Bye Bye Love

Bye Bye Love is a side quest in Fallout: New Vegas.

Synopsis
Joana wants to leave her life at Gomorrah behind her and wants to escape into the arms of her lover Carlitos.

Walkthrough

 * 1) Talk to Joana; a Medicine check of 50 or Speech of 75 is required to get her to talk about Cachino or Carlitos. Alternatively, talk to Carlitos directly in Vault 21.
 * 2) Run messages between Joana and Carlitos.
 * 3) (Optional) Hire Big Beard and Little Beard at the Atomic Wrangler Casino to escort the two lovers.
 * 4) Speak to Joana  between 12:00 and 6:00 AM and help her and some other prostitutes escape.
 * 5) Deal with the Omerta thugs stopping their escape.
 * 6) Kill them or convince them to leave with two Strength checks at 8 and 9, or two Speech checks at 75 and 85.

Behind the scenes
The name of the quest is a reference to The Everly Brothers 1957 song of the same name.

Bugs

 * Carlitos and Joana won't appear in the game, if you have advanced far enough in the quest How Little We Know even after you started conversation with both, making the quest impossible to complete.
 * To fix this on PC, use the following console commands: For Carlitos:, , . For Joana: , , while standing in the courtyard.
 * The downside of this method is that once you have to escort her and the disguised hookers out of Gomorrah, they may not move. A solution to this is to start combat with Joana, leave Gomorrah, then go back in and restart dialogue with her. After that, exit Gomorrah, enter Freeside, and Joana and the disguised hookers should appear next to you resuming the quest.
 * Once the group reaches Freeside, the thugs that are supposed to interrupt the escape, sometimes won't appear. This can be bypassed by using the console command and talking first to Carlitos once (before or after the command), then to Joana.
 * After escorting Joana and the disguised hookers to Freeside, Carlitos might not appear making the quest incompletable when Joana, the disguised hookers, and the Omerta thugs stand around and do nothing. Killing the Omerta thugs won't work since Joana and the disguised hookers still need Carlitos to appear to advance the quest dialogue. Reloading the auto-save from when you entered Freeside can fix this.
 * When leading Joana and the disguised hookers outside the gate to Freeside, the Securitrons posted outside the gate can become hostile, attacking all included people. Killing them gives infamy for the Strip but letting them kill Joana fails the quest.
 * After running back and forth a few times the dialogue option to get Joana to run away might fail to appear; you will need to have a high enough speech skill to convince her.