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

15 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 15 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.

If you’re looking for other questions to ask your boyfriend, just use any of these links to ask your boyfriend all the right questions you have in mind.

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

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