Most Helpful Guy
I think when both sides are shy, it is best to start with something low-key (the round of coffee or taking in the local football game or w/e). Your generation texts more than calls, so just text it if you like, and I think texting is appropriate for low-key activities with low priority.
Start with that mindset and just be yourself. You'll learn enough about him even from light events that you'll know whether or not you want to continue with it.