|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.|
|Talk to Janet.|
|Lie to her.||Travel back to the Nellis Air Force Base and talk to Pearl.|
|Talk to Jack again.|
|Return to the Crimson Caravan 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|
10mm SMG -OR- 470 caps
At the Nellis Air Force Base, a man named Jack can be spoken to, and with a successful 35 Speech check, the Confirmed Bachelor perk, or Black Widow perk, Jack reveals that he is in love with a girl named Janet, a Crimson Caravan employee he has never actually met. The Courier can agree to speak to Janet at her place of work, 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. With the Black Widow perk, there is an option to make her jealous and want to rush over, while with the Lady Killer perk, she will admit that she's dying to meet Jack. The Courier can tell her that they'll ask Pearl for permission.
To get Janet into Nellis, when speaking to Pearl, a successful Speech check of 50 garners Janet "a free pass to enter." Failing the check, the Courier must first complete the quest Ant Misbehavin' in order to be able to convince Pearl.
Return to Jack at the hangar, and he'll hand over Janet's Boomer outfit, and ask to have it delivered to her. Return to Crimson Caravan and give Janet the Boomer outfit, in which she will then ask for the Courier 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 a penalty for breaking the contract; however, with a skill check of Barter 65 or Speech 75, Alice can be convinced to pay Janet what she owes while also letting her out of her contract. Return to Janet to give her the good news, and she will immediately leave for Nellis, in which Jack will need to be spoken to again to conclude the quest, and receive a reward of 300 XP.
- If the Courier previously killed Alice during Heartache by the Number, Janet will remark on her former employer being deceased, thus negating her contract with the company.
- Janet can be lied to with a successful 55 Speech check, telling her that she is expected at the base and that it's safe to go to Jack before arranging for her to do so safely. Doing so will fail the quest, earning negative Karma and resulting in Janet's death as she attempts to approach Nellis. Failing the check results in her knowing that she is being lied to, asking if they are trying to get her killed, and will also fail the quest.
- If Janet was killed by the bombardment, Jack can always be found sleeping at the Nellis workshop afterward. When talked to, he will be furious and ask why the Courier did not stop her. After being lied to with a 35 Speech check that she risked everything for him, he will "Curse the walls of Nellis" and go back to sleep. If the check was failed or respond its not the player character's fault she's dead, he will refuse to speak with the Courier.
- Xbox 360 Sometimes, when talking to Janet, the game freezes. [verified]
- PC If the quest was failed by getting Janet killed trying to enter Nellis, the dialogue for Jack being upset over it will never trigger. He will always be sleeping at the Nellis Workshop and his default dialogue will still show.[verification needed]
- A third-party fix for this bug is included as part of Yukichigai's Unofficial Patch.
- PC Playstation 3 Xbox 360 If accepting 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 moving to him, one can follow him outside of the hangar. He will then re-enter into the new hangar. [verified]
- Xbox 360 If this quest is accepted and continue with Boomer missions, but do not follow up on this unmarked quest, Janet will not appear. Jack nor McLafferty will no longer have the dialogues to support the quest. The quest will appear closed but unchecked in the Pip Boy menu. This is as of the latest patch 12-10. [verified]
- PC Playstation 3 Sometimes after initiating this quest and fast traveling out of Nellis AFB, Jack (and Loyal) will completely disappear and one 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 Playstation 3 Xbox 360 After speaking with Alice about releasing Janet's contract, Janet will begin to run towards Nellis AFB, where the quest directs to speak with Jack again. If fast traveling to Nellis AFB to speak with Jack, he will not be there. Or if one waits 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 the Courier will find Jack and Janet talking. One 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 the player character will not be able to speak with him and end the quest, or if he dies one 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]
- Playstation 3 Xbox 360 After speaking with Alice about releasing Janet's contract, Janet will begin to run towards Nellis AFB, where the quest directs to speak with Jack again. If fast traveling 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 they 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]
- Xbox 360 If the Courier starts 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]
- Xbox 360 Sometimes, after giving the Boomer outfit to Janet, and she starts running towards Nellis, if fast traveling to Nellis AFB, the Courier will arrive before Janet does, and Janet will die before reaching the Courier. 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 character. [verified]
- Playstation 3 Xbox 360 If the player character 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 the inventory. This completes Jack's quest requirements, however, this leaves only two options, lie (negative Karma) or end conversation. This can be fixed in the console by the player.additem 00107AF3 1. [verified]
- Xbox 360 If fast traveling 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 character, however one 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. The Courier 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]