It was hard for Ollie to stifle his laugh when "Lady" mentioned not trusting the Man. Really? All he could think of was that movie he'd watched when he was a kid… School of Rock or whatever, where Jack Black had been super obsessed with not conforming. He supposed that maybe it was reasonable to be wary of the Man in a society where the aforementioned Man seemed to be in charge of everything, right down to who lived and died. "Lady is suspicious of the Man. That sounds like the plot to a bad romantic drama movie, doesn't it? Something that Julia Roberts would star in undoubtedly."
He chuckled and arched an eyebrow. "I was figuring that it wasn't. Just a hunch," he smirked again. "Well, you have my real name. At least most of it. But if you're not comfortable giving yours, I'm okay with that. We're relative strangers, after all," he mused, watching as she made her way toward the window and the fire escape. He brushed a hand through his hair, thinking that it was a little peculiar that she was okay to drink his booze but not give him her name, but what did it really matter?
Ollie wandered up to the window once "Lady" made her way outside. He gathered one of his pistols from his backpack, just in case, and followed her lead, albeit a little more swiftly. He was a little less worried, which probably had more to do with the fact that he was the thief around here, and anything that was in that bag could easily be replaced next time he went on a supply run. So, he handed her the light, leaving him in relative darkness for a little while, then dropped his bag out through the window, before using the top of the window to lift himself and put his legs outside first. He slid out the window and took a seat on the floor.
"So, Ladyface," he half-smiled, since he too had noted that he didn't know her name, even though he didn't particularly mind. "How do you feel about Cognac?" he asked, picking the bag back up and digging through it to get the bottle and the two glasses that he'd managed to swipe from the Federal Hall kitchen.