Be like: dude, your sucking the life out life out of me here! Then ask him what songs he likes and out of no where yell out: WOW FANTASTIC BABY! And See his reaction and say something like: hey wanna see which one of us can talk about the most interesting stuff? Or: hey wanna see which one of us can get more hyper active while texting?
I so know how you feel! xD this kid is always sending the most boring and shortest responses im always doing the talking but he messages me first so its like if your gonna be boring why do you message me ._. anyways you should just ask questions that will lead to more stuff so you don't run our of ideas.
its not just the problem with guys.......i dated few girls and its also difficult for guys to answer things fluently in the chat....what i figured out was, girls wants guys to push conversation...girls dont talk much or reply late...that is so annoying..girls wanna test us. why can't girls take initiative and ask us few things. that is not going to make you look inferior. What you need to do is figure out if you really like this guy or not. if not leave it...if you do then make your efforts to know him...ask him about his life and stuff...music sports movies..lots of topics to discuss...girls are way more mature as compared to guys they know a lot whats going on in guys mind