She laughed when he agreed that he had in fact danced, "It looked like you were having fun," She told him, just to try and smooth over his annoyance as he pulled himself up to sit on the counter top. "I hate to break it to you, but there wasn't anyone at the party who didn't see you, I don't think it counts as spying at that point." Besides it had been nice to see him acting goofy for a change, something a little bit more like his own age and not the overly dour and vaguely threatening person she'd known him to be up to that point.
But for now - there was apparently something more serious on his mind and Barbara could let up if she thought there was something important on the line.
She leaned back against another counter a little as he spoke, listening to him work out his hypothetical question realizing that of course he meant himself though who exactly he wanted to approach was another matter all together but it was pretty obvious both from the phrasing as well as the way he'd slowly worked his way through asking the question that he didn't really want to get into details.
"Hypothetically," She began rather pointedly, "I think the best way to do something like that might be to just start spending more time with that person. So you can get to know them better, and they can get to know you better too." She didn't want to shove him into the deep end after all, starting slow and easy felt like the best advice she could give. "Sharing a meal together is often a good indicator that you're interested in something a little more than friendship." She added.