The few times I talked to guys in this way, we weren't necessarily "flirtatious" in conversation, but we at least knew we had interest in each other. The guy I'm talking to currently isn't the usual "calm/quiet" guys I usually talk to. His outgoingness makes me feel like he's gone around, hence why he expects me to be a certain way when I talk to him.
But I guess it doesn't hurt to try... so tell me!!