Have you seen her? The redhead of my dreams?”— Jack
|Side Quest: Young Hearts|
|Talk to Jack at the Nellis hangars. (requires a  Speech check, Confirmed Bachelor perk or the Black Widow perk)|
|Travel to the Crimson Caravan Company.|
|Talk to Janet.|
|Lie to her.||Travel back to Nellis Air Force Base and talk to Pearl.|
|Talk to Jack again.|
|Return to the Crimson Caravan Company and ask Janet to put on the Boomers' outfit.|
|Talk to Alice McLafferty for Janet. (Requires  Speech or  Barter)|
|Talk to Janet.|
|Return back to the Nellis Air Force Base and talk to Janet or Jack.|
|Reward: 300 XP|
1 10mm SMG OR 470 caps
To begin the quest the Courier must talk to Jack and make a 35 Speech check. The quest can also begin with the Confirmed Bachelor or Black Widow perk. Jack reveals that he's in love with Janet, a Crimson Caravan employee he has never met. The Courier agrees to speak to Janet at the Crimson Caravan Company, which is east of both Freeside gates. Speaking to her reveals that she has seen Jack from afar and that she is interested in him. If you have the Black Widow perk there is an option to make her jealous and want to rush over. However she can't enter the Boomers' territory without attracting their fire. Lady Killer makes her admit she's dying to meet Jack. You can tell her you'll ask Pearl for permission, or...
QUEST FAILURE: You may lie with a 55 Speech check telling her that she's expected, and it's safe to approach Nellis Air Force Base. Doing so will fail the quest, and you will earn negative Karma. This will result in Janet's death as she attempts to approach Nellis AFB. If you're near Nellis while Janet is trying to approach the base, you can hear the Boomers firing at her. They will only stop when she's dead.
At Nellis AFB, convince Pearl to allow Janet entry into Nellis. A Speech check of 50 garners Janet "a free pass to enter." Without the Speech check, the quest will play out the same using the normal dialogue options. If you don't have enough Speech skill, you must complete the quest Ant Misbehavin' first before you can convince Pearl.
Return to Jack at the Hangar. He'll give you Janet's Boomer outfit (a weightless quest item) and ask you to deliver it to her. Return to Crimson Caravan and give Janet the Boomer outfit. Once again, you may lie to Janet with a 50 Speech check and tell her she has safe passage without the suit, resulting in her death, failure of the quest, and negative Karma.
Janet will then ask you to speak with her boss, Alice McLafferty, about releasing Janet from her work contract. Alice agrees to let Janet go, but she forfeits her wages as penalty for breaking the contract. With Barter 65 or Speech 75 you may convince Alice to pay Janet what she owes while letting her out of her contract. If your Barter or Speech is insufficient, you can still accept the deal and Janet is set free, without pay. Return to Janet to give her the good news; she'll immediately bolt for Nellis AFB, where you need to meet her. If you previously killed Alice during Heartache by the Number, Janet will remark on her former employer being deceased thus negating her contract and head straight for Nellis AFB.
As long as Janet has the Boomer outfit you gave her, all you need to do is meet her at Nellis. After a couple of fast-travels and/or waiting, Janet will run through Nellis AFB's front gate. Speak to her at the gate or at the hangar, and then speak with Jack to conclude the quest. The reward is 300 XP.
- If the Courier has a good reputation with Crimson Caravan Company, but they're all hostile for some reason (the player got caught stealing, etc.), try waiting for 3+ days in an area that is fairly far away.
- If the Courier's reputation with NCR is Vilified (which also affects the Crimson Caravan Company), everyone in the area becomes hostile preventing him/her from speaking with Janet.
- If the Courier is vilified by Caesar's Legion, it is possible that a Legionary assassin will kill Janet, causing the quest to fail.
- Jack and Janet may be a reference to Jack Tripper and Janet Wood from the TV show Three's Company.
