It is really important that you ask the right questions at the right time, since inappropriately timed questions can hamper your chances of winning another date.
Listed below are some questions that get you going, but it is up to you to figure out the right time to ask them.
Try some general ones like these or choose a theme and let the conversation roll from there.
From pop culture and phone apps to old favorites and magazine subscriptions, learning about a person's media preferences can give you insight into who they are early in a relationship.
It's also fun to ask questions that compare where someone thought they would be at this age to where they actually are now.
You could set this up as a game and ask each other as many "favorites" type questions as possible within an allotted amount of time.
These questions need to be asked at the right time judging the mood of the moment.
Try to keep the questions to a reasonable amount, say maybe 5 to 6 questions per date. - Does your first love still hold a special place in your heart? - If your partner wants to do something you don't particularly like/enjoy, would you do it with him? - Do you like going to the theater or for concerts? - Which is the one place you would like to visit/settle in?
If you're relaxed together, feel free to ask these questions and share a few good laughs.
You should be willing to answer questions too, just to keep things fair.
Obviously, certain questions are appropriate for different phases of a relationship.
You wouldn't want to ask someone on the second date to reveal to you what most people don't know about him, but you may be able to if you've been together for several months.