She thought he was charming? He tried to ignore the "stupid jokes" part, because the other parts were things he didn't really hear from everyone. It seems the only thing people see him as is a thief or savior. He was a gentleman out to try to make people's lives better by helping them with the lousy economy that this city has. He raised his eyebrows at the comment of him caring was weird, but then lowered them when she explained it wasn't a bad weird. He took a sip of his drink, and almost coughed when she said she wasn't anything special. It wasn't supposed to be dramatic, or to make his point. He was in love with this woman, and admired a lot about what she has done. He looked over at her, and gave a smile. "Every single guy, single or not, keeps glancing over at you." He said. He was a lawyer for quite some time, and now a professional pickpocket. he was very observant, and easily noticed that. 

"You have everyone's attention, and they don't even know you. If this mystery man knows even the smallest bit about you, he's most likely going crazy thinking about you. Thinking if you approve of every one of his actions, even the smallest ones, if he is the man that deserves someone like you..." He paused, and looked over at her, then shook his head. "I've been gone for a while. Read a lot of books, especially romance novels..." He explained weakly, trying to hide that he was speaking a bit too much from the heart. He waved the bartender over and ordered another drink.

"The point is, if you got dressed up to become the most beautiful woman in New York for this guy, he'll do his damnest to be here to not let you down, or its his loss."