Cry Me a River

 is a side quest in Fallout: New Vegas.

Quick walkthrough
Jerry the Punk at Red Rock Canyon is unhappy about his Great Khan initiation. He wants you to see if the Followers of the Apocalypse in Freeside will let him join.

Detailed walkthrough
Jerry the Punk can be found by the fenced area west of the entrance to Red Rock Canyon. With a Speech check of 33, he tells the player he doesn't really wish to be a Khan and finds far more satisfaction reading poetry. He wants to be somewhere where poetry is appreciated and asks the Courier to speak to the Followers of the Apocalypse on his behalf. Speak with Julie Farkas at the Old Mormon Fort about Jerry wishing to join. After she accepts, travel back to Jerry and tell him the good news.

Bugs

 * Sometimes Jerry and two other Great Khans become hostile when you come back with the good news.
 * Jerry's pathfinding causes him to sometimes pace in the dueling ring; this unfortunately causes him to walk right past the Khans attacking the practice dummies. He will subsequently be killed and the quest will fail. Upon the player's return with permission for him to join the Followers, he may still be killed in this fashion, thereby rendering the quest impossible to complete if stuck in this recurring death loop. Jerry can be protected long enough to complete the quest by reverse pickpocketing stronger armor into his inventory. Even if he dies and after accepting the quest, Julie Farkas will still have all associated quest options in her dialog tree.
 * After completing the quest, Jerry will sometimes be at his hut in Red Rock Canyon instead of being in the Old Mormon Fort.

Behind the Scenes

 * "Cry Me a River" is a popular American torch song (sentimental love song), written by Arthur Hamilton and first performed by Julie London.
 * The phrase "cry me a river" is a colloquial sarcasm in response to someone who is perceived to be making unreasonable or excessive complaints.