In most ways, Ollie wasn't like most people. In most ways he looked at the world with a different view, something he and his sister always called "thief goggles" that made them see things far differently from everyone else. There were very few people he saw as people; most of them he saw as potential targets (the obvious exceptions being Allie and his uncle, wherever he may have been), people with stuff he wanted that he should have. That number grew by the day. It should've concerned him. On some level, it already did. But it was easier to ignore that concern of late.
Did that mean he was losing his humanity to this thing? Suddenly he was concerned about that.
One way that he was like most people, though, was his hatred of nighttime travel in this new world. As a matter of fact? He'd have probably turned "Lady Ricardo" down if (s)he had asked for somewhere much further away from Grand Central than that apartment complex. But as it stood, it wasn't a problem. Yeah, he was still a little bit worried about it, because it was being out and about at night and he was much less a fan of that than he had been when he'd done his heists. But he'd be okay. It wasn't too far from Federal Hall, after all.
Convincing Allie of the necessity of this had been another matter entirely. He loved his sister dearly, truly he did. But she worried too much. Ollie was a survivor, after all. He'd considered sneaking out after she fell asleep, but for two reasons, he decided it wasn't such a good idea. One, he felt guilty being dishonest with Allie and two, really didn't want to leave after dark. So, after much protestation, he gathered the bottle of Cognac he'd gathered from the safehouse kitchen and headed to the exit. He'd have to loot her something while he was there. Something pretty. Those were her favorite things, after all.
Regardless of that fear, he headed out to this abandoned apartment building to meet up with whoever this Lady Ricardo was. Boy would he be pissed if it was some random dude in drag or something. Lady? Ricardo? It would make perfect sense. And it would be just his luck. He thinks he's going to meet with some chick to have a drink and he ends up meeting with a drag queen. Though a drag queen in the apocalypse would be pretty epic.
The walk (or jog, as it were) was relatively uneventful, thankfully. He'd gone by rooftop and he'd seen a couple of groups of infected down on the ground but he hadn't paid them too much mind because he was safe up here. When he got to the designated meeting building, he opened the door to the rooftop and hurried down to the apartment they'd decided to meet at, knocking on the door and waiting somewhat anxiously for this "Lady" to let him in.