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, you have three options: attack the squatters, pay them off using Barter skill check, or threaten them into leaving using Speech skill check. Once that is done, return to Crandon.

Crandon will be impressed with your work, and assign you 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. You can immediately attack him, or else pass a level 65 Speech skill check in which case he will stop causing trouble. If your Speech skill isn't high enough, you can use Barter (level 50 required) to pay him 50 caps to stop. Otherwise, your last option is to 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 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. Enter The Gray, and search for Andy and Alice's whereabouts. Once inside, you must search for clues as to where they have left. To do so, you must enter Andy's locked room (Lockpick level 50 required), which is guarded by a Thug. If you have Speech skill of 70, you can lie to him and he will leave his post. Otherwise, you may have to kill him. (Addition: Sometimes he leaves his post with a woman - I was able to get in and out with no problems. Haven't met with ghoul Andy either. This was before dealing with Greasers, maybe that's why). Once you are in the room, pick up the Henchman Message to Andy Scabb underneath the TV. As you leave, you will be confronted by the ghoul Andy.
 * When I tackled this quest, the thug went on a patrol route after a little while (and there was a female "North Vegas Resident" in the room), so you can do this without violence if you're patient. I personally did a sneak-silenced kill on him after passing the speech check... so I could loot his body.

After dealing with Andy, it will ask you to go back to the Hostetler house to report back to the mother, but when you enter you will be approached by Alice who is very upset, to be able to talk her into listing to you your speech has to be over 70, but you do not need an intelligence of 7 to convince her to not kill her mother. 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 is not high enough she will kill her mother and father, ending the quest.

Behind the Scenes
"Someone to Watch Over Me" is a song made by Frank Sinatra.

Bugs

 * 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.
 * 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.

Videos
VtQHyyJQrG4