Should I text him first this time?

So he has initiated like all the time but I have only initiated text one time. There have been times when we did not text for like 2 weeks (idk if he was testing me lol..) and he suddenly messages me out of the blue and asks how I am doing. Yesterday we had a really interesting convo and texted for hours. But then our convo ended with me texting "It's okay :)". And he didn't reply back -_-

So do I text him first today? Or wait for him to text me like last time... and no he's not my boyfriend, just an online friend. I feel like I bother him by texting first but at the same time he says he finds me beautiful. So wtf am I supposed to do o. o Message him first?
Should I text him first this time?
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