Questions to Ask a Guy
Men are so uncomplicated that they verge on being complicated.
How do you really get to know a boy? Do you have to go through his things? Steal his phone and sleuth around? All ideas…
But if you’re less of the breaking and entering type, our list of the best questions to get to know a boy is the perfect place to start. Whether you’re about to go on a first date, building an old friendship, or simply curious about your sibling’s thoughts and interests, asking the right questions can open up meaningful conversations. From lighthearted topics to more thoughtful discussions, we’ve compiled a list of questions that will spark intriguing dialogue and help you learn more about his personality, hobbies, and values.
(We’re not responsible for the answers you may get in return).
- What do you think would shock the younger you most about the older you?
- What is something you really resent having to pay for?
- What is your hottest take about the differences between men and women?
- If you woke up in the body of someone of the opposite gender, what would you be interested to find out or do?
- Please explain in as much detail as you can how a woman’s cycle works.
- What is one thing you’re good at that people don’t expect?
- What is the smallest thing for which you are grateful?
- What do you respect most about your best friend?
- What do you think you do better than 90% of people?
- Do you feel like you are more or less memorable than the average person?
- In what ways have your political views changed the most over the years?
- What was most different about your life one year ago?
- How are you most different from the depiction of the stereotypical man?
- What three things are you looking for (or were you looking for) in a partner?
- What fact about yourself took you the longest to understand or accept?
- Who is your “hide a dead body” friend? (Note: not necessarily your best friend)
- What three person group would you have the easiest time road tripping across the country with?
- If you were limited to only three groomsmen / bridesmaids who would they be?
- Which of the five senses would you say is your strongest?
- Do you think you spend more or less time in front of a mirror than the average person?
- What was your sexual awakening?
- Do you think you are an above or below average dancer? Do you think you are an above or below average singer?
- What is your favorite free activity?
- What is something that gets cooler/more interesting the more you learn about it?
- If you could only save one item in a house fire what would it be?
- In what way do you consider yourself unique? (You can’t opt out by saying you aren’t unique)
- What stereotype fits you best?
- What is your favorite conspiracy theory?
- What is one thing that instantly makes your day better?
- What three things do we have in common?
- What percentage of the time have you kissed on the first date?
- Do you think men or women have a harder time going through puberty?
- How do feel about women asking men on dates?
- What is the biggest risk you ever took?
- What is your favorite board game?
- What was the most physical pain you have ever been in?
- What is the “strangest” thing you believe in? Do you believe in the supernatural? Heaven, angels, ghosts? Luck, fate, magic? Mind reading, lizard people, the Illuminati? Where do you draw the line of belief and disbelief?
- Have you ever won an award?
- What do you know isn’t real, but want badly to actually exist?
- If you could send high school you a one sentence message from current you (ten words max) what would it say?
- What aspect of health is easiest to you? Most difficult?
- What is something money related that you’re embarrassed to admit you don’t fully understand? (e.g. taxes, investments, mortgages, etc)
- What expensive thing is absolutely worth the money?
- What is your most irrational fear?
- When and where do you get your best ideas?
- What is the first thing you hope people notice about you?
- If you could only keep three apps on your phone, which would you keep? (Pre-loaded apps like Messages / FaceTime / calendars do not count towards your three).
- What was the last thing you read?
- How active would you say you are on social media? How do you approach social media consumption in your life?
- How do your beliefs inform your day to day life?
- What has changed the most about your palette in the last ten years?
- How important is the idea of “seeing the world” to you personally?
- How do you think we could handle disagreements better?
- What is the worst song you absolutely love?
- What are your unfiltered thoughts on Taylor Swift?
- What about being a guy do you think I would have the hardest time understanding?
- What hobby or interest that women have is the biggest red flag to you?
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