Relationships

What if questions to ask a boy?

3 answer(s)
Answer # 1 #

Hey! As a guy who's been on both sides of these conversations, here are some "what if" questions that actually work well and don't feel like an interrogation:

For getting to know his personality: - "What if you could instantly become an expert in something - what would you choose and why?" - "What if you had to eat only one cuisine for the rest of your life?" - "What if you could meet any historical figure?"

For understanding his values: - "What if you won the lottery tomorrow - what's the first thing you'd do?" - "What if you could solve one world problem - which would you choose?" - "What if you had 24 hours to do anything without consequences?"

Just for fun: - "What if animals could suddenly talk - which species would be the most interesting?" - "What if you could create a new holiday - what would it celebrate?" - "What if you had to live in a different decade?"

The best approach is to mix serious and fun questions, and be prepared to answer them yourself too! It should feel like a conversation, not an interview.

[12 Day]
(2)
Answer # 2 #

"What if" questions are fantastic for getting to know someone better and having fun conversations! Here are some great categories and examples to ask a boy:

  • Fun & Imaginative Questions:
  • "What if you could have any superpower for 24 hours?"
  • "What if you woke up tomorrow as the opposite gender?"

  • "What if you could travel anywhere in time for just one day?"

  • Personal & Deep Questions:

  • "What if you had to leave your home forever and could only take 3 things?"
  • "What if you could change one decision you made in your life?"

  • "What if money was no object - what would you do with your life?"

  • Relationship & Values Questions:

  • "What if you found out your best friend was keeping a big secret from you?"
  • "What if you had to choose between love and your dream career?"
  • "What if you could instantly master any skill - what would it be?"

The key is to keep it light and fun, and really listen to his answers! These questions often lead to much deeper conversations than typical small talk.

Psychology Today has some additional great "what if" question ideas!

[13 Day]
(1)
Answer # 3 #

From a psychological perspective, "what if" questions are powerful tools for connection because they:

  • Reveal values and priorities without being too direct or intrusive
  • Encourage creative thinking and problem-solving
  • Create emotional intimacy through shared imagination
  • Break routine conversation patterns that can become stale

Some particularly effective "what if" questions for boys/young men:

  • "What if you could give your younger self one piece of advice?"
  • "What if you had to describe your personality using only three words?"
  • "What if you could master one skill overnight that would most improve your life?"
  • "What if you found out you had one month to live - how would you spend it?"
  • "What if you could instantly become fluent in three new languages?"

The magic happens in the follow-up questions - when he gives an answer, ask "why" or "tell me more about that" to deepen the conversation. This approach has been shown in relationship research to significantly increase feelings of connection and understanding between people.

[12 Day]
(0)

Related Questions