100+ Questions to Ask Your Boyfriend : A Complete Guide through 2017

By on December 19, 2016

When you’re in a new relationship things are so fast, exciting and fun. It almost feels like you will never run out of things to talk about with your partner. You could talk for hours and hours. However, the longer you date, the more the conversation can start fade away. It’s not usually because you don’t love each other, but because sometimes you feel a little less than stimulated. Once in awhile you just need to play a game of “20 Questions” to keep the conversation going. Not only do you need some stimulation once in awhile, but you might also find yourself searching for the things you and your boyfriend have in common with each other. This helps you learn if you’re truly compatible in the long run. Along with helping you identify your levels of compatibility, you will also find yourself bonding deeper with your boyfriend when playing q&a. Don’t try to get by on just the basic information on your partner. Dig down deep and get to know them in every way.  Get your conversation oiled up and back on track again by try out any of these following questions to ask your boyfriend:

20 Cute and Romantic Questions:

  • Do you believe in true love/soulmates?

In this day and age, most aren’t sure if true love is still there. By asking this question, you’re opening the door to interpretations of what true love means to both of you.


  • Do you think us meeting was fate or coincidence?

This is a great question to ask to get some theories rolling down hill. Surely you’ll both find yourselves entertained with the topic.

  • What did you think the first time you laid eyes on me?

Sooo cute! Obviously he’s going to say something sweet and you’ll share a beautiful moment together. Can’t you feel the love already?

  • Do you remember the first time you knew you loved me?

Hopefully he does! What an adorable question to ask. To reminisce with these memories will get you feeling all warm and fuzzy inside. We promise.

  • What are 5 things you love about me?

Every woman asks her man this question at some point in the relationship! If he can’t find 5 things, then he isn’t worth your time in the first place! He should love hundreds of things about you… 5 should be easy to come up with on his part.

  • What’s your favorite pet name to call me?

Perfect to ask when you’re establishing the names you will be calling each other. This way you can hear his preference and let him know if you dig it or not.

  • What is your favorite memory of us? Why?

It is crucial to ask the why part!! Don’t let him just tell you some generic memory without a reason. Have him reach deeper and find out his favorite moment you shared together. Then find out why is was so special to him.

  • Have you ever dreamed of me before?

We are thinking his answer will be yes.

  • Would you say you are happy being with me?

It’s important to find out if your boo is truly satisfied being with you. This question’s answer may not be smooth sailing… as in you may not always like his answer. By asking this your opening a gate that will give him an opportunity to gripe about anything he can think of. So, just be prepared for it.

  • Would you miss me if I left?

You can’t get much mushier than this question. This is prime to ask in the “honeymooners stage”.

  • What is something you would sacrifice for our love?

It’s an important thing to ask. Why? Because one day you two might find yourself in a sticky situation. One day something might call for sacrifices, whether from one or both of you. If he isn’t willing to sacrifice, even hypothetically, then you may encounter future problems with your relationship.


  • What would you do to cheer me up if I was really sad?

Get his answer so you can tell him if he is right or wrong. That way he knows how to actually cheer you up when the time comes. If he gets it right, he definitely earns brownie points!

  • Will you hold me close to you when I’m scared?

Who doesn’t love a sexy man who will protect you? We sure do.

  • Would you still love me if I changed bodies?

An extremely powerful question to ask your boyfriend. If there’s anything we are taught in the modern day and age, it’s how important looks are. Unfortunately, people forget there’s more than physical appearance to appreciate in a relationship. Hopefully he loves you for you and not just your body.

  • Do I motivate you to be a better person?

Do you see how romantic this question will be if he says yes? Don’t hesitate to ask your boyfriend questions like these. It will help the two of you figure out how inspire each other in the long run.

  • What do you picture us doing ten years from now?

Nothing is more romantic than commitment. Discussing your future will definitely keep the mood of love alive.

  • What song do you think describes our love?

It might take him a minute, but it’s worth the wait to find out!

  • What’s your favorite way to spend an anniversary?

Maybe he will give you some cute ideas for the future. 😉

  • Do you picture yourself having kids someday?

Although not every boyfriend may find this question as romantic. However, it’s definitely a critical question to ask in any serious relationship.

  • What do you think would be the perfect vacation with me?

Ahh, what’s better than daydreaming about a romance filled getaway with the love of your life?

20 Flirty Questions:

  • Are you a fan of public displays of affection?

