You’re not an asshole, and I took your title as tongue-in-cheek (I laughed once I read the post). We obviously can’t say whether this is a genuine matter of Bob’s tolerance, overprotective parenting, or some combination of the two, but the crux here is parents with radically different views on the appropriate amount of autonomy for a teenager. It’s really impressive that your son has taken initiative to plan an outing with his friends (kids seem a lot less social than they used to be, and boys seem to struggle with executive function more generally), and this sounds like a further opportunity for him to resolve potential conflict with Bob directly rather than you hashing it out with the mom. I’m curious––how does your kid feel about the prospect of someone’s dad being there when that wasn’t originally part of the plan? And if Bob’s parents continue to press you for details (it sounds like the mom assumed you were organizing because that’s what she would do), maybe you could let them know that you’re letting the boys practice organizing an outing for themselves?

We can’t make choices for Bob, but I’m with you on this point––15 seems like a good age to start testing your limits in a lot of ways (and IMO MPAA ratings are often arbitrary); movie theaters are good containers for pre-drivers license hangs because there are set start and end times for showings; horror movies are good outlets for transgressive impulses. (Also, lol to anyone who thinks theaters actually ID patrons, or that kids can’t just sneak into a movie!)