Keeping a (non-sexual) conversation going is a lot easier if you've

• - met through a common hobby/life situation/etc. on the internet.
• - met enough times in real life to realize that you have actually have things in common.

As the situation stands, you're probably better off asking a variety of questions that can't be answered with a simple yes/no. You can start with something general (how was your day) and the go into detail (so why did you buy those kind of shoes). If you're forgetful you might want to take notes, so you can remember to ask about things they mentioned in the past.

Just don't take it too seriously. The longer you text, the more likely it is you'll get your heart broken when you eventually meet and realize there's nothing there.