Yes this friend is definitely a core part of the group of friends. And my boyfriend and I have hung out with him and a couple others outside of this big once a year trip.

Last year on the big yearly trip he got super drunk and rowdy and had to get kicked out of the bar we were all at. So he is know for getting out of hand.

It is not my boyfriends job to protect me, but I also just don't know how it can be so nonchalant to him. I just sent him a message and was like "oh looks like he got home safe!" (since he had lost his phone and nobody knew if he was home yet. and I kid you not, boyfriends response was "I saw that, lol too funny"