Take it steady, and learn to read the body language.
When you are walking, slip your hand into his. If he grasps it, fine, if not, slip it away again - no harm done, no dignity lost.
A great way to guage if a kiss is appropriate is to try this -
when you part for the evening, stand close and look into his eyes. Move your mouth towards his, and see if he responds. if he does, place your lips against his, and press very gently - if he responds, great, if not, he may be shy, but you have let him know it;s what you would like.
If when you move towards him, he either turns away or backs off, simply move away from his mouth and kiss him gently on the cheek. Again, dignity intact, no awkwardness, no difficult 'conversations'.
My guess is he will respond, and be grateful that you have taken the lead. A lot of guys simply don't know how to read signals, so they need a bit of guidance.
Let us know how you get on.