Bye Bye Love

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

Detailed walkthrough
NOTE: It seems that there is no way to complete this quest without passing a 50 speech check.

This is a quest that begins in either the Gomorrah casino and hotel or the Vault 21 hotel. If the Courier goes into the Gomorrah courtyard, Joana will begin a conversation. Passing a Medicine (50) or Speech (75) check will initiate dialog that will eventually have Joana talk about Cachino and Carlitos. She will offer the player 200 caps or sexual services for taking the quest (the second option is only available if your character is male, or a female with the Cherchez La Femme perk). Or the player can talk to Carlitos in Vault 21, pass a speech check about why he left the Omertas and Joana. Carlitos will give the player 200 caps upon accepting the offer to help him and another 200 upon completion.

The player has the option to help Joana, before or after choosing to have a sexual encounter, by finding Carlitos (located in the diner of Vault 21) or letting her know Carlitos is looking for her. After some running back and forth between Joana and Carlitos, the player can agree to help Joana, and two of her fellow prosititutes escape to Freeside to join Carlitos; the agreement being to wait until between 12AM and dawn, being Gomorrah's most busy hours, before attempting the escape. Carlitos advises the player to get some backup before attempting the escape, as he knows two guns-for-hire that owe him a favor. This gives the Courier the option to recruit Big Beard and Little Beard who are located in the Atomic Wrangler Casino. Talking to a disguised Joana in the lobby triggers the escape itself and is literally just walking the disguised girls from the Gomorrah lobby through the front doors of the casino and out of The Strip. However, always let them pass through the doors and gates first as not doing so may result in the quest failing for leaving the girls behind.

Once you meet up with the hired guns and Carlitos, 4 or 5 Omerta thugs will ambush the group. The player can either go into combat with them or with high enough Strength (8,9) or speech (75 and 85) skill, avoid the fight altogether. Carlitos and Joana must survive the confrontation or else the quest will fail. If successful Carlitos will thank the player and ask if there is a way to repay the kindness. From here you have a choice between receiving 200 caps or accepting a simple thanks. Alternatively, if you talked to Carlitos first and you have a high enough Barter skill (65), you can get another 400 caps on top of the 200 at the start.

From here Joana will thank the Courier and mention a sinister plot she's heard about from Cachino about the Omertas. The How Little We Know quest will initiate if you haven't found this quest already.

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.
 * After running back and forth a few times the dialogue option to get Joana to run away might fail to appear, you'll need to have a high enough speech skill to convince her.
 * 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.
 * When Joana and the disguised hookers are waiting in the Gomorrah lobby the game can crash when exiting the strip, avoid this by allowing all four of them to leave first.
 * After escorting Joana and the disguised hookers to Freeside; Carlitos might not appear making the quest un-completable 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.
 * Once the group reaches Freeside, the thugs that are supposed to interrupt the escape, sometimes won't appear.

Behind the Scenes

 * The name of the quest is a reference to The Everly Brothers song of the same name.

Прощай, любовь