The question is what do you want to know about him? You can be playful and sext with him, but is that giving you the information you want to know? If not, what's preventing you from showing interest in those areas?
If you feel stuck, you're not where you want to be. Identify where you want to be and then seek a path to get there. Going with the flow will just take you in circles.
Long distance relationships are very challenging, as people either see what they want to see or what they fear seeing, but it can be near impossible to have an accurate picture. You'll always be limited by what the other is willing to share. The more distanced the relationship, the easier it is to show the other only what you want that person to see. It's very hard to keep people from seeing who we are if we're living together.
Start asking him questions about his life -- what he enjoys, etc.
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Play truth or dare while sexting or just before
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