In Book of the Damned, the Trucker Cupid is in a diner when Castiel and a now-human Metatron are eating. Spotting them as they head to the bathroom due to Metatron being lactose intolerant, the Cupid waits outside by Castiel's car for them. When they emerge, the Cupid greets the two who are surprised by his recognition and he explains that he is just "an angry, angry Cupid." The Cupid draws an angel blade, intending to kill the two for corrupting Heaven and engages in a fight with Castiel. Though Castiel is stronger, the Cupid knocks him to the ground long enough to go after Metatron who is hindered by a leg wound given to him by Sam Winchester. Castiel manages to tackle the Cupid off of Metatron, but loses his own angel blade in the process. The Cupid takes advantage of this to pin Castiel to the ground and struggles to kill Castiel with his angel blade. Before either can overpower the other, Metatron retrieves Castiel's angel blade and stabs the Trucker Cupid through the back with it, killing him. Following the fight, Castiel takes the Cupid's angel blade and tells Metatron that his actions change nothing between them.
- Angel Blades - He was killed by an angel blade.