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Try and get him to tell you something you don’t know. It’s a win win.

Question 14: Which celebrity would make the worst leader of a country?

What really makes this question fun is imagining what the celebrity would do once they were leader and what kinds of laws they would make.

To keep the conversation going, keep switching out the celebrity.

Question 15: What were you really into when you were younger but now think is silly?

Find out what embarrassing things he was into when he was a kid.

Great ammo for some good natured teasing later annette duffy dating on.

What kind of hidden talents does he have?

This is always great because usually he can show you. We all have silly and useless talents, now you can learn about his!

A seemingly simple question that sometimes can lead to a really long discussion. That’s because usually behind every broken or lost phone there is a story. Either that or he is just super clumsy or forgetful, which is also good to know.

Question 18: Which historical figure wasnt as amazing as most people think they were?

I know not everyone is into history. But even if he has only a passing interest in history, he’ll probably like this question. After all, like they say, “Great men are seldom good men”.

Plus you might learn something you didn’t know about a famous historical figure. Or you could skip this one if you both couldn’t care less about history. If you do decide to go for this one, be sure to do a bit of research and find one if you don’t already have one in mind.

Question 19: You are in charge of making insects a popular food item. You have 1 billion annapolis dating US dollars to achieve your goal. How do you do it?

Here is another creative one. You can see how quickly he can think on his feet and how creative he is at solving problems. Sure it’s a bit of a random question, but it’s a fun way to talk through some creative ideas. Plus, solving a problem together is a great way to have a conversation that doesn’t feel forced.

Question 20: What is the highest pressure situation you have experienced and how did you handle it?

Similar to the drop the mic moment question, this one will give him a chance to tell you about a story that is important to him. Just know that there will probably be some exaggeration and embellishment happening when he tells you the story, even if he doesn’t mean to.

Memory is a severely flawed thing after all!

Question 21: What’s something you were really stressed about, it turned out to be no big deal?

A fun question to answer, but also very informative. You can find out what types of things stress him out and you can also see how high strung or laid back he is. Plus it’s another chance for a story, and almost everyone likes telling stories about themselves.

With a 24 hour news cycle there’s always some news story or phenomenon that’s past its interest expiration date.

Ask him this question and you can see what types of things he doesn’t have patience for and it will also let you know what topics to avoid in conversation.

Question 23: What three events made the biggest impact on who you are today?

One of the best questions you can ask a guy.

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