If he usually is the first to text you then I think it'll be okay to text him first. You should text him first every once a while. It shows that you're interested in him just as equally as he is into you. And I think texting him "hey you :) how was your day?" will be just fine. (:
Girl just do it. Be confident and if he reacts weird then that's his problem because that is completely fine to text.
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I think you should text him "hey you how your day?" It shows that you care about him.
And guys like a girls that text first when they are shy to do it.
I don't see why not.
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