Jake's school is going on a Valentine's Day "love cruise". Jake is planning to go with Rose, while Trixie has her sights set on her long-time crush, Kyle Wilkins. Spud, as usual, is hoping to go with Stacey. A few days before the cruise, however, Grandpa approaches Rose and asks her to break up with Jake, as Jake cannot focus on anything except Rose and it is interfering with his dragon training and possibly endangering him, saying that they should keep their relationship strictly professional. Meanwhile, Cupid, who is taking a break comes by the shop and drops of his bow and arrows. Rose finds Jake and tries to tell him that she has to end their strong and close romantic relationship, but Jake doesn't understand. Jake decides 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 romantic crushes.
On the cruise, he first tries to test the bow on Rotwood, but misses and hits the boat's captain, who falls madly in love with the Statue of Liberty. Jake trips and spills arrows over a crowd of people, causing them to fall in love at random. Jake seeks out Rose and shoots her with an arrow, but as Rose is still in love with Jake, being forced to break up with him for his own safety, the arrow's effect is reversed, and Rose once more attempts to slay Jake, going so far as to tell the Huntsman Jake's name, though it is blocked by two claps of thunder. Rose calls in the Hunstsclan, who attempts to kill Jake. At the last second, Jake gets an arrow into Rose and she leads the Huntsclan away. She explains that she had to break up with him for his own safety, and leaves. Jake takes the bow and restores everything back to has it was. Cupid comes by the shop to weeks later, explaining to Jake that romance and love cannot be messed with. He gives Jake some chocolate and "heartbreak cream".