1. Work on how you organize your story telling. That was difficult to read.
2. The fact that he asked you why you never text him first, and actually stated that you don't annoy him, means that he's being honest when he says that you don't annoy him.
3. Us guys like for a girl to occasionally text us first because it shows that they're interested. We worry constantly if a girl really wants to talk to us, or if they're just being nice and putting up with our annoying texts. Make him text you first most of the time, but occasionally, you should initiate the conversation.
How big is the age difference if you don't mind me asking?
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well he might want to see how much you like him and even if there an age difference doesn't mean he won't like you.
maybe he needs to feel like you really do like him, and I agree with rthomas43
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