His confusion at the younger generation seems mostly due to his trying to piece together the reality from lingo, pop culture and conversations overheard.

E.g. sexting is no more a substitute for physical interaction than the phone was/is. it's still all about contextualizing and coordinating actual physical interaction.

"go places in a group of friends" is more a precursor to a traditional date. It's the meet-and-greet stage, without being explicitly paired off to lower the pressure and expectation. It's also (in large part) a side effect of suburbanization. When you need a ride from a parent to get anywhere, it's a lot simpler and more discrete to say "group of friends" than "this girl I want to get to know". The goal of most kids in any such group is still to ditch the friends.

At least, in my day it was. Which wasn't all that long ago, but technology makes social behavior a fast-moving target.