Cassandra is worried about a prophecy involving her kissing Icarus, surrounded by gods and goddesses. Hercules promises to do what he can, but when his efforts to stop Icarus only arouse his emotions further, Cassandra instead makes a deal with Hades (who wants to know his future regarding Aphrodite and him dating) for her soul on weekends once he has successfully stopped Icarus from kissing her. To do this, Hades sends Pain and Panic, plus a new ally, Doubt; Hercules meanwhile appeals to Aphrodite, goddess of love, who gives him arrows to shoot at Cassandra to make her fall in love with Icarus. Unfortunately, Icarus is struck with doubt, causing mayhem until the two both wake up and Hades puts him in an eternal sleep, and Cassandra must kiss him to wake him. Aphrodite rejects Hades' advances, reminding him of her fiancee, Hephaestus, with whom Hades has an unpleasant confrontation.
- Tate Donovan as Hercules
- French Stewart as Icarus
- Sandra Bernhard as Cassandra
- James Woods as Hades
- Lisa Kudrow as Aphrodite
- Bobcat Goldthwait as Pain
- Matt Frewer as Panic
- Cassandra and Icarus share their first kiss in this episode.
- It's revealed that Hades has a crush on Aphrodite, but she rejects his feelings and is engaged to Hephaestus.
- This episode begins the running gag where Hephaestus attacks Hades in a jealous and angry rage whenever he flirts with Aphrodite.