New Vegas Strip, North

Head to Gomorrah, located on the western side of the New Vegas Strip, across from the Lucky 38. Your weapons will be confiscated upon entry; ensure you keep any holdout weapons.

Talk to the Receptionist and ask for gossip. Pass a [Speech 28] check to learn about events on the Strip.

Proceed north-west through the casino to the casino floor.

Continue north-west to find three doors. Enter the southern-most door on the north-western end of the casino.

Go through another doorway to the north-east, then find doors to the north-west that lead to the Courtyard.

Upon arriving in the courtyard, you will meet Joana. You can pass a [Speech 50] check, followed by a [Speech 75] check, to be invited to her room. Alternatively, you can choose to ask her questions, leading to a [Medicine 50] check.

In her room, continue the conversation about her problems, which can be advanced with another [Speech 75] check or the [Medicine 50] check. For maximum XP, pass both Speech checks and the Medicine check.

After she shares her problems, ask her about Cachino, Carlitos, and the Omertas. This initiates the quest Bye Bye Love and provides information about the Omertas.

For helping find Carlitos, Joana will offer 200 Caps or sex upfront.

You can also speak with Dazzle, another prostitute, for 100 Caps (50 Caps with the [Black Widow] perk).

Leave Gomorrah and go to the southern end of the New Vegas Strip to enter the Vault 21 Gift Shop.

Go through a door to the west, descend stairs, and pass through more doors to reach Vault 21.

Find Carlitos within Vault 21 and inform him about Joana. He will agree to help her escape if you do the work, offering to do it for 200 Caps or for free.

Ask Carlitos questions about Gomorrah, himself, and points of interest in New Vegas. Pass an [Intelligence 7] check to gain extra information and XP.

Return to Gomorrah and report to Joana about Carlitos.

Pass a [Speech 40] check to prevent Joana from wavering about leaving, then pass a [Speech 50] check to give her a plan to avoid the Omertas.

Visit Carlitos back at Vault 21 to finalize the escape plan.

To recruit optional backup, go to the Atomic Wrangler in Freeside and speak with Big Beard near the stage. Tell him Carlitos is “ready to cash in his chips.”

Travel to outside Gomorrah and wait until midnight. Return to Joana and initiate the escape.

Leave Gomorrah with Joana and two Disguised Hookers towards the meeting spot.

At the meeting spot, Carlitos and potentially the hired Beards will meet you. Four Omerta Thugs will appear. You can attempt to resolve this peacefully by passing a [Speech 75] and a [Speech 85] check, a [Barter 85] check to pay them 500 Caps, or a [Strength 8] check to intimidate them. Failing these will result in combat.