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When should I make a move?

I get told all the time by girls that I'm too shy. I'm outgoing, but I'm shy in a way that makes me afraid to make a move on my girlfriend and this has affected my previous relationships. I'm mostly afraid of rejection by the girl I'm trying to make a move on.

Sometimes it's a move like cuddling with her, but other times kissing her. Either way I'm afraid to because I don't want to get rejected. I don't know when the best time to make a move is or anything about making the right moves and this prevents me from getting girlfriends and sometimes even break ups.

My previous girlfriend told me it was okay to make a move while we were discussing my shyness and I still never did. I'd hold her hand and cuddle with her but it would take a long time of self persuasion to do so. I need help to know what girls prefer making a good move is and whens the best time to do so. Guys are welcome to help me out as well but I'm liking this girl a lot and I don't know when to make a move or even how to and I don't want to lose my chances with her
When should I make a move?
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