He'd known O'Connors was alive, of course. That was the benefit of checking one's own journal. In fact, he'd discovered quite a few people he'd thought might have gotten themselves killed had actually made out quite well - or at least as well as "living" and "in possession of all your limbs" qualified. But he hadn't been to liberal with contacting them, at least under his own signature. In fact, he probably shouldn't have contacted O'Connors. Or Diana, really.
Still, he was surprised to see her working here. At first, he wasn't really sure it was O'Connors, despite the fact that the waitress looked and sounded like her (especially since she sounded annoyed that he just happened to come in and ask a question). But he decided for a moment that his mind was just playing tricks on him - that he hadn't gotten properly high in a while and that his brain was just making up the difference.
So immediately he was proved wrong the second he started walking over to any old random table. He turned around, eyes a bit wide. He let her lead him over to a table before deciding he shouldn't have been so shocked. From the first few seconds of their encounter, he decided that she hadn't changed much, aside from the fact that she was a waitress. But he counted his blessings.
Sitting down, he smirked and said, "Well how do you think I feel?" Then he grew quiet, making sure the Muggles couldn't hear. "I'm meeting someone I do work for. He says this is the only safe place now. What are you doing here, O'Connors?"