Basic Questions
The basic questions are like the logistical framework of your boyfriend. They start with things like "What is your favorite..." and then go on to list something innocent and innocuous. Start with the simple things - ice cream, color, holiday, car - and then get into more unusual questions. Instead of, "What's your favorite TV show?" try "What's the funniest thing your favorite TV character ever did?" Keep these factual; you can use them later on when it's time to buy a gift, or make him happy when he's feeling down by showing up with a poster from his favorite movie.
Romantic Questions
You may be tempted to ask basic romantic questions like "Do you love me more than you did your last lover?" but keep in mind that men have been conditioned to regard that - and many other questions involving romance - as traps designed to make them say something they will regret. You need to make sure, if you are asking questions about feelings, to make them feel safe and not put on the spot. Questions about concrete moments will be easier than abstract emotions: What reminds you of me when I'm not around? or If you could take me on a romantic vacation anywhere in the world, where would we go? works better than, How do you feel when you look in my eyes? You should throw in a few abstract questions at the end, just to see if a warm up could get him to open up. However, make sure you don't get upset at his answers, because if you get angry, it will be the last time he answers questions like that.
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