Robert shrugged at her rather harsh words of not being able to get stood up if it was non existent. But he agreed with her nonetheless. He ordered a glass of his favorite scotch. When she said she was expecting to run in to someone, he turned his attention to her. "I know I've been gone for a while, but the Marian Anderson I remember was smart, loyal, caring, beautiful... If you're half of anything you used to be, this guy you're waiting for is really going to miss out." Robert said casually, nodding a thanks to the bartender as he came back for his drink. "What's this guy like? Obviously nothing like Eddy. And I'm guessing not a cocky lawyer who fell on his ass. He's gotta be someone great to get your attention."

He was somewhat enjoying this. Guilting her a bit from all the things he's heard about him from others, knowing exactly who she was waiting for, and he really wanted to know what she thought of him-- well, Robin Hood... But he was the same guy! And hopefully he wasn't being too much like his old self. He hadn't told her how "hot she looked." he didn't tell her she should be more focused on him, and he tried so very hard not to look her up and down, even though his mind was pleading to look at her in all her glory. If he really needed to he could spark her interest in saying he knew a thing or two about this masked man, but at the same time he didn't want to play it that way. 

He already was head over heels for her, and he wanted her to fall for him. He didn't really want to trick her in to liking him. And no, this wasn't a form of tricking. This was simply using his resources to get her to talk to Robin to show her that he's not the asshole he used to be. Worst case scenario: She falls for Robin, and Robin can show her his real identity-- But that's the last resort. He didn't like the idea of revealing himself as Robin Hood and then getting laughed at, or vomiting for thinking she was attracted to him, or anything like that...