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Background

When you talk to Jack in the hangar at Nellis Air Force Base, he'll mention a personal matter that you could help him with, but he'll only tell you about it (and trigger the quest) if you have Speech 35, the Black Widow perk, or the Confirmed Bachelor perk.


Walkthrough

When you convince Jack to talk, he'll tell you that he's spotted "the most beautiful woman who ever lived" at the Crimson Caravan Company, and that he think she's noticed him, too. Jack won't be able to tell you much about her, only that she has short red hair, but since you're allowed to leave the base, he'll ask you to seek her out.

You'll find the girl, Janet, in the brahmin pen at the Crimson Caravan Company. When you talk to her there, she'll verify that she's seen Jack, and that she's interested in him, too. If you're feeling devious, and if you can beat a Speech 55 check, then at any time during the quest, you can lie to Janet and tell her that she's expected at Nellis, which will cause her to rush right over and get killed by the artillery fire. This will cost you karma and also fail the quest.

Assuming that you actually want to help Jack and Janet, then next up you'll need to talk to Mother Pearl at Nellis Air Force Base. No matter what you say to her, she'll agree to allow Janet to enter the base. When you return with this news to Jack, he'll give you a Boomer Outfit for Janet so she can enter the base safely.

However, when you give the outfit to Janet, she'll mention that if she leaves now, then she'll lose her unpaid wages, and so she'll ask you to negotiate a deal with her boss, Alice McLafferty. You'll find McLafferty in the main office at the Crimson Caravan Company. With Speech 75 or Barter 65, you'll be able to get Janet her wages (which will earn you some extra Boomer fame). Otherwise you won't. But either way, when you return to Janet, she'll start her trek to Nellis Air Force Base.

Note: If McLafferty is dead, then Janet won't worry about her wages at all, and she'll just head to Nellis Air Force Base.

To complete the quest, you'll just need to wait for Janet to reach the hangar at Nellis Air Force Base (this might require you to wait for a couple of hours), and then you'll need to talk to Jack. For your efforts, you'll receive 300 xp and some Boomer fame.