The answer will let you know whether or not you’re able to kiss your babe the next time you two are out together. PDA does make some people uncomfortable, so it’s a nice question to ask to get his preference.


  • Where’s your favorite place to be kissed?

Whew! Is it getting steamy in here or is it just us? How much more flirty can you get than with this question to ask your boyfriend.

  • What turns you on the most?

If it was getting steamy before, it’s going to turn into a full blown sauna soon!

  • What’s the first thing you notice on a girl?

It could be he loved your eyes, your lips, etc. Whatever the case may be, this question always leads to large amounts of flattery. What’s more important than flattery when it comes to flirting?

  • How would you describe the perfect kiss?

Let him tell you, then you can show him how it’s really done.

  • What’s your favorite nickname to be called?

A great question to ask your boyfriend so you know if he likes that you call him honey bear or if he’d prefer something else.

  • Have you been working out lately?

The ultimate complement in question form! If this doesn’t make him blush then we don’t know what will!

  • Do you like it when I touch your hair?

If he tally digs you, then we are sure he won’t have a problem with it. However, asking is polite and can lead you both to run your hands through each other’s hair.

  • Do you like to be kissed on the neck?

*Fans self*

  • Would you kiss me on the neck?

*Wipes sweat off brow*

The flirt meter is off the charts with these types of questions!


  • What kind of dates do you like to go on?

Get an idea of what type of romantic antics he’s into with this cute question.

  • Do you like to cuddle?

Even though he’ll probably say yes, you’d be surprised at the amount of people who don’t like  to cuddle. Heartbreaking! We know!

  • What kind of making out is your favorite?

Is he a french kissing type of guy? You won’t know until you give this question a shot!

  • How many girls have you kissed before?

A tad bit personal, but everyone has a right to know their partners past! Maybe it’ll put you in the mood for some smooches, too.

  • Has anyone told you that you’re gorgeous?

Flattery is everything and this question is perfect to butter up your babe!

  • Are you a fan of dirty talk?

You probably couldn’t come off more flirty than with this steamy question.

  • Why were you ever even single?

One of the most important factors in flirting is building up the self esteem of your S/O. This question is perfect when you’re flirting with your boyfriend.

  • What’s your favorite physical attribute on me?

Now it’s his turn to build up your confidence. There is a more physical side to flirting so this is an awesome question to ask your boyfriend anytime!

  • Can I kiss you?

A little bold, but very much worth asking!

  • What’re you doing later?

Speaking of bold… Try out this perfect, yet straightforward question and see where it takes you.


30 Questions To Get Him Talking About You:

  • Do you still get butterflies when we talk?

By asking your boyfriend this question you will get him talking about you and only you. You’ll love hearing his answer and I bet he won’t mind telling you!

  • Do you like romantic-comedies?

You can change the genre on this one to fit you. (I.e: do you like horror films?) And then proceed to discuss your favorite movies.

  • Would you let me meet your family someday?

Ohhh, the big question… Second  to proposing that is. What is a better way to outline your future and get to know each other better than by asking about family?

  • What’s your favorite activity to do with me?

Questions like these will have you both smiling in no time. Plus it’s best to narrow down which activities he favors doing with you so that in the future you know what to suggest.

  • Do you think I look adorable when I’m doing something gross… Like working out?

We highly doubt he’d say that you look ugly,  but you’ll never know unless you ask!

  • Can you tell me my favorite color?

If you’ve been dating a while and need reassurance that he listens to you, then this is a excellent question to ask.

  • Will  you make me smile right now?

Put him to the test with this fun question/challenge!

  • Do you have any siblings? If so, what are they like?

Another way of getting to know each other’s backgrounds better. It will also give you an opening to discuss your family and siblings.

  • Are you a night or day person?

Everyone can relate to one more than the other. Which is he and which are you? Are you compatible?

  • Do you know my favorite movie?

We know it’s hard to pick one, but everyone has a favorite or at least a top 5 list. Let him take a guess and see how well he knows you.


  • What places do you love to eat at?

Who knows… Maybe you both share an undying love for that local diner downtown.

  • Do you prefer short hair or long hair?

We are not saying you should change your hair to fit what he likes, however now you gave a chance to discuss what you like on you and on him.

  • What’s your favorite food to eat?

Yes, these questions are meant to get him talking about you. But first you have to ask him to open up the gate for conversation.

  • Who is your greatest inspiration?

You can then tell him who your greatest idols are. We are fairly certain this convo could be  never ending.

