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30 Flirty, Fun Questions to Ask Your Boyfriend & Learn His Secrets


Sometimes asking silly questions can help you to get to know each other better. Not sure where to start? Try these 30 fun questions to ask your boyfriend!

There is nothing more fun than the “getting to know you” phase. If you feel like things have gotten somewhat stale and you’re running out of subjects to cover, fear not. These fun questions to ask your boyfriend can help you discover all the things that you don’t know about each other yet.

Whether you’ve been together for two months or 20 years, there are likely many stories that you haven’t heard that just take a little prying to get to. We all know how happy guys can be when they get to tell stories of their old days! These 30 fun questions to ask your boyfriend will get him thinking about a simpler time, laughing about the things he used to do, or even remembering the things that he felt the first time he laid eyes on you.

Fun questions to ask your boyfriend in a casual setting

Now, on to the fun questions to ask your boyfriend. The key here is to keep it light and to have fun with it. We all know that men hate being given the first degree, so make sure that what you’re asking won’t send up a red flag. Instead, you want to elicit a lighthearted, non-agenda response.

#1 What did you think about me when you first saw me? It’s funny when you think back to what your first impressions were of each other. He may have seen you and thought, “That is the girl I’m going to marry.” Finding out what it was about you that made him want to see you again might even help to spark some of those old feelings when things get a bit drab.


#2 Did you have an imaginary friend as a child? What type of friendships did he have? Was he a social butterfly, or more of the shy, silent type?

#3 Who was your favorite superhero? Every superhero has their own cool thing. What is it that he wishes he could do for the world?

#4 What was your dream car growing up? Was he all about the muscle car, the speed and sexiness of the Lamborghini, or did he simply want the new Mazda that his dad brought home in second grade?

#5 What is your most embarrassing moment? If he’s willing to share his most embarrassing and vulnerable moments when you ask your boyfriend these fun questions, you may gain some real perspective about who he is from those experiences.

#6 What is your greatest accomplishment? Find out what he values in life by asking what he thinks he has contributed the most to the world.

#7 What was your first memory? What are the things that stick with him? If he remembers only the terrible things, he is likely more of a pessimist. But if he remembers that he won a drawing contest, he may celebrate his accomplishments most. Or If he remembers the look on his mom’s face when she was happy about something he did, that may mean he is more sensitive than you think.

#8 Who was your first crush? The first crush a guy has can shape not only the women that he chooses in the future, but also the way that he enters a relationship later in life.

#9 What did you want to be when you grew up? We all wanted to be something when we were little, yet many of us don’t end up going through with it. Use this fun question to ask your boyfriend to find out what he wanted to be when he was young. This will even tell you whether he’s more of a pragmatist or if he’s willing to dream outside of the box.

#10 Did you like school? Some people thrive in a classroom environment, whereas others favor more active, hands-on learning. Find out which way your guy leans with this question.

#11 What was your favorite movie as a kid? Was he more of a fantasy guy, a slasher lover, or a regular comedian? What entertains him the most? Does he want to laugh, cry, be inspired, or be scared out of his wits?

#12 If you could have any superpower, what would it be? And would he use his powers for good or evil…?

#13 How long did you believe in Santa? How naive was he growing up? How long you believe in Santa not only speaks to the type of innocence he has, but it also says a lot about his gullibility and tender side.

#14 Did girls ever make you nervous? Was he a ladies’ man from the get-go or more of the silent observer type? Usually, a boy who is comfortable around girls remains that way. A man who’s more reserved may have a harder time communicating his feelings.

#15 Were you an early or late bloomer? Puberty is very unkind to most of us. If you grew really tall too fast, you felt awkward. Yet, if you were the runt of the group, you had something to prove.

#16 What was your favorite song in high school? Was he the Dead Head wannabe, the grudge guy, the Slim Shady, or the pop star? Music is very subjective, so this fun question to ask your boyfriend can say a lot about your personality style.

#17 Were you ever a momma’s boy? Momma’s boys normally don’t change. Even if he is one, if he can at least admit it to himself, chances are more likely that he’ll have a better handle on controlling relationship issues that may stem from this trait.

#18 What did you earn your first trophy for? Was he a super athlete, or did he earn his trophies by participation?

#19 Who taught you about the birds and the bees? Where did he get his information from about what a relationship is about? If he learned it from his parents, he likely got the whole “respect” talk. If he learned it in the locker room, he probably learned that it’s all about the “scoring.”

#20 When did you have your first drink? More adventurous people might have their first risk-taking behavior early on. If he’s still waiting for his first beer, then you know he doesn’t like to play with fire and does things by the book.

#21 Did you ever have a summer love? Summer loves are different from other types. They’re the ones that you fall head over heels for, throw abandonment to the wind, and blow your friends off for. Has he ever just let go and given all that he has to a short-term love affair?

#22 What’s your favorite meal? Is he a meat and potatoes kind of guy, or does he like a good soul food?

#23 What is it about a house that makes it feel like home to you? Does he feel attached to things and physical locations, or the people in them? If home is where his family is, he more easily bonds to people he loves. If home is an address, he considers home a structurally safe dwelling, regardless of the inhabitants inside.

#24 Was it hard moving away from home? Was he a homebody or someone who was ready to leave the nest and set the world on fire?

#25 If you could spend the night with anyone, real or fake, who would it be? Who is worthy of his time? If he could talk to anyone about anything, what knowledge would he want to gain?

#26 Who is your biggest hero? Is his hero someone they make comic books about, or his dad who puts on a suit every day and walks out of the door even when he doesn’t feel like it? Does he see spectacular in the everyday or in the extraordinary?

#27 When you’re gone, what do you want people to say about you? This is one of those fun questions to ask your boyfriend that’ll tell you a lot about the way he wants his life to turn out. What does he value in life and think is important to do while you’re here?

#28 Where do you see yourself when you are 70? What are his goals? Not just monetarily, but personally and emotionally?

#29 When will you think “I’ve made it”? At what point will he feel accomplished enough to say that he has everything he wants, that he couldn’t ask for anything more, or that he has done everything he’s set out to do?

#30 What is your best childhood memory? Does the memory focus around him and what he’s done, his friends and the time spent with them, or his family vacation that will live in his memory forever?

These fun questions to ask your boyfriend aren’t just for amusement. Sometimes a simple question can give you insight into a person that you may not get from just asking a question point-blank. Use them to get to know the real person deep down inside!

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