How do I talk to my crush or initiate a conversation (I'm shy around him)?

Anonymous
I really like this guy and I want to talk to him because he's such a great person and because I want to get to know him better. But every time I get a chance I wimp out or I think he might initiate first so I wait and a lot of the time he doesn't and then I've missed my chance. I can always think of things I could've said afterwards or imagined what I could say, but whenever I actually get the opportunity I either don't realize it or get shy. A part of me also just wants to see if he will initiate first bc it usually is him rather than me. I know i should just go up to him and say something, but thats when the part of me that wants to wait for the right moment steps in... and there never seems to be a right moment... although im sure it's just me. Also i never know what to say in the moment while talkig to him... I always feel stupid afterwards and can think of perfect things to say only AFTER its happened. But he hasn't talked to me for while and I really just want to get to know him and become good friends... how do I break the ice? How do I say what I actually want to say while talking to him? Advice?
Updates:
+1 y
I realized that I'm not actually nervous around him... I just can't talk normally or with ease around him for some reason... or approach him... so how can I talk to him or approach him with out backing away at the last second all of the time?
+1 y
What are some cute things to say to initiate a conversation with him or while talking to him?
How do I talk to my crush or initiate a conversation (I'm shy around him)?
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