  • Do you have an interest in art?

Maybe your boyfriend is the next Van Gogh. Or maybe he doesn’t know anything about art, but still likes to use adult coloring books for fun. Unless you ask you might never know how much you have in common in that area.

  • How much do you like/love me?

You can give him a 1-10 scaling option or you can have him just say “a lot” or “a little”. Either way it’s always fun to be reminded of his admiration for you, right?

  • Do you think I do a good job making you laugh?

A crucial topic to touch on so he can point you in whatever direction it takes to make him laugh more.

  • What are 3 things that you think make me special?

Everything about the answer to this should make you feel golden! It’s a perfect question to get him talking about only you… And only good things at that!

  • Will you call me on the phone sometime?

Don’t ask this question if you’ve already moved past a point where you’ve talked on the phone. If you haven’t already, then asking this will tell you where his comfort level is when it comes to calling.


  • Do you want to go out on a date with me?

Daring, but it will come off as adorable to him!

  • What music do you like?

Once you ask this, there is no coming back.  Talking about music could keep you two busy for days.

  • Do you have a favorite candy?

Who are we kidding? Everyone has a favorite candy! Discuss what both of yours are.

  • What movie do you think is the worst?

There’s going to be at least one movie he can’t stand. Maybe it’s the same as yours! This question is a great conversation starter.

  • How many people have you dated before?

Not everyone will want to discuss this type of info, so be cautious with it.

  • Do you see yourself dating more people in the future?

Yes this question is a trick question. His answer should always be no!

  • Do you want to be exclusive or in an open relationship?

Again, kind of a trick question. We hope he gets it right! Unless you’re into that kind of thing, of course.

  • How do you celebrate holidays?

What’s a better way to get him to light up than discussing how he spends the most treasured times of the year?

  • Where did you grow up?

Talking about your childhood is always a great way to keep conversation flowing.

  • What’s the worst date you’ve ever been on?

Nothing will get you more in the mood than reminiscing on the lame-o people you dated before. It will make the two of you feel so much happier being together!


  • Do you want to come over?

This one only really applies if you aren’t together at the moment. Also try to only ask if you really want him to come over!

40 Questions to Get Him Talking About Himself:

  • What’s your favorite place to go to get away from life?

Everyone has a special spot they turn to when they need peace and quiet. Sometimes it’s a park or maybe it’s their parents gazebo. Whatever it is, it will get him talking about something that means a lot to him.

  • Can you recall your most amazing childhood memory?

Everyone has embarrassing moments they can remember clear as day. However, great memories are hardly ever reflected on. Try getting him to open up to you by asking this question.

  • What is your favorite way to spend your birthday every year?

Who doesn’t like talking about their birthday?! Well, maybe there’s always that one debbie downer that’s always hating on that one day a year. But, if you get his answer you can use it to your advantage in the future.

  • Do you like coffee or tea more?

The dreaded question. Hopefully he chooses the same one as you! We’re just kidding. This question seems simple, but it can actually give you a lot of insight about your partner. Coffee drinkers tend to be a little more active and busy, while tea drinkers are a little more relaxed in their lifestyle.

  • Where do you see yourself in 5 years?

It’s always super important to get to know what’s on his upcoming timeline.

  • What is your dream career?

What we do for work isn’t always what we want to be doing. Asking him what he really wants to be doing is a great way to connect on a deeper level.

  • Can you describe your perfect woman?

This might be dangerous territory when it comes to protecting your own feelings, but it’s definitely worth asking.

  • What is your favorite food to eat?

Let’s just pray it’s not something like liver and onions. Yuck.


  • Do you like to watch/play sports? Which is your favorite?

A majority of the time (not all, but most) men like one sport or another. This question will definitely peak his interest.

  • What’s your favorite meal to eat: Breakfast, lunch or dinner?

Everyone has a favorite. And we mean everyone.  If they say they don’t, they’re lying!

  • What is your family like?

They always say that to get to know someone you should get to know their family. Well, they might not always say it, but we certainly suggest it.

  • What’s the best board game to play?

Maybe you both share a undying love for Monopoly. You’ll never know unless you ask!

  • Do you like to travel by plane, train or car?

How will you plan for you future road trips if you don’t know his personal preference?

  • What’s your bedroom look like?

This is an interesting question to ask someone if you’re in a new relationship and haven’t seen their bedroom yet. Looking at a person’s bedroom is like getting a tiny peek into their soul.

