Being in a relationship takes time, effort and above all, a desire to keep things fun and interesting. There’s few things more frustrating than a relationship that fizzles out simply because neither you or your partner took the time to nurture your connection with each other. (Watching television or playing video games together doesn’t count!)

Coming up with funny questions to ask a guy is a great way to keep your relationship fresh and exciting, and to learn more about him in the process. These 20 fun questions to ask a guy will not only help you put the thrill back into your partnership, but they will also let you see how his brain really works!

  1. “If you were given $100,000 and had to spend it all today, how would you do it?” 

Money isn’t everything, but learning how your man would spend a large chunk of it will help you to learn what he enjoys with no financial strings attached.

Sure, it may not be real money that he’s spending but his desires are. If you are looking for naughtier, dirtier questions, then try these.

  1. “If someone turned your life into a movie, which actor would you want to play you?” 

This question can give you an idea of who he idolizes, or what actor he thinks is most like himself. Other funny questions to ask a guy that are along the same lines include, “what author would you want to write your life’s biography?” or “would a movie of your life be a comedy, a romance, a horror flick or an indie drama?” 

  1. “Are you a cat person or a dog person?” 

Many people are essentially one or the other. Dog people tend to be more outgoing and playful, while cat people might be more reserved and quiet. Finding out which he is can give you clues to his true personality.

  1. “What is your funniest childhood memory?”

Getting him to share something special and funny from his childhood is a great way to get him to connect with you on a deeper emotional level. Keep it light. Asking what his worst childhood memory is doesn’t qualify as one of the funny questions to ask a guy. 

  1. “If you could be any animal, what would it be?” 

Animals have distinct personality characteristics, and he’s likely to choose one that either matches his personality or what he wishes his personality would be. Would he be a predatory feline like a lion or tiger? Or a sweet and cuddly kitten? His answer will clue you in about his most basic personality traits. 

  1. “If you could pick any actress to have sex with, who would it be?” 

Don’t get jealous over this one! He probably won’t ever have the opportunity. But this is one of the funny questions to ask a guy that can give you insight on what he finds super attractive in a woman. If you want to find out more of his sexual preferences, then you should try playing ‘Never have I ever’. These questions will get you started.

  1. “If you could visit any city in the world right now, which one would it be?” 

This is one of the fun questions to ask a guy that gets you both thinking. What if you could choose anywhere in the world and be instantly transported there, right this second? It’s an exciting thought for both of you. You could even have an entire date night sitting in the car imagining your trip to Montreal or Sri Lanka! 

  1. “If you only had one week left to live, what would you do?” 

This question is one of the deeper fun questions to ask a guy. He’s only going to list the things that are most important to him, or that he’s always wanted to do but never had the chance. His response will give you a peek into what really matters to him.

  1. “What is your least and most favorite food?” 

This may seem basic, but is one of the fun questions to ask your boyfriend that you absolutely have to ask. You definitely want to know what he likes to eat (and what he doesn’t) for later. Imagine surprising him with his favorite meal in a few weeks without him even asking!

  1. “Is there anything you’re really scared of?” 

Depending on where you are at in your relationship with your man, he may not respond to questions like this. But if he does, it can make him vulnerable to you in a way that he never was before and strengthen your connection with each other.

  1. “What is your deepest, darkest sexual fantasy?” 

If he feels ultra connected to you, he may share his ultimate sex dream with you. It may be something you’re surprised to hear, or something you’re not, like Princess Leia in the gold bikini. Either way, never judge him for sharing, even if it’s not something you personally are into.  For more on talking dirty to him, check out these dirty talking phrases.

  1. “If you could be invisible for a whole day, what would you do?” 

He might say that he would visit a strip club or a lingerie store. Or he might give you an answer you totally never expected! This is a one of the funny questions to ask a guy that could have you both laughing.

  1. “If you could go back in time, where/when would you go?” 

This question will give you an idea of what the most important event in his past was. It could also open up the conversation for something that hurt him in his past, or something he regrets. Remember to be supportive if he chooses to share something intimate as opposed to funny.

  1. “Describe yourself in only three words.” 

Want to get him to tell you what he really thinks of himself? Give him only three words to do it in. It’s one of the funny questions to ask a guy that will really get his mind going and get him to reveal more about his personality and how he sees who he is as a person.

  1. “If someone could read your mind right now, what would they hear?” 

This is one of the fun questions to ask your boyfriend that has the potential to be really funny, or really serious. Either way, don’t you want to know what he’s thinking right now, while he’s with you? Accept his candid answer without argument, whether it’s something that makes you happy or totally freaks you out. 

  1. “If you could commit a crime and never be caught, what would you do?” 

Let him reveal his bad boy side for just a moment with this question. Would he commit murder to get back at someone he hates? Or would he steal the crown jewels just for you? Don’t judge him on this answer — he’s not actually going to do it. But it can be fun to pretend for a few minutes that he has the freedom to do any bad thing he wants!

  1. “Describe your dream house.” 

This is one of the fun questions to ask your boyfriend that gives you some insight on how he sees his future. Does his dream house include a wet bar and a game room? Or a nursery and a peaceful garden? His ultimate house can give you a clue on what is important to him, and where he sees himself in the years to come.

  1. “If you were alone on an island, how would you get off?” 

Guys love to strategize. Get the gears in his mind working with this cool question! You might be surprised at how creative and clever he gets with his answer. Similar fun questions to ask a guy might include, “if you were trapped in a sinking ship, what would you do?” or “if you were a military general about to declare war, what attack strategy would you use?” 

  1. “If you could be anyone for a day, who would you be?” 

This question will give you an idea of who he idolizes, or whose life he envies. He might want to be Bill Gates, or he might just want to be a doctor overseas helping underprivileged children. Either way, the answer gives you an idea of what he strives for.

  1. “If you could do one thing to save the world, what would it be?” 

Get your man in an altruistic mood by asking him this question. Would he stop global warming? Abolish corporate lobbying? End world hunger? This question is a fun one that will also give you both ideas about smaller things you can do to make a positive impact on the world around you.

Coming up with unique and fun questions to ask a guy not only helps you learn more about him, but also gets your imagination going. These fun questions to ask your boyfriend will give you a deeper look into who your man is as a person, and what his goals and dreams are in life. Learning more about him in this way can help you to connect on a deeper level, and keep your relationship fresh and exciting. Just remember, he may very well ask you the same questions! Make sure you’re ready to answer too. 

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