He may have the courage sometime, but it will probably take a while. If you get the opportunity, you should kiss him first. Since he actually likes you and he is shy, he will most likely love it. At least I did when my girlfriend kissed me (we were almost in the same situation, the difference is that we weren't REALLY dating yet)
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It sounds like he likes you. You could challenge him to some sort of contest, that if you lose you will give him a kiss. Then make sure you lose.
Or you could what until he sits down, and then sit in his lap. From there it shouldn't be hard to reach his lips.
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Ask him "wanna kiss me?"... if he says "no" ... tell him "i didn't say you could"... if he says "yes"... then say "ok lets try it"... WHO KNOWS... he probably has never kissed anybody other than his mother... you need to encourage him... and he needs to understand that it takes practice to kiss good... not many are naturals.
That's why some guys made women feel anxious because they're not taking initiatives to go for what they want, in this case making women feel insecure. You may making small touches on him and he may start reciprocrating if he knows.
Shyness isn't the issue, he is just insecure about it. An honest conversation can go a long way. Just talk to him about it.
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