Young Hearts

A matchmaking quest. You find Jack at Nellis Hangars; he is in love with a redhead named Janet. She's found with the Crimson Caravan Company, east of Freeside. Janet will tell you she return's Jack's feelings but worries about how to get into the Boomers' compound. You can tell her you'll ask Pearl for permission, meaning you'll have to return to Pearl's Barracks to do a little convincing.

Alternately, you can take the evil path, lie with a 55 speech check, and tell her that the coast is clear. This would presumably yield a karma-losing though amusing outcome which the player could witness.

Convince Pearl to allow Janet entry into Nellis. A speech check of 50 garners Janet "a free pass to enter"... although it remains unclear exactly how this speech check shortcuts the task, or otherwise alters the quest's procedure/outcome.

Return to Jack at the Hangar. He'll give you a Boomers outfit and ask you to bring it to Janet. Return to the Crimson Caravan and tell Janet she's clear to enter. She'll then ask you to speak with The boss Alice McLafferty, you'll need to convince her (Barter 65, Speech 75) to pay Janet what she owes and and let Janet out of her contract. Then you'll go back and speak with Janet let her know the outcome and give her the boomer outfit. Now you need to meet her back at the base, this can be a bit tricky, I suggest fast traveling to Fields Shack just southeast of the base. Once you get the the shack, Janet will be running her way from the crimson caravan, catch her and run with her all the way to the gate of the base, otherwise without you being there the base will fire on her and kill her. Once your through the gate the mission is successful, just meet back up with Jack and the quest will be completed.