- xbox360 Sometimes, when talking to Janet, the game freezes. [verified]
- pc ps3 xbox360 If you accept this quest but don't work on it, but in the meantime complete the quest Volare!, and talk to Janet for this quest, it is possible to return to Nellis and not be able to find Jack, but have a quest marker pointing to a spot in the hangar with the new B-29 bomber. Jack is actually 'stuck' in the old hangar with the broken B-29 pieces, and can only be reached by using player.moveto 000ff268. After you move to him, you can follow him outside of the hangar. He will then re-enter into the new hangar. [verified]
- xbox360 If you accept this quest and continue with Boomer missions, but do not follow up on this unmarked quest, Janet will not appear. Jack nor McCaffrey will no longer have the dialogues to support the quest. The quest will appear closed but unchecked in the PipBoy menu. This is as of the latest patch 12-10. [verified]
- pc ps3 Sometimes after initiating this quest and fast traveling out of Nellis AFB, Jack (and Loyal) will completely disappear and you will be unable to complete the quest without the use of console commands. Try player.moveto 000ff268 to move to Jack's location, which respawned him and Loyal. [verified]
- pc ps3 xbox360 After speaking with Alice about releasing Janet's contract, Janet will begin to run towards Nellis AFB, where the quest directs you to speak with Jack again. If you fast travel to Nellis AFB to speak with Jack, he will not be there. Or if you wait for Janet to reach Jack after fast traveling, he will not be in the hangar. Check the quest and have it show the location; the marker will be southeast or northwest of HELIOS One. It seems they are teleported to a coordinate based on a moving algorithm. Head to this area, and you will find Jack and Janet talking. You can speak to Jack and complete the quest, even though they are not at the base. Be prepared to defend Jack from any nearby hostiles, which he will attack and or flee from. In either case you will not be able to speak with him and end the quest, or if he dies you will not be able to end the quest. After completion they will begin walking towards Nellis AFB or they will be stuck inside a Cactus, but it's unknown if they survive the walk. [verified]
- ps3 xbox360 After speaking with Alice about releasing Janet's contract, Janet will begin to run towards Nellis AFB, where the quest directs you to speak with Jack again. If you fast travel to Nellis AFB to speak with Jack, he will not be there. Instead, both he and Janet will move to a hill near Black Mountain and HELIOS One. The hill that they stand on is entirely out of reach of the player, and you will be unable to complete the quest without the use of console commands. It is still possible to end the quest by shooting them from a distance, but impossible to complete successfully. [verified]
- pc If the above situation happens and they are at Black Mountain, thus inaccessible. They were up near the satellite dishes and using player.moveto 000ff268 then was able to complete it. [verified]
- xbox360 If you start this quest then finish Volare!, Jack and Loyal will not be at Nellis AFB after talking with Pearl. The map marker will point to Black Mountain near one of the satellite dishes. When traveling with Cass, she ran into the rock face at this spot as well and had to fast travel away before she reappeared. [verified]
- xbox360 Sometimes, after you give the Boomer outfit to Janet, and she starts running towards Nellis, if you fast travel to Nellis AFB, you will arrive before Janet does, and Janet will die before reaching you. It turns out that Janet meets a physics glitch when running through a ruined building and is launched up into the sky, then is killed when she lands. This can be avoided by standing on the spot that causes Janet to glitch, forcing her to move around the player. [verified]
- ps3 xbox360 If the player has obtained Cass as companion, and done Cass´s Heartache by the Number quest the hard way (killed Van Graff and McLafferty) Jack might not be at Nellis AFB at all. [verified]
- pc Sometimes the boomer outfit is not added to your inventory. This completes Jack's quest requirements, however, this leaves you only two options, lie (negative Karma) or end conversation. This can be fixed in the console by the player.additem 00107AF3 1. [verified]
- xbox360 If you fast travel to Nellis AFB after speaking to Alice McLafferty about the contract, Janet will be stuck hovering over the railroad tracks outside of Nellis. She acknowledges the player, however you cannot initiate conversation with her. This can be fixed by fast travelling again to the Nellis hangars (at which point, the portion of the quest regarding meeting her there will be completed. You can then speak to Jack in the Hangars and successfully complete the quest). Or save and restart the entire game then, after reloading, Janet will be with Jack.[verified]