30 Fun & Deep What-If Questions To Ask Your Boyfriend & Have a Laugh

If you want to have a little fun, then you should try these what if questions to ask your boyfriend. Then you will learn a lot more about him!

what if questions to ask your boyfriend

You hear a lot of talk about not dwelling on the “what ifs” of a relationship because it’s not healthy to dwell on things that never happened or never will happen. Instead of telling you not to ask the “what if” questions to ask your boyfriend, we’re taking a different approach by helping you find the positive in asking questions that make you wonder.

What if asking these questions could ruin my relationship?

We wouldn’t be posting this if it was meant to challenge your relationship. The purpose of this exercise is to explore how you and your partner think. Each question is designed to reveal a positive answer that will make either one or both of you smile.

What if questions to ask your boyfriend

You might be worried about whether or not your boyfriend wants to answer these questions. Don’t worry. You don’t have to force him to respond. We’re only offering them as points of conversation to promote healthy communication and self-discovery. And now, without further ado… the questions. [Read: 60 get-to-know-you questions for a new romance]

1. What if you won the lottery and had enough money to change the world? How would you do it and why? 

Questions like these make you think about the responsibility of having a lot of resources, and what you can do to make the world a better place. It’s nice to know that people are thinking about the bigger picture, and asking something like this will give you insight into the causes that really matter to your boyfriend.

2. What if we were given the chance to go somewhere far away and beautiful? Where would we go and what would we do there? 

This question is meant to promote whimsy and wonder. A little lighthearted fantasy will do you both good—and who knows? You might end up planning a perfect vacation in the process.

3. What if you were given the chance to have dinner with your idol—what would you say to them and what favor would you ask of them? 

Each person should have at least one role model or person that they look up to. Asking this question will put a smile on your boyfriend’s face and give you a bit of insight into how much he admires his idol. [Check out: 36 racy, random, funny questions for flirty guys and girls]

4. What if we were forced to live in a zombie apocalypse? Where would we go and what would we do to survive? 

It’s an entertaining question that gives you a chance to bond over mutual interests—i.e. killing zombies. In this day and age, who isn’t planning their survival strategies, right? Also, this conversation could go all night long, which gives you enough time to cuddle and hash out strategies for blowing up brains.

5. What if teleportation was possible and also cheap? Where would you want to live, and where would you like to work? 

With a question like this, you can discuss infinite possibilities about where you want to live and what you’d like to do. People in long-distance relationships can benefit from a feel-good conversation like this one.

6. What if you could design your dream house without any financial limits? What would you put in it and why? 

This is the ultimate design-your-own-mancave question. Not only will it give you an idea of what your boyfriend is interested in, but it also gives him a chance to go crazy over what he would do if he could build his very own dream house. [Not a millionaire yet? Try: 17 brilliant, yet simple ways to save money as a couple]

7. What if you could choose to be one of the most famous billionaires in the world? Who would it be and why? 

There’s a lot of discussion going on in the news about what billionaires are doing and how they’re doing it. Your boyfriend has a lot of choices to choose from and his answer could give you a glimpse of how he perceives success.

8. What if you were born in a different era? Which would it be and why? 

Questions like this are always fun. There is so much room for imagination, yet at the same time, you must consider the impact of history on the people who lived in that era. As a bonus, it’s always fun to think of yourself in costume.

9. What if you could have any talent or skill in the world? What would it be and why? 

This could be an opener for a naughty joke, but it serves as a way to show a side of your boyfriend that he rarely considers. Some people are less likely to discuss skills they want to learn because they either don’t have the time or the confidence to try. [Not feeling particularly skilled? Read: How to stop being jealous of someone else’s success]

10. What if there were no wars on Earth? What would the world look like to you? 

Existential questions like this can really work the brain. It also helps you understand what peace and prosperity mean to a person you care about.

11. What if we were strangers now and you saw me in a different situation than when we first met? How would you handle it? 

Wouldn’t it be fun to know what else your boyfriend would do to impress you when you first met? Life could be different and it’s possible he wouldn’t try the same stunt to get your attention. And vice versa.

12 . What if we decided to quit our jobs and work as travelers? What would our jobs be? 

Of course, most people wouldn’t choose this as a way of life, but it is fun to consider what you think you guys are capable of when traveling the world on nothing but love and determination. [Check out: 8 tips to have a great time when you travel as a couple]

13. What if we spoke different languages and had no idea what the other was saying? How would you communicate your love for me? 

This question pushes you to focus more on body language and your actions toward each other. You will also learn how you choose to communicate without using words, and maybe even teach each other a thing or two about nonverbal communication.

