#13 Make him laugh. Laughter has the ability to open even the most closed-off people. So, tell him jokes or just start joking around, even in a group that he’s in. If he can feel like he can laugh with you, he’ll be more comfortable around you and it’ll be easier to flirt with him.
#14 Be consistent. Shy guys have insecurity issues *usually*, so it’s a good idea to make sure he knows you’re flirting and not just being friendly. His default is going to be to think you’re not interested in him, so be consistent with your flirting so he knows you actually like him.
#15 Make eye contact. When you talk to him, he may want to look away from you because that’s what shy people do, but do your best to catch his eye. Making eye contact creates a kind of intimacy that’ll make him feel like he can trust you, and then you can get in any kind of flirting you want!
If you want to know how to flirt with a shy guy, you need to allow him to open up to you and trust you naturally. If you force your flirtations upon him, he’ll be more likely to run away than flirt back.