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Young Hearts - Introduction
Once you make it to the Boomers HQ at Nellis Air Force Base (which deserves its own article), you'll need to gain the favor of the Boomers. This isolated community needs a lot of help. One great option for a lot of favor involves the quest "Young Hearts." You can get this quest by finding Jack. He's usually inside the main terminal, and he should be marked with a quest marker.
Talk to him and you should be able to get him to open up if you're Speech is above 35. He'll mention that he's in love with a red-haired woman at the Crimson Caravan compound, who he has only ever seen through his binoculars while on watch. Agree to help him out to start the quest.
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Young Hearts - Matchmaking or Breaking Hearts
She actually knew about Jack's appreciation and likes him too. Now, if you're feeling cruel and have 55 points in Speech you can lie and tell her that Jack's already waiting for her at the Boomer Base and that she's free to go now. She'll run off and be blown apart by their artillery fire. Probably one of their more cruel things that you can do in the game.
If you want to help them get together, go back to Nellis Air Force Base. You can talk to Pearl and get her permission for the invitation. This actually doesn't seem to impact anything, other than being a bit more "proper" for the overall quest. The main thing is to talk to Jack. He'll give you a spare Boomer jacket to give to Janet. This will mark her as a friendly and they won't fire at her when she comes.
Deliver the jacket to Janet, only to find out that she can't get out of her contract with the Crimson Caravan. There are a few ways out of this.
If worse comes to worse, you can just tell her that she'll have to forfeit the wages owed. She'll accept it, but it's not ideal.
You should be able to get Alice McLafferty to let her out of the contract with either 65 points in Barter or 75 points in Speech. If you're doing the violent side of "Heartache by the Number" then you can just kill her. Janet will note that her contract was negated by Alice's death, so she'll leave normally.
Regardless of how you get her to leave the company, she'll take off for Nellis Air Force Base after your conversation. After a day or two, she should be in the hangar with Jack. Just talk to either of them to complete the quest or a lot of reputation with the Boomers and a fair bit of XP.