14. What if you were the girl and I was the guy? What would you like to do that you never could as a guy? 

This is another interesting what if question to ask your boyfriend. A little roleplaying can make things interesting. Just make sure your conversation won’t tread on topics that may cause offense, like stereotyping and discrimination.

15. What if we were Jack and Rose, floating in the ocean with only a door as a floating device? How would you propose staying alive? 

The only wrong answer is to say that someone needs to stay in the water. Or you could choose to stay in the water together. Whatever the answer is, finding the solution will entertain you and may even give you some peace of mind about Jack Dawson’s fate in the Atlantic. [Read: 40 Casual questions to deeply get to know a guy you’re interested in]

16. What if we are really living in something similar to the Truman Show movie? 

This movie is about a man who is living in a TV show and doesn’t know it. He thinks it’s his whole reality, but there is so much more that he doesn’t know about. This gives you a chance to talk about the nature of reality and what you would do if you found out it was nothing like you think it is.

17. What if you found out that one of your loved ones or family members had committed a serious crime?

This is a deep question that will force the two of you to wrestle with your morals and convictions. What is more important to you? Being loyal to your loved ones or doing the right thing?

18. What if you had the chance to change history?

First, ask if he would do it at all. Then, if he would, what would he change and why? And would he do it if he didn’t know if the consequences would be better or worse? [Read: 87 Best dirty truth or dare questions for a wild and sexy night]

19. What if you could live forever?

Most people want to live to a ripe old age, but try imagining if you could live indefinitely. Would he want to do that if all of his loved ones continuously die throughout the centuries and millennia? You can also assume that everyone lives forever too.

20. What if you could re-do one single day of your life?

This will force him to look back on his life and some of the mistakes he has made. Ask him why he would want to re-do that particular day. What would he do differently?

21. What if you could read other people’s minds?

This might seem like a cool ability to have, but it would come with consequences. For example, you would know all the bad things that other people are thinking about you. On the other hand, it could give you an advantage in a lot of situations. Which would he choose? [Read: 196 Fun and deep questions to test how like-minded you are]

22. What if you knew that something terrible was going to happen to someone you love, but you couldn’t prevent it?

Talk about what he would do. Would he try to prevent it even if he knew he couldn’t? Would he spend more quality time with the person so that he would feel less guilt? 

23. What if you could take a time machine backward or forward in time? 

Try to ask him which period of history would he go back to and witness if he could – and why. Also, if he wants to go to the future, how far ahead would he like to go? What do you think the world will look like in hundreds or thousands of years? 

24. What if someone offered you $1,000,000 to stop showering for a year?

This is an interesting question because not only does it show you how much he values personal hygiene, but it also tells you how much he values money. Both are important, but which one is more important to him? [Read: 71 Friendly, funny questions to get to know someone in a happy way]

25. What if you were staying in a house that was haunted?

This is a good question to talk about his beliefs in ghosts or spirits. It also tests how brave he is and if he would risk the fear of staying in a house that is haunted by spirits that might make themselves known.

26. What if they created a cure for cancer but it would kill 10% of the people who took the drug?

You can talk about the pros and cons of this. On one hand, it sounds great. But on the other hand, losing 10% of the people who take it is a lot. What are the ethical implications? Or should everyone take it at their own risk?

27. What if you were abducted by an alien?

This question will get the two of you talking about the possibility of life on other planets or in other dimensions. And would he be scared if aliens took him to a spaceship or to their own planet? How adventurous would he be? [Read: 28 Awkward questions to ask a guy and weird, embarrassing ones not to]

28. What if you had a voodoo doll that could hurt someone without their knowledge?

If you are not sure how vindictive your boyfriend can be, then try this question. He might jump at the chance to hurt someone if given the opportunity. Or, he might be more ethical and say there is no one he would ever harm.

29. What if you could age in reverse?

Just like the movie The Curious Case of Benjamin Button, what would it be like if you were born old and got younger as time went by? Would you like to do that? What would be the advantages and disadvantages? 

30. What if you could shape shift?

Shape shifting is an alleged phenomenon that involves changing your form into something else. Think about the Twilight movies when Jake changed from a human to a wolf. Would you like to have this ability? And what would he change into and why?

[Next, read: 50 relationship questions to test your compatibility]

Do you think these what-if questions to ask your boyfriend can give your relationship a positive boost? Tell us how it works out for you in the comments!

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Danielle Anne
Those who can’t do, teach. I can neither do nor teach as well as others, but I can try. Aside from being a writer, I am also a physical therapist. My dream is...
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