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80 Hypothetical Questions For Boyfriend

One of the best parts of being in a relationship is the way it lets you truly connect with your partner, not just through the usual surface-level chats but through those deeper, more meaningful conversations.

The ones where you feel vulnerable, open, and able to really share with each other. I had one of those moments not too long ago when my girlfriend and I were just chatting on the phone, catching up on life.

Then, out of the blue, she asked me a question that completely threw me off guard. It wasn’t anything trivial like “What’s your favorite color?” or “What did you have for lunch today?” No, this was one of those thought-provoking, “What if?” kinds of questions that make you stop in your tracks and really reflect on things.

I’m sure you know the type of question I mean—the kind that makes you look at your life, your choices, and your relationship from a completely different perspective. It wasn’t just idle chatter.

It was one of those moments where you realize just how much further you can go together in a relationship if you continue to ask those big questions. It was so much more than just talking about our day or exchanging pleasantries.

That moment of pausing and really thinking about her question felt special. It wasn’t just a conversation about the usual stuff. It was a conversation that went deeper, and I realized that, with each conversation like this, we get to understand each other more.

And that’s why I believe these kinds of “What if?” questions are so valuable—they challenge you, make you think harder, and help you connect in a way that’s truly meaningful.

So, if you’re looking for a way to take your conversations with your boyfriend beyond the usual “How was your day?” and dig a little deeper into each other’s minds, I’ve got a list of 80 hypothetical questions that can help.

These questions are a fun and thought-provoking way to explore different aspects of your relationship, your dreams, and your personality.

hypothetical questions for boyfriend

80 Hypothetical Questions to Ask Your Boyfriend

About Life and Choices

  1. Imagine you could live in any time period—what would it be, and why?

  2. If you could pick any superpower, what would you choose and how would you use it?

  3. Suppose a million dollars landed in your lap tomorrow—what’s the first thing you’d buy?

  4. If you could be famous for just one thing, what would it be and why?

  5. Where would you choose to live if you could live anywhere in the world?

  6. If you could change one thing about your past, what would it be?

  7. If you had to choose one career for the rest of your life, regardless of how much it paid, what would it be?

  8. Would you rather live forever or live a full, normal life? Why?

  9. If you could step into the shoes of any fictional character for a day, who would it be and why?

  10. If you could wake up tomorrow and automatically have any skill, what would it be?

Related: 20 Questions to Ask Your Boyfriend When You’re Overthinking

About Our Relationship

  1. What’s one thing you would want to change about our relationship, if you could?

  2. Imagine you could plan the perfect date for us—what would that look like?

  3. If we could hop on a plane right now and go anywhere, where would you want to take me?

  4. If you could see our future together, what would it look like?

  5. If you had to write me a love letter, what would it say?

  6. Is there something you’ve always wanted to ask me but haven’t yet?

  7. If you had to choose between living your dream job or being with me, what would you pick?

  8. What’s one piece of advice you’d give me for our future together?

  9. How would you sum up our relationship in three words?

  10. If you could spend a day walking in my shoes, what do you think you’d learn about me?

hypothetical questions for boyfriend

About Dreams and Ambitions

  1. What’s one big dream you have for your life that you want to achieve?

  2. If you could live anywhere in the world, where would it be, and why?

  3. If you could instantly master any skill, which one would you choose?

  4. If you could do anything you love without worrying about money, what would it be?

  5. If you could join any team, group, or organization, which one would you want to be a part of?

  6. If you could wake up tomorrow knowing everything about one subject, what would it be?

  7. What’s one thing about your life today that you’d change if you had the chance?

  8. If you could do something completely adventurous, what would it be?

  9. If you could live in a world where anything was possible, what would your perfect day look like?

  10. If you could start a completely new life, would you?

Related: 35 Odd Questions to Ask Your Boyfriend

About Personality and Preferences

  1. How would you describe yourself in just three words?

  2. If you could change one thing about your personality, what would it be?

  3. If you had to live without either music or movies, which would you choose?

  4. Who would you most like to meet—living or dead—and why?

  5. Imagine your perfect day from start to finish—what would it look like?

  6. If you could swap lives with anyone for a day, who would it be?

  7. If you could relive one day of your life, which one would it be?

  8. If you could choose one special talent to have, what would it be?

  9. If you had to settle in one city forever, where would you live?

  10. If you could be famous for something, what would it be?

Related; 261 Hot Seat Questions For Couples

About Fun and Adventure

  1. If we could go on an impromptu road trip, where would you want to go?

  2. If you could meet any celebrity, who would it be, and what would you ask them?

  3. If you could attend any festival in the world, which one would you choose?

  4. What’s the one extreme sport you’d try if you had the chance?

  5. If you could be on any reality TV show, which one would you pick?

  6. What food could you eat every day without ever getting tired of it?

  7. If you could visit any fictional world, which one would it be?

  8. If you won the lottery, what’s the first thing you’d buy?

  9. What would you do if you could walk in my shoes for a day?

  10. If you could be invisible for a day, how would you spend your time?

Related: 29 Romantic Pillow Talk Questions for Couples

About Future and Family

  1. If you had kids, what’s the first lesson you’d want to teach them?

  2. If we could live anywhere in the world, where would you want to settle down?

  3. If you could have as many kids as you wanted, how many would you have?

  4. What would your dream home look like?

  5. Would you be willing to live off the grid for a year, if it came down to it?

  6. If you could choose to never age again, would you do it?

  7. Would you be happy staying home as a stay-at-home parent, if that’s what life called for?

  8. What would you choose to do for the rest of your life, no matter the situation?

  9. What kind of legacy would you want to leave behind?

  10. If we had to move to a new city, what would be your first priority?

About Humor and Fun

  1. What’s the funniest thing you could say to make anyone laugh?

  2. Who would you prank, and how would you do it?

  3. If you could create a new holiday, what would it be, and what would it celebrate?

  4. If you could do stand-up comedy, what would your first joke be?

  5. What competition would you want to win, if you could?

  6. What would you invent if you could create anything in the world?

  7. If you could host your own talk show, what would it be about?

  8. What new law would you create if you had the chance?

  9. What’s the most perfect surprise you could pull off?

  10. If you could switch lives with a famous person for a week, who would it be?

About the Unexpected

  1. What’s one of your biggest fears that you’d want to face?

  2. If you could make any wish come true, what would you wish for?

  3. What’s something you’d do if you could do it without facing consequences?

  4. If you had to give up something important, what would you let go of?

  5. What moment in your life would you love to experience again?

  6. If you could make one impossible thing happen, what would it be?

  7. If you had to live without one sense, which would you choose to lose?

  8. What’s one thing about the world you’d change if you had the power?

  9. If you could help someone in secret, who would you help?

  10. If you could have one moment back, which one would it be?

Why These Questions Matter

These “What if?” questions, just like the one my girlfriend asked me, create an opportunity to dive deeper into your relationship.

They help you explore new sides of each other, challenge your thinking, and bring you closer together. Next time you’re talking with your boyfriend, try asking one of these questions. You might just find yourself learning something new and getting even closer than before.

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