  • If there was one place in the entire world you could go to and live, where would you go?

A brilliant question to ask your boyfriend. Don’t forget to let him know your dream destination in return!

  • What is your favorite movie?

A must know for any couple in any relationship! Are you really dating if you don’t know their favorite flick?

  • Do you believe in traditional romance or a more modern one?

See if your beliefs match up by asking your boyfriend this question.

  • Who do you think should make the first move?

This question goes hand in hand with the previous one. It’s always a good move to ask him about his values.


  • What makes you smile?

Everyone should know how to make their partner smile, don’t you agree?

  • How do you spend your days off?

Maybe you both like to crack a bottle of wine (er, okay maybe a beer in his case) or a soda and just binge watch Netflix. Who knows!

  • What is your greatest strength?

This question will really give you a look at who your boyfriend is as a person.

  • What is your biggest weakness?

Now that you’ve asked his greatest strength, it’s time to dig into his weaknesses, too. This kind of information is good for building a stronger connection with him.

  • Have you ever been arrested?

Maybe he hasn’t. But, maybe he has and it will lead to a really funny story!

  • Does saying the L word intimidate you?

A perfect question to ask to get to know his intimate side. Sometimes men have a harder time saying gushy stuff like that. Unless you two have already verbally  professed your love for each other… Then just ignore this one and go to question #25!

  • What is the craziest thing you have ever done before?

There is never a time when a GREAT story doesn’t come along with this question. It’s an amazing conversation starter.

  • What was your first love like?

First loves are the worst right away, but then you grow up and one day find yourself laughing at them. A little bit of nostalgia never hurt anyone.

  • Do you have any allergies?

A critical question for any new couple. You don’t want to bring your man a pb&j surprise one day and not know it could kill, do you?

  • What’s your favorite social media site?

It’s 2017 already, if you’re not discussing social media at some point or another, you may not be real. Or at least we don’t think so!


  • Do you have any pets?

If he does own pets, you’ve just opened up a floodgate for him to gush about them for awhile! Every animal lover could talk about their fur-babies for days.

  • What do you think your spirit animal is?

A silly, but cute question to ask. His answer will also reveal how he perceives himself.

  • Can you cook? If so, what is your favorite thing to cook?

Ain’t nobody got time for a man that can’t cook, am I right ladies? JUST KIDDING! But, maybe you would like to know if you’ll be doing all the work in the kitchen or if you’ve caught a man that will serve you breakfast in bed. Either way, better find out by asking.

  • What is your favorite band?

Although he may have a die-hard love for rock and roll, his favorite band might be country. Ask him and find out how consistent he is.

  • Do you have any tattoos? If not, would you get any in the future?

Asking this question is good for trying to understand what personality type he is.

  • What’s your guiltiest pleasure?

It might take a little prying to get his answer, but you’ll be glad you ask.

  • Do you have a favorite comfort food? What is it?

How will you know if you both  eat a gallon of ice cream when you’re sad unless you ask him? You can also someday use this info to surprise him with his favorite treats. Essentially you’re collecting information to be the perfect girlfriend in the future! You can thank us later.

  • Have you ever met anyone famous?

This question always leads to amazing stories! You never know, they may have met some pretty interesting characters in their life.

  • What’s your sign?

Only ask this if you’re a believer in horoscopes. You’ll be entertained with the great conversation piece if you’re both into. If not you’re not then it’s pointless to ask.

  • What is your #1 goal on your bucket list?

Everyone has a list of things they’d like to do before they die. It makes for some interesting discussion when you ask your boyfriend what’s on his list.


  • If you could change one thing about yourself, what would it be?

A more intense topic to touch on. This may open up some doorways to viewing your partner’s greatest insecurities.

  • What are you religious beliefs?

If you haven’t already covered this base, now is a good time to start. Every couple should discuss their beliefs with each other.

20 Deep Questions:

  • If there was one thing you could eliminate from the world, what would it be?

Of course it’d be impossible to eliminate one thing entirely, but it is an intriguing question to ask.

  • What is your deepest, darkest fear?

Get to the really raw stuff by uncovering something deeply personal like your partner’s greatest fears.

  • What is your biggest regret so far in life?

We don’t think there is any deeper question than this one. Only due to the fact that it takes a lot of trust between two people for one to open up about their greatest fears.

  • If you could go back in time, which era would you visit and why?

A fun questions that will have the two of you daydreaming together.

  • What dead celebrity would you have dinner with if you could?

