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Bye Bye Love - Introduction
N ote that you will not be able to do this quest after you finish “How Little We Know", especially if you get Cachino killed in the process. On the bright side, finishing “Bye Bye Love" opens up “How Little We Know" by spawning Cachino and pointing you toward him, so you should be ableto progress normally.
You can get this by talking to either Joana or Carlitos. Carlitos is hiding in Vault 21, usually in the recreation area or the diner behind it. He's dressed as a caravaner. You will need to pass a Speech check to get him to tell you his problems though. Joana is in the courtyard at Gomorrah. You can get to it by going through the double doors in Brimstone. She should either be standing by the entrance or be dancing over in the little alcove to the right. She also has a room above that alcove. You will either need to have 50 points in Medicine or 75 points in Speech to get her to open up about her problems.
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Bye Bye Love - Love Letters
Regardless of who you talk to, the first mission will be simple. You need to find their partner and tell them that they're alive. Just go to the other and pass on the good news. Note that you can request caps for your messenger service, so mercenary players should definitely take advantage of the opportunity.
Tell each of the parties that the other is alive, and then pass on the fact that Carlitos is ready to leave the strip and Joana wants to escape from Gomorrah. Once that's settled, Carlitos should come up with a plan. He wants you to escort Joana and her girls out in disguise and take them to the rally point in Freeside, where he'll be waiting.
You can hire a few mercenaries to help out. If you even remotely think that it will come to a fight, go to the Atomic Wrangler and tell Big Beard that Carlitos is calling in his favor. They'll be ready at the rally point when the time comes. They may not help that much, but they're two expendable bodies to shield the rest.
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Bye Bye Love - Joana's Escape
Talk to Joana after midnight to signal that you're ready for the escape. She'll change into her disguise and walk out to the area right before the lobby. Two other unnamed girls will also meet her. Just run over there and try to pickpocket thugs while you wait (or find some other way to kill time). Once Joana walks over there, tell her that you're ready to make your escape. No one will stop you, so just follow them outside and down to the gate to Freeside.
Carlitos and the hired guns will be waiting on the street to the right. Save before you approach him. Once you approach him, he'll thank you, but then realize that a group of Omertas are coming in for an ambush.
If you have nine points in Strength you can carry out both intimidation options and scare off the thugs. If you have 85 points in Speech, you can convince them that you're on their side or otherwise talk them into leaving. This is also a two-level check.
You can also just fight them. Two of them will have SMGs and another two should have revolvers. The two closest should use their knives. Obviously this is a little tricky to plan out. The men with the revolvers may change to knives and enough the gunners may decide to just rush you. Be ready for close and chaotic combat.
Use a good close range weapon and use VATS to clear out the men in front of you. Rush the two gunners and draw their fire to keep Carlitos and Joana alive. If either of them dies, you will fail the quest. Once the last Omerta dies, you can talk to Carlitos to get some money (and potentially talk him into paying double with 65 points in Barter). Joana will also thank you and start up “How Little We Know" by mentioning Carlitos' side business.