And there will be a time of crisis, of worlds hanging in the balance. And in this time shall come the Anointed, the Master's great warrior. And the Slayer will not know him, will not stop him, and he will lead her into hell. As it is written, so it shall be. Five will die, and from their ashes the Anointed One shall rise. The Brethren of Aurelius shall greet him and usher him to his immortal destiny.
Buffy finally gets a date—sensitive hunk Owen shows an interest in her. To Giles' exasperation, all Buffy can think about is impressing him with an uncharacteristic interest in the American poet Emily Dickinson. In the school cafeteria, Buffy has to fight off Cordelia to sit at one table with Owen, but it is worth it. He asks Buffy out on a date to The Bronze that very evening.
However, Giles has found out about the prophecy from the symbol on a ring they found in the cemetery. He is convinced that the Anointed One will rise that night, and so despite Buffy's protests, they spend hours sitting on graves waiting for a vampire to rise. None does, however, and though Giles is certain that his calculations are correct, he calls their stakeless stake-out quits. Buffy rushes to The Bronze, only to see Owen dancing with Cordelia. Crushed, she leaves without trying to talk to him.
At the same time, in a bus on the way to Sunnydale, a man stands up and begins to lecture the other passengers on God's judgment, quoting prophecies. Suddenly, a vampire walks in front of the bus, causing it to crash. Other vampires swarm the wreck, attacking the passengers, including the religious man.
The next morning, Owen asks Buffy out on another date that night and even gives her a pocket-watch so that she doesn't miss it this time. Buffy jumps at the opportunity, while Xander is left to stew in his jealousy.
When evening comes, Giles shows up at Buffy's house, waving a newspaper that shows five people died when the bus crashed, among them the suspected murderer Andrew Borba, the man who was quoting prophecies. Buffy insists on going to the Bronze, though, so Giles decides to check the Sunnydale funeral home himself. Unfortunately, there are vampires present to get the Anointed One, and they trap Giles in a room. Xander and Willow have followed him, though, and run back to The Bronze to get Buffy.
There, first Cordelia, then Angel tries to come in between Buffy and Owen. Finally, Xander and Willow managed to get her to come to the funeral home by pretending to be a couple that wants to do something daring on a double date. When Buffy figures out what has happened, she tries to dump Owen, but unfortunately, he tags along. Even worse, he is present in the funeral home when Borba rises as a vampire. In the fight, Owen is knocked unconscious. Buffy, angry that he has "killed [her] date," kills Borba by sliding him into the furnace while still alive, or rather, still undead.
The next morning, Owen is extremely excited about what they have been through and wants more — this is what he likes about Buffy, he says, and almost being killed made him feel alive. She realizes that there is no way that she can have a relationship with him; sooner or later, he will get himself killed. With a heavy heart, she breaks up with him.
Giles tries to comfort her by telling her what a burden it was for him as a ten-year-old to find out his destiny was to be a watcher when he would rather have been a fighter pilot — or possibly a grocer. Both agree that at least the Master will be unhappy, too, because the Anointed One was destroyed.
But in his underground lair, the Master is overjoyed as he welcomes the real Anointed One — not Borba after all, but a young boy who was on the bus with him.
During scenes between Buffy and Owen at the Bronze, Velvet Chain is performing “Strong” and “Treason” from their album ‘’Groovy Side’’. When Cordelia and Owen dance, Three Day Wheely’s “Rotten Apple” is playing. When Angel warns Buffy about the threat, the song is “Junky Girl” by Rubber from their self-titled CD. Finally, when Buffy rejects Owen at school, the song “Let the Sun Fall Down” by Kim Richey plays in the background.
“Never Kill a Boy on the First Date” earned itself a Nielsen rating of 2.8 on its original airing. It was the 104th most watched show out of all 115 primetime shows of its time; fifth out of the eleven shows from The WB.