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50 Engaging Questions to Ask a Guy for Deeper, Meaningful Conversations

Thought-Provoking and Fun Questions

  1. If you could have dinner with any historical figure, who would it be?
  2. What’s one fictional character you relate to?
  3. Do you believe in fate, or do we control our destiny?
  4. What’s your favorite way to spend a weekend?
  5. What’s something you’ve never done but always wanted to try?
  6. If you could change one thing about the world, what would it be?
  7. Do you think people are inherently good or bad?
  8. What’s your most unforgettable childhood memory?
  9. What’s the best compliment you’ve ever received?
  10. If you could have any superpower, what would it be and why?

Use These Questions to Spark Deep and Meaningful Conversations

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Asking the right questions is a powerful tool for creating connections. Whether you’re getting to know someone new or deepening an existing bond, these questions provide the perfect foundation for engaging, meaningful conversations. So go ahead—explore these questions to ask a guy and see where they take you!

Staff
Staff
FaithIt staff contributed to this article.

School Principal Slams Dad for Taking Kids on Family Vacation—& His Response Is Perfect

This dad responded to her salty email with pure class—and his points are pretty hard to argue with.

Grieving Widow Breaks Down Over 3 Men at Dutch Bros. Coffee Who Reached in Her Car Window to Pray

As soon as the young men heard about her husband, they extended their hands out the drive-thru window without a second thought.

Infidelity Doesn’t Just Happen. It Starts With 4 Subtle Warnings.

Here are the most important red flags and nonverbal communication channels you should be aware of...