love cruise". Jake was planning to go with Rose, while Trixie had her sights set on her long time crush, Kyle Wilkins. Spud, as usual, was hoping to go with Stacey. A few days before the cruise, however, Grandpa approached Rose and asked her to break up with Jake, as Jake could not focus on anything except Rose and it was interfering with his dragon training and possibly endangered him.
Meanwhile, Cupid, who was taking a break came by the shop and dropped off his bow and arrows. Rose found Jake and tried to tell him that she had to end their relationship, but Jake didn't understand. Jake decided to take Cupid's bow and arrows to make Rose fall in love with him again, as well as set up Spud and Trixie with their on crushes. On the cruise, he first tried to test the bow on Rotwood, but missed and hit the boat's captain, who fell madly in love with the Statue of Liberty.
Jake tripped and spilled arrows over a crowd of people, causing them to fall in love at random. Jake seeked out Rose and shot her with an arrow, but as Rose was still in love with Jake, being forced to break up with him for his own safety, the arrow's effect was reversed and Rose once more attempted to slay Jake so they engaged in a battle, with Jake escaping.
Rose going so far as to tell the Huntsman Jake's name, though it was blocked by two claps of thunder. Rose called in the Hunstsclan, who attempted to kill Jake. At the last second, Jake got an arrow into Rose and she lead the Huntsclan away. She explained that she had to break up with him for his own safety, and left. Jake took the bow and restored everything back to has it was. Cupid came by the shop two weeks later, explained to Jake that love cannot be messed with. He gave Jake some chocolate and "heartbreak cream".
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