Jack is the second Newspaper Job assignment. He was a copywriter at the ad agency but got fired for "erratic behavior", whatever that means. He is kind of strange though. Anyways, You are tasked with going over to his apartment (Regal Apartments - middle door) to interview him.
He ends up interviewing you. He asks a bunch of thought-provoking questions. Just say what you truly believe. Your answers will choose if he decides to self-preserve himself or commit suicide over the phone. As long as there are at least 3 papers left on the wall, he'll live. That’s why I suggest saving before you entered this apartment. Don’t save again until after you get back to the Daily News Times station.
Go back to the Daily News Times to use a computer. You’ll end up talking to Jack. Here is where your earlier choices affect this conversation. He’s supposed to offer you a ride out of Dubstown. If he doesn’t, then perhaps you should re-think your answers to the questions he asked. If you’re too lazy to do that and you’ve got enough money to buy a bus ticket out of Dubstown, then I suppose that works too, but hey, it’s a FREE RIDE with Jack. By the way, a bus ticket would cost $800, so I doubt you’d wanna spend that much money.