How long does it take a shy guy to open up?

jesshicuh09
We've been friends for almost two years now. We've fooled around twice recently, but both times he had get some drinks in him before he made a move.

He seems really into me when we're together, and he's really flirty over texts, but we can go several days without talking until I message him again. He always seems happy to hear from me, but it makes me insecure that I have to do a lot of the initiating.
How long does it take a shy guy to open up?
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