In the virtual world, everything happens very quickly: The best questions are entertaining to ponder, and specific enough that coming up with a response is easy. For an icebreaker question to be effective on a dating site or app, it needs to accomplish 3 things: If you want to get to know someone, ask about their proudest achievements. What did you do last weekend?
If your guy is competitive, he may be more willing to participate if you make it a game with rules and points.
Online Dating Questions to Ask Before Meeting