How to get someone to open up over text?

[Anonymous]

So I'm texting this guy I knew from school. We talked a little but not a lot as he had to switch schools soon after. Well when he first left I fb him and he ended up giving me his #. We haven't talked in a long time but last night I texted. we talked a bit but now I'm stuck.I want to keep the convo going but I'm running out of ideas. He's a shy very insecure person, kinda closed off in general (I'm guessing because of stuff that's happened in his life) and can be hard to talk to sometimes. But I wanna get to know him and get him to open up but I don't know know how. I want to talk to him about our common interest-cooking but I'm afraid talking about that might make him upset because he's currently un able to pursue that like I am because he had to switch school. But I don't know what else to say.. I don't wanna ask a bunch of random questions and annoy him but I feel like most other things would be convo killers or annoy or weird him out... Ideas? Do you think I shouldn't talk about cooking?

[CookieRaider959]

I smiled a little when you write " Do you think I shouldn't talk about cooking?" If he is a shy guy than anything you write will be interesting to him. The best things to write about is yourself. Write about how you feel, or what you did. That will keep the conversation going. When he hears all these things about you he will start talking about himself. Don't worry about annoying him. He probably will be like "yesss a cute girl is texting me" whenever you text him.