100 Questions To Ask Your Boyfriend: Build A Deeper Relationship

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Are you in a relationship but still feel like you don’t know enough about your guy? Here are 100 questions to ask your boyfriend so you can build a stronger and deeper relationship.

You can spend every waking hour with a person and still not know anything about them. You text each other regularly, go out for dinner and a movie. You’re always in touch, but what do you really know about your boyfriend?

Sure, you think inserting get to know you questions into regular conversation seems a little disingenuous. It’s just so scripted and fake,right?

Wrong. When you’re in a relationship, you have to put a little more thought into your conversations. Otherwise, years can go by and you’ll look back wondering if you actually knew anything about your loved one. It’s so easy to just talk about the unimportant stuff, without ever getting to the deep questions.

It’s not like you’re sitting down to dinner to ambush your boyfriend with questions. We’re just saying you can take this opportunity to ask a few things that will give you more insight into who he really is. It goes without saying that you have to be ready to be open as well.

Here are 100 excellent questions to ask a guy if you really want to know more about him. Of course, you have to pick and choose the questions that actually fit your boyfriend, and it’s very important to choose the right timing so you can get genuine answers. Don’t be asking random questions while you two are hiking, for example!

So, here are the questions to ask your boyfriend so you can build a better relationship.

#1 What’s the funniest thing you’ve done while drunk?

Drunken shenanigans are funny and almost everyone has at least one story. More importantly, this question sounds relatively innocent but can raise red flags if the guy you are dating is a little too wild or has way too many drunk stories.

#2 What’s your pet peeve?

This helps you avoid the things that really tick him off, and it gives you a little more understanding into his personality.

#3 What’s the one thing you can never eat?

There’s a story attached to this, so let him tell it! Maybe he had a really bad experience with spicy food once, or maybe he’s allergic to peanuts. Either way, it’s one of the most useful questions to ask your boyfriend.

#4 What’s the creepiest thing that ever happened to you?

We’ve all got that one weird story where you’re not quite sure if it’s something paranormal or mundane, but it’s one heck of an interesting yarn at least!

#5 What’s your guilty pleasure?

Is he a closet Kardashian fan, or maybe he’s into getting pedicures for self care? No problem. Men are often boxed into a rigid stereotype, so letting loose may mean doing some things that society isn’t that keen on. Let him share his guilty pleasures and become much closer in the process.

#6 What’s the dumbest expensive purchase you’ve ever made in your life?

Money is a major issue for any relationship, so letting him talk about his purchases and how he handles his finances is definitely a good idea.

#7 What language do you want to learn?

Is he interested in learning? Is he open to new cultures? These are great things to learn about a guy you’re dating.

#8 What’s the last book you read?

This question works whether or not he’s a big reader. If he is,you’ll learn about what genre he’s into. If he isn’t, you can at least make suggestions and start a mini book club.

#9 What’s in your bucket list?

Sure, it’s a cliche question, but why not give it a shot?Besides, you can take note of his response and keep it in mind. Part of being a good partner is being a good listener, and learning more about what he wants can make you a better match.

#10 What’s the most interesting fact that you know?

A lot of people have very interesting facts that don’t really fit into everyday conversation. This is his chance to share some random knowledge with you.

#11 What movie made you cry the hardest?

Men don’t cry — what a toxic mentality! Let him share what movie really touched him and left him crying. It will give you a lot of insight into what moves him and what issues matter to him the most.

#12 How many pets did you have growing up?

Is he a dog or a cat person? That’s not important! You just need to figure out what he thinks of smaller and weaker creatures. An animal hater is a red flag for any relationship.

#13 What relationship lessons did your parents teach you?

This question can tell you two things: what he thinks of relationships, and what his parents are like. That’s two bird in one stone.

#14 If you could drop everything right now, where would you want to go?

The rat race is tiring for us adults, and everyone has that one escape fantasy. Maybe it’s the Bahamas, maybe it’s some old cabin his family owns. Keep the answer in mind, though, so you could maybe fulfill his fantasy later on.

#15 What’s your happiest memory?

Talking about his happiest memory will get him reminiscing about the best moments in his life, and it’s very possible he’ll share details about the people who are important to him. It’s a great way to find out more about the relationships that matter to him and why they make him happy.

#16 What’s the most embarrassing thing on your google search history?

He probably won’t tell you about the worst ones, but it’s fun to talk about your search history. Be ready to talk about your most embarrassing ones, too, though!

#17 Who is your favorite One Direction member?

This is a joke to lighten the mood. It doesn’t have to be One Direction, just pick any boyband you can think of. If he gets annoyed and starts ranting about boybands, that could be a bit of a red flag. Who gets mad at some random fun question, anyway?

#18 What’s your worst travel memory?

Traveling is great, but it can yield memories both good and bad.What’s the worst thing that’s ever happened to him while traveling? This will help you figure out what sort of travels he’s into and how he handles a crisis.

#19 What’s your best memory of the first time we met?

This sounds very Rashomon, but we all have different angles of looking at and remembering certain memories. You may have your recollection of how your first meeting went, but what does he remember from that day? This question will give you some insight into his take on the relationship and what drew him to you.

#20 What do you want to ask me?

