Look, it's not that he doesn't trust you. Of course he trusts you. But Dick knows you've been sneaking out recently, and he has concerns.

Gotham's a dangerous city. You all know that. And sure, he's not really got any place to lecture about being out on the streets at night, considering 'spending time on the streets at night' is kind of the family business. But there's a difference, absolutely is, between going out on patrol costumed up and with backup on call and all safely patched in to Oracle's system; and sneaking out of the Manor to creep off and do who knows what at odd hours.

You could be getting up to trouble. You could be in trouble. You will be in trouble, if Bruce catches on. Dick can only be sure he hasn't already clocked you by the fact that there hasn't been a blow-up about it, but it's Bruce. It's only a matter of time. He's actually kind of impressed you've managed to keep it under the radar this long.

And look. He gets it. He had his own little rebel phase. They all did. Jason's still having one (he kids... mostly). But it was just as dangerous when he was doing it, and just as not smart. And it's his job as the elder brother of the Family to try to keep you all from making some of the same mistakes he did, right?

And what if there's something more serious going on? What if you've fallen into some sort of... dangerous activity, or risky crowd? What if something's making you want to leave the Manor, something you feel like you can't tell the Family? What if something's wrong? He can't just turn a blind eye.

All of this to say, the fact that he's waiting on the Manor grounds outside your window right now, ready to step out of the shadows to confront you as soon as you finish your climb down (hey they've all climbed out a few windows in their day, right? Scaling the Manor walls is a cakewalk anymore) isn't because he doesn't trust you. It's because he's worried about you.