Remember that non-verbal cues are incredibly important to watch. It's not just what you say, but how you say it - with your voice and your body. When people sense a dating prospect, their awareness of the "little things" becomes heightened, even if only on a sub-conscious level. Many just chalk it up to "vibe". Be yourself, and relax. You need to let him know that you're comfortable talking to him. Make eye contact when you speak, and always maintain that eye contact when he speaks. Keep the conversation light, and have fun. Remember to let yourself laugh naturally (as opposed to forcing laughter). General signs of awkwardness are obvious when you think about them. Eyes that dart suddenly away, wincing, eyes that don't smile when he does, or gestures such as rubbing his neck or closing his posture by crossing his arms can mean he's uncomfortable or just not digging you right now. Things such as fidgeting or rapidly tapping objects (if your seated at a table) can mean this too. Also, if he's insecure, both hands will be crammed down his pockets; if seated, he may rock front to back a little bit. If you see stuff like this, back off just a little, and remember that it doesn't necessarily mean he's repulsed by you - he could just be having an off day, has something on his mind, or maybe is a little insecure about himself (maybe he wishes he'd worn a better outfit or had a chance to remove spinach from his teeth; yes, we can be every bit as self-conscious as women in the presence of a flirt). Pay him a compliment, and lighten the conversation a bit. If you back off a little and you still sense he's not feeling it, gracefully end the conversation and try again later. If he has smiling eyes, opens his posture (talking with his hands or sitting with his legs apart), mirrors your body language, or tilts his head and brushes his face while listening to you, then you're getting the green light. Closing distance is important. You don't need to get in his face, but gradually bring yourself closer as the conversation goes on. If he seems comfortable, find ways to break the touch barrier without being too forward (like brushing against him, or touching his back or arm). Above all, be yourself and relax. Have fun - it's what getting to know someone is about.