Yes, we’re talking about questions to ask your boyfriend, and this still counts. You want to get to know him, but this is a two-way street,remember? He has things he wants to know about you, too! Let him take the center stage and give him the opportunity to ask his questions.

#21 What’s the worst name and why?

We associate names with certain people and memories. Ask him about the name he hates the most and you’re bound to get a really interesting story about someone in his past.

#22 What’s the one thing you can’t live without?

Is it your phone? Is it your designer watch? His most prized possession lets you know what he values. If he can’t live without his phone,he’s a techie who has to be connected to everyone all the time. If he’s into his designer brands, that means he values how he looks and what this communicates about him. Make sure that you take these observations with a grain of salt, though. You don’t want to jump to conclusions and judge him over one small facet of his personality.

#23 Who’s your ultimate celebrity crush?

You’ve probably heard of the “freebie,” where partners give each other leeway when it comes to that one celebrity crush. It’s just a fun way to spark a conversation, and lets you get a little more insight into what he likes in a woman. Besides, you can use this as a starting point to push towards greater discussions moving forward.

#24 What’s the best music for a road trip?

Anyone who’s gone on a road trip knows that people can get touchy when it comes to music. Don’t take it too seriously, obviously, but it does show you what he’s into and what sort of music he enjoys.

#25 What’s your favorite workout?

Are you super into exercise? Then of course you want a partner who’s just as active as you are. Asking about his favorite workout lets you know what level of activity is regular for him, and whether or not he can keep up with you. It’s also a great way to figure out his opinion when it comes to health.

Those questions are bound to get a lot of very interesting and insightful answers, but you need more, right? Here are several more fun questions to ask your boyfriend so you can gain a lot more information. As with the earlier suggestions, make sure to tailor the questions to your specific situation.

#26 What’s your favorite time-wasting activity?

#27 What’s the best television show you could watch again and again?

#28 What’s that one unsolved mystery in your life that still bothers you?

#29 What’s your theme song?

#30 What is the one flavor you simply can’t stand?

#31 What’s the funniest memory you have with your sibling?

#32 What naughty thing at school did you totally get away with?

#33 Who was your favorite teacher growing up?

#34 What was your most memorable Thanksgiving?

#35 What’s that one weird thing you can do that no one else can?

#36 Who do you think is the funniest person ever?

#37 What can’t you quit?

#38 What do you collect and why?

#39 What unhygienic practice do you hate the most?

#40 What’s your budgeting style?

#41 When was the last time you played board games and what happened?

#42 Who’s your most annoying coworker ever?

#43 What’s the most nonsensical rule you’ve ever heard?

#44 What’s the one superstition you always follow?

#45 Have you ever been arrested? What for?

#46 What song do you have to dance to every time it plays?

#47 Who’s the one friend you can always count on, no questions asked?

#48 What are you most thankful for?

#49 What’s your worst nightmare?

#50 What’s the best thing you learned from your dad?

#51 Do you think recycling is actually useful?

#52 Who’s your favorite figure from history?

#53 What’s the craziest thing you’ve ever done at a bachelor party?

#54 What’s the most boring sport you can think of?

#55 What can you cook?

#56 How often do you check your phone?

#57 How many times do you call your parents each week?

#58 What makes you distrust a person?

#59 What’s the best gift you ever received?

#60 What is the greatest invention in your opinion?

#61 What is your go-to comedy movie for bad days?

#62 What’s your self care routine?

#63 How do you entertain yourself without gadgets?

#64 What was your first memory of the Internet?

#65 What’s the one food item you can eat every day?

#66 If you could have anything right now, what would it be?

#67 What’s the one thing you can’t forgive?

#68 What’s the worst betrayal you can think of?

#69 How do you show love without words?

#70 What’s the biggest deal-breaker for any relationship?

#71 What’s the funniest joke you know?

#72 Why did you break up with your last girlfriend?

#73 Do you believe in aliens?

#74 What scent brings back memories for you?

#75 If you could learn any skill, what would it be?

#76 Would you like to be a superhero, or would you rather be a villain?

#77 What’s that one music album where all the songs are excellent?

#78 What’s your craziest concert experience?

#79 How do you stay healthy?

#80 What’s the one topic you’re most passionate about?

#81 If you had to start a cult, what would be your first tenet?

#82 What religion were you raised in?

#83 What the most important political issue in your opinion?

#84 What charities do you support?

#85 What’s your policy on tipping?

#86 If you could be president for a day, what policy would you enact first?

#87 If you could have any animal as your pet, which one would you pick?

#88 What is the best thing you could do to cheer someone up?

#89 What turns you on?

#90 What makes a woman sexy?

#91 What is your perfect date?

#92 What secret would you like to share with me?

#93 What’s your favorite pizza topping?

#94 How would you describe yourself?

#95 What is the best vacation you can imagine?

#96 What do you think of marriage?

#97 What is the greatest expression of love?

#98 What are you willing to give up?

#99 What makes you feel loved?

#100 How do you envision our future together?

We know that these questions for your boyfriend range from the mundane to the very deep, but that’s the point. You can select the right ones depending on the timing and depending on the mood. Read them, figure out which ones can work for you, and pepper them into conversation when you have the chance.

Of course, you have to respect that it takes vulnerability for him to speak up,so be respectful of his responses. You have to be just as open and be willing to be vulnerable as well, for a deeper and more meaningful relationship.