That happened to me recently. I was chatting with this girl from school, writing like 5 lines, she'd reply with 'hahahah' and stuff, and I would think all was going well. I would start asking questions too just to revive the chat once in a while, but at some point it becomes awkward and I realize that I've become too annoying and intrusive.
What I would suggest is to keep your texts very short and to the point (long ones are scary) and not to keep every answer open-ended, otherwise the person will be trapped in the conversation. The more you leave someone free to answer or not, the more their behaviour will show if they really want to talk to you or not.
Also, it's pretty hard to maintain a long conversation without talking too much about yourself (even if it's not narcissism you still steal the attention) or asking too much about him (which can be a bit creepy if not moderated).
More importantly, don't think too much about it and don't try to interpret signs because scenarios in your head are not likely to be what's really happening.
I hope all will go well!