Hercules and the Big Kiss

Hercules and the Big Kiss is an episode of Hercules: The Animated Series. It premiered on September 11, 1998

Summary
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, who Hades has an unpleasant confrontation with.