15 What-If Questions To Ask Your Boyfriend to Grow Closer

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, 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 my boyfriend doesn’t want to answer these questions?

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.

#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.

#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, it also gives him a chance to go crazy over what he would do if he could build his very own dream house.

#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.

#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 means to a person you care about.

Now comes the juicy part…

#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.

#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? 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.



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