Someone to Watch Over Me

 is a quest in Fallout: New Vegas.

Quick walkthrough

 * Talk to Crandon at North Vegas Square, Speech skill of 45 or barter skill of 35 is required, to initiate the quest.
 * Deal with the newcomers.
 * Obtain the next assignment from Crandon.
 * Enter the north sewers through the manhole, and deal with the Greasers.
 * Return to Crandon for the next assignment.
 * Talk to Mrs. Hostetler, and help her spy on her daughter's new friends.

Detailed walkthrough
Go to North Vegas Square and talk to Crandon. Ask him if he needs any help, and he will tell you to deal with unwanted squatters that have recently come to the area. Travel to the squatters, and talk to Squatter Bill. From here, the player has three options
 * attack the squatters
 * pay them off using barter
 * threaten them into leaving using speech skill check

Once that is done, return to Crandon.

Crandon will be impressed with the work, and assign a new mission. This time, it requires dealing with a few troublemakers in the sewers. Enter the north sewers manhole. From here, follow your map marker until you reach a group of Greasers. Talk to the leader of the group, Greasy Johnny. The player has four choices:
 * attack him
 * use 65 speech to talk him out of causing trouble
 * use 50 barter to offer him 50 caps to stop
 * pay him 100 caps

Once the Greasers are dealt with, return to Crandon for the next assignment. He will tell you to see Mrs. Hostetler because her daughter is getting to know the wrong crowd of people. Follow the map marker to Hostetler Home, which is due south of Crimson Caravan Company and northwest of Durable Dunn's Sacked Caravan. Inside, talk to Mrs. Hostetler about any work needing done. She will ask you to spy on her daughter, Alice Hostetler, to see what her new friends are up to.

Travel back to North Vegas Square and speak with Jules. He will tell you she's hanging out with Andy Scabb and his crew in The Gray. Using 50 guns, the player can tell Jules he "looks like he can handle himself". Enter The Gray to search for Andy and Alice's whereabouts. Once inside the player must enter Andy's locked room, either using 50 lockpick, or a key on the Thug guarding the door; the key can be stolen or lifted off his corpse. With a speech of 70, the player can lie to him and he will leave his post, otherwise, the player can simply kill him without the surrounding NPCs turning hostile, or wait for him to leave his post voluntarily, as happens on occasion.

Once you are in Andy's room, pick up the Henchman Message to Andy Scabb underneath the TV. As you leave, you will be confronted by the ghoul Andy. The player can lie to him with 65 speech. Andy adds an optional part of the quest, which involves helping him steal the Crimson Caravan money from the Hostetlers.

After dealing with Andy, the player should return to the Hostetler house to report to the mother, but upon entering the player will be approached by Alice Hostetler who is very upset. To talk her out of attacking her mother requires 75 speech or 7 intelligence, it is also possible through the speech options to convince Alice to reconcile with her family as well. There is a second speech check of 75 that convinces Alice that only she can answer her dreams which results in good karma. Talking to Mrs. Hostetler completes the quest.

If your speech/intelligence is not high enough she will kill her mother and father, ending the quest.

When you have stopped Alice from killing her parents and made her leave, the quest will tell you to talk to Mrs. Hostetler. You can either kill her yourself, looting the 1000 caps and gaining negative karma, decline any reward and gain positive karma or get 200 or 500 caps, depending on if you demanded a reward or told her Alice would have left anyways respectively.

Behind the Scenes
"Someone to Watch Over Me" is the name of a song written by George and Ira Gershwin in for the 1926 Broadway musical Oh, Kay! Considered part of The Great American Songbook, the song has been recorded many times by many artists, including Frank Sinatra, Barbara Streisand, Stéphane Grappelli, Keely Smith, Rosemary Clooney, and Ella Fitzgerald.

"The Greasers" and "Johnny" are from the book The Outsiders by S.E. Hinton.

Bugs

 * If you have already wiped out Motor Runner and the fiends in that vault before starting this quest line you can sometimes get stuck. After getting the "squatters" to leave Crandon will only reply with "I hear you took care of the fiends around here". This can be solved by going and speaking with Jules and passing his Guns and Survival check to get the magnum ammo note then Crandon's dialog will change (but you MUST get the squatters to leave, speak to crandon, then speak to jules, then to crandon again) I was able to overcome this by simply talking to Crandon a time or two until the option to turn in the squatters was given (X360).
 * If you use the intelligence speech check to convince Alice to stay, then leave the building before talking to Mrs Hostetler, the quest will fail on the spot. Negative karma is awarded when the quest fails, even though you have just gained karma for convincing Alice not to attack her parents. On going back into the house, Alice appears dead laying over the dining room table from where she sat down after convincing her not to kill her parents. Her mother will enter through the front door of the house in a hostile state, even though Alice is already dead on the table and start shooting at the player. If you have a companion with you they will kill her, regardless, no interactions are possible at that point.
 * On PC, if you leave the building before talking to Mrs Hostetler, return to the building, reset the quest,resurrect Alice(base_id: 000f6373),then set quest stage, by that order, to 10,20,25,30,40,45,50,60. Then you must talk to Alice and can finish the quest normally.
 * There will sometimes be no speech option available, as it goes back to the Intelligence Option numerous times.
 * If experienced on the PC, you can fix it somewhat with console commands. Using the base id on this page, reset the quest, set the quest stage to 55, resurrect Alice and talk to her again. The questline will be completly bugged at this point though. The only way found to have the quest end sucessfully without the Courier being blamed for killing her was to tell her to run away.


 * It's possible, when Andy confronts the Courier, to exit conversation without a speech check or fighting by selecting the, "Goodbye" option, which, presumably, is not supposed to be available. Andy will then act as if nothing has happened and allow the Courier to continue with the quest.  It is unknown whether or not this will cause a later bug with the quest.