Well, a New Year's bash is a definite yes for Kieran, naturally. And he'll appreciate TJ keeping him on track when he gets his grades, although he might make faces and complain during the actual studying. And he will listen to TJ's arguments for musical theatre, but probably won't admit if he wins and he starts secretly liking musicals. At least not that easily.
I can imagine. Although Kieran can manage some basic sports stuff, he usually actually just flails around when he tries, so he doesn't really try at all. And he'll enjoy Jackson's constant music stuff, really. Although he's actually pretty ace at memorization, generally stemming from running lines in his head all the time, so history is good with him because all you have to do is memorize. This is also why he sucks at math and languages, incidentally.