Who Is Your Closest Female Friend?
One of your first questions should be to ask a man whom he considers his closest female friend.
It can give you valuable insight into how he views women, his sensitivity and the qualities he values in a woman, even at a platonic level. You may also be to gauge if he has any latent romantic feelings for that person. If that person is a relative such as his sister or mother, you can draw some other conclusions about his family dynamics and whether he may be too attached to his mother for your liking.
What Things Are You Most Proud of in Your Life?
Asking a man what he's most proud of in his life can reveal what he considers important and give you an idea how you might fit into his life.
If a man lists athletic accomplishments, educational degrees or a job promotion, you may reason that he values his physical attributes and is results-driven. If he answers in a way that's less defined, such as talking about staying true to himself and always striving to be honest, it could be a sign that he's more interested in self-development than a specific set of goals. Of course, no one answer will fully define a man, but this question can at least give you an idea about how he thinks about himself.
Name an Extreme Sport You'd Like to Try
You may not be all that sports-oriented yourself, but asking a man to name an extreme sport he'd like to try will provide clues about his willingness to take risks and be adventurous.
If he doesn't have an answer or the idea of extreme sports bores him, it could be that he just doesn't respond to that activity, or it could signal that he's not the kind of man who'll act spontaneously in a relationship.
What Animal Would You Be if You Weren't Human?
Asking a man what animal he would be if he wasn't human may seem odd and out of left field, but it may be an effective way to see how he thinks about nature, the world around him and himself.
It's likely that he's never had to answer this question before, which will force him to come up with an answer that's spontaneous and unexpected, giving you a small glimpse into his personality. If he imagines himself as a lion or tiger or some other predator, it could mean he views himself as strong and powerful, always going after what he wants. If he responds by saying a bird or another animal that can fly, it could indicate a desire for freedom and adventure. Again, his answer won't reveal everything, so you shouldn't draw any broad conclusions, but let your instincts guide you based on the answer you hear.