Does it matter who messages first?

I've been messaging the guy I like and I'm trying to figure out if he likes me back. Do I come off as too desperate if I'm the one who usually messages first? This may be a little obsessive, but I counted it up, and I've initiated the conversation 8 times while he's only initiated 4. Would it be bad for me to message him tonight (the last message was Thursday)? If not, what are some things I could say to him? Thanks in advance!
Does it matter who messages first?
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