@anotherglass being "concerned" for our children, irrespective of their age, is not unusual.
Your son, seems to feel that your concern is intrusive, undermines his (perceived) ability to safely navigate his life and to him, shows you don't trust him. (which you obviously don't, given his past behaviours)
So how can you improve your relationship with him @anotherglass?
Comparing his attitude to your other lad is totally fruitless, they are not identikit children, so may be don't do that.
How best to alleviate your worry for him requires you to re-adjust your expectations, I think.
Asking where he is going and with whom, is a non-starter, for him.
How exactly, do you think, you could keep him safe now that he's an adult?
You can't, that's totally within his remit now, isn't it?
So what do you really need to know from him that is not intrusive (to him) but reduces your anxiety?
Letting them fly is fraught, I really do understand @anotherglass