#4 Ask for his help with something. As I mentioned above, shy guys are generally REALLY nice people, and you should appeal to this quality in him by asking for his help. He won’t be as shy if he thinks he’s just helping you, but it gives you the chance to flirt while he’s doing so.
#5 Ask a lot of questions – not directly about him. Asking questions is the best way to get someone to talk. Preferably, ask questions that require more than a yes or a no answer. This forces him to talk to you, and the more he talks to you, the most he’ll open up, and then you can start flirting confidently.
#6 Don’t be aggressive. Aggression with flirting has its benefits, but only if the guy isn’t shy. If he is, this will more than likely just scare him away, and he’ll be too nervous to talk to you again. Be timid when you start flirting, and then your chances of him opening up are much better.
#7 Avoid the teasing technique. Teasing is a really great tool to use when flirting as long as the guy isn’t really shy. If you want to know how to flirt with a shy guy, teasing will only make him more self-conscious and even more shy, so avoid it until you get to know him better.
#8 Flirt infrequently. Don’t just go up to him and flirt every single day. He’ll be overwhelmed and will probably start to avoid you since he doesn’t like when he’s super nervous. Start every few days, and then increase it until he’s actively responding to your flirting.