I admit that at times it is uncomfortable for me, perhaps because I'm still a bit too classic when in comes to social manners.
First of all, I'm used to expect a sign. I don't know if this makes sense to you.. like for instance, when kissing a hand I don't go and grab the hand. I'll wait for the woman to move her hand slightly and then extend mine before she fully extends her forearm to hold her hand. Unfortunately this is rare today and it is only possible with women of the age of my mother.
Middle aged women might do it, but then when you hold her hand you notice something strange. Her hand is in a vertical position, not horizontal. In other words, they expect an "almost" as shake-hand.
Don't get me wrong. When I say kiss the hand I don't literally mean it, like in taking her hand and your head close and actually kiss, while bowing.
As for cheek kissing, which is done once on each cheek here, what I usually do is to put my cheek next to hers while holding her hand. Unless she is a good friend or a relative. And always after I notice that she expects me to do it.
One funny thing that happened time ago. I was going out with a girl and we had dated in some place. I told her that I would come along with a Spanish friend. She then told me that she would come with a friend of hers.
My friend told me that he would arrive a few minutes later, on his own. When I arrived, she introduced me to her friend. Obviously, her friend knew that for Spaniards it was usual to kiss both cheeks, so she approached her face when I held her hand. The bad news were that her face looked as if it had never recovered from a bad chickenpox. I did my best to put my cheeks next to hers.
When my friend arrived he first cheered my girlfriend with the usual cheek kissing. Then we introduced him to her friend and she did the same as with me.. my friend froze! His eyes opened wide and he couldn't help pulling a face between surprise and disgust.. he then pulled back a little and stretched his arm to her. It was a violent scene...
Later, I tried to apologize to my girlfriend for my friend's behaviour, trying to make her understand. She laughed out and told me that she actually understood my friend, but she couldn't understand how I dared to kiss her on the face!
