If you have been dating a guy you know to be very shy for 5 months and still havent kissed how do you tell if hes shy or uninterested in being physical and how do you encourage him subtly?

Talk to him privately and ask what he thinks. If he's not ready to kiss, don't push him. Give him about a month, and then start flirting-but only barely. Don't try holding his hands or anything. Just start talking to him in a flirty way, and if he's interested, then he'll flirt back. if hes not interested, he'll look kinda bored, and that's when you need to change the subject. if he just sits there with a blank look on his face, hes most likely day-dreaming, and you need to snap him out of it. if he isn't interested, then either youll have to live without kissing him for a while, or it's time to move on.