Fallout: New Vegas/Young Hearts

This quest is received from Jack in the Nellis Air Force Base. 35 speech, or the Confirmed Bachelor or Black Widow perks, will get him to admit that he's in love with Janet, a Crimson Caravan employee he's never met.

The Quest
After initiating the quest, fast-travel to the Crimson Caravan Company. Here you will find Janet, and speaking to her will reveal that she likes him too. If you have 55 speech you can lie to her and say she's expected, and she will run to the base and get killed, failing the quest and giving you bad karma in the process.

Go back to the base and speak to Jack. He will be very happy, but express his concern about her getting to the base. He'll ask you to get permission from Pearl. You can convince her by having 55 speech or by completing the ../Ant Misbehavin'/ quest for her, at which point she will allow her a free pass. Returning to Jack will get you a Boomer costume for Janet to wear to get across the field.

Return to the Crimson Caravan Company and give the suit to Janet, who will ask you to speak to Alice McLafferty to release her from her contract. Alice will agree to do so without pay, or if you have 65 barter or 75 speech, she will agree to release her with full pay. Talk to Janet again and she will leave for the Nellis Air Force Base.

At the base, wait for Janet to turn up and watch Jack and Janet meet for the first time. Speaking to Jack will conclude the quest, gaining you 300XP.