So you want to try create the right moments for deeper conversation, I think that would be more likely away from his mates? I don’t know them so just guessing.
With that in mind, maybe Google around for anything interesting or different happening in the area. A gardening or book faire, wine or coffee festival, anything relaxed. Then ask him if he wants to go. Ideally something quiet that has some walking around?
That might create helpful conditions.
Any one want to guess who will really end up paying for the price hike?
It’s not AT&T.