Hi Samantha,
It may be easier for the both of you to talk to each other over an extended period of time if you were both not at work.
Oftentimes, workers hang out after work to unwind. Find out if he has a crew that he hangs out with from time to time after work.
If he does, find out the next time that they are all going to be hanging out after work and get your own crew of work friends to accompany you to wherever it is that they will be meeting up.
Meeting each other outside of work may help to move things along. It puts the both of you in an environment where you can both relax and ultimately talk in a much more elaborate and free manner.