This is perfect as a dinner conversation topic. It’s laid back, but will both reflecting on both history and morality.

  • You find out you only have a week to live, who’s the first person you call?

A very sad, but thing stimulating thing to ask your boyfriend.

  • If you had one wish that could be granted, what would you wish for?

A great way to further uncovering who your boyfriend really is and what he hopes for the world.

  • Do you believe there is an afterlife?

An interesting topic to discuss when you’re reaching in the deeper parts of conversation.

  • What’s your philosophy in life?

Everyone has one!  Find out what his is and then tell him yours in exchange.


  • Are you an introvert or are you an extrovert?

An introvert is defined as someone who is shy and an extrovert is someone who is more outgoing. Everyone relates to one more than the other.

  • What do you think defines someone’s intelligence?

Not everybody has the same definition for intelligence. Not the literal definition, but just how they view someone as smart. It’s a great deep topic to touch on with your boyfriend.

  • What’s your experience with death?

Careful. This question is a little triggering sometimes. Death is never an easy thing to discuss. However, it does come up at some point in a relationship.

  • Would you say you’re guilty of “judging a book by it’s cover”?

Most people are, but maybe your honey is different.

  • If you could have one second chance to do over anything, what would you re-do?

You and your boyfriend will definitely be chatting for awhile if you use this one.

  • In your opinion, what person has made the biggest impact on humanity?

An intellectual subject for you to discuss.

  • How long do you think until human’s go entirely extinct?

A little morbid, but definitely interesting to talk about.

  • What are your thoughts on climate change?

Who knows, maybe you both have the same views!

  • Have you ever had an existential crisis?

An existential crisis is when you question the purpose of your life. It’s a philosophical subject, but not everyone has one.

  • Do you think machines will replace most humans in the workforce someday?

Ohhh, a very frightening, yet exciting thing to ask your boyfriend!


  • What are 3 things you wish the government would change?

Everyone has their gripes with their government. Get him a soapbox and just listen. Then tell him the 3 things you hope to see change, too.

20 Random Fun Questions:

  • Based off of my looks, what nickname would you give me?

Hopefully he answers this one gently and doesn’t tease you too much.

  • What’s a weird food combination you love, but other people think is gross?

Maybe he loves anchovies on his pizza or pickles with ice cream.

  • How far would you go to win a million dollars?

All boundaries are off with this random question.

  • What’s your favorite candy?

A silly and fun thing to ask.

  • Do you believe in ghosts and spirits?

Spooky. What’s more fun than discussing the supernatural?

  • Who is your celebrity crush?

Everyone has one, even if they won’t admit it right away.

  • If you were auditioning for singing competition, what song would you choose to sing?

This question might give you more info about your partner than you realize.

  • Do you like to do the Macarena?

This is literally the most random question you could ask, but it will have you laughing.


  • Is there a cartoon you have a crush on? Who is it?

Definitely a silly one to ask your boyfriend, but delightful all at once.

  • What is the most embarrassing habit you had when you were a kid?

Wouldn’t it be adorable if he used to cut his own bangs?

  • When did you get your first cellphone? What kind was it?

Everyone gets a good chuckle thinking about their first phone!

  • What would be your last meal if you were on death row?

Hopefully he will never actually have to choose. Still it’s a funny, random question to ask.

  • What two fictional characters would you choose to be stranded on an island with?

A mindless question but it’ll be so much fun to talk about!

Are you a believer in miracles?

Talking about miracles is always a fun thing to do. You and your boyfriend can compare the ones you’ve heard of and/or maybe seen! It’s a lot of fun, we promise.

  • When people are naked does it make you uncomfortable? Why or why not?

Definitely more than random we think.

  • Would you survive in the event of a zombie apocalypse?

Surely he has a secret plan thought up already, most boys do.

  • Have you ever peed your pants?

This question is the silliest!

  • Where is the weirdest place you’ve ever thrown up?

A strange thing to ask, but maybe it’ll lead to a great story.


  • Do you have any relatives locked up in the jailhouse?

Can you get any more random than with this one?

  • What were you parents going to name you if you were a girl?

A simple question if you’re looking for something light, but interesting to speak about.

Hopefully these questions do as promised and fulfill your journey to spark better conversation between you and your boyfriend. It may not always seem easy to keep things flowing smoothly, but it’s possible with the help of lists like these. Every relationship goes through dry spells with word exchange, but there is still hope. Don’t worry, you’ve got this!

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