280+ Interesting Questions To Ask Your Boyfriend Anytime

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Meenakshi Thakur
Meenakshi Thakur
The most creative person on the team, Meenakshi, adds colors to her content with new vision and ideas. She brings unseen insights to the content team with her 3+ years of experience in Digital Marketing. Apart from being cheerful and chirpy all day, she loves to explore the beauty of nature in her Biology laboratory.

Do you want to know more about your boyfriend? Are you looking for questions to ask your boyfriend without offending him? Then, the internet has made you reach the right place. Here is a bunch of questions to ask your boyfriend anytime without any worry.

Oh! It’s completely understood that, unlike others, some boys take a little more time to open up even in front of their loved ones just like an introvert. They might always answer your questions in a single line, or sometimes in a word or maybe two. Due to of which you might feel disheartened. After all, even after putting in a lot of effort, you are left with no particular output. But, not now!

No matter if you want to know about him or his past, you can use the opportunity and get to know your boyfriend more by asking him some questions. Some of the interesting questions to ask your boyfriend anytime are:

  • What is your biggest guilty pleasure?
  • What is your lamest skill?
  • Do you want to? (You know what I mean)
  • What is your idea of a perfect Sunday afternoon?
  • Have you ever had a dream about me?

Not enough questions? Is your heart craving for more such questions? Curious to know about them? Did you say yes? Then, keep up your curiosity and get to know about these exciting questions to ask your boyfriend below in the post.

Questions To Ask Your Boyfriend

Sometimes, you want to know about your boyfriend a little more, but don’t know how? However, you can ask some interesting questions as a game to get closer to him.

Here are some of the interesting, funny, trap, serious, cute, intimate questions to ask your boyfriend:

Funny Questions To Ask Your Boyfriend

Interesting Questions To Ask Your Boyfriend
Source: CTV News
  • Has anyone ever walked in on you in the bathroom?
  • What is the most embarrassing thing someone has caught you doing?
  • What is the most embarrassing moment you’ve ever had?
  • If you could legally change your middle name, what would it be?
  • Do you call your muscles “guns?”
  • What’s the most cringeworthy thing you’ve ever said to someone you were attracted to?
  • What is the funniest dream that you had that you can recall?
  • What’s the worst nightmare that you’ve had that you can recall?
  • Will you do your best animal sound for me?
  • Have you ever been streaking?
  • What about skinny dipping?
  • Do you want to?
  • What food do you love, but would hate as a Dairy Queen Blizzard?
  • What’s the food you like to have the most on your birthday?
  • What is your biggest guilty pleasure?
  • What was your childhood nickname?
  • What was your favorite thing to wear as a child?
  • Would you rather crank call or ding-dong-ditch your neighbor?
  • What cartoon character am I most like?
  • What movie is most like your life?
  • What is your favorite chick flick?
  • What is your favorite children’s book?
  • What is your silliest pet peeve?
  • What is your grossest habit?
  • Do you know how to spell antidisestablishmentarianism?
  • What is your lamest skill?
  • When your dog farts, do you leave the room or tough it out?
  • Where was the worst place that you had to fart?
  • How many selfies do you take a day?
  • Do you delete them or keep them?
  • Have you ever looked in the mirror and winked at yourself?
  • Do you ever talk to yourself in the mirror?
  • What is the cheesiest pickup line you’ve ever tried to use on a girl?
  • Did it work?
  • Have you ever been kicked out of a public place?
  • If you were a biker, what would your biker nickname be?
  • What is the best mode of transportation?
  • What’s grosser: Yellow teeth or yellow toenails/fingernails?
  • If there were a food that you absolutely couldn’t give up, what would it be?
  • What is your worst habit?

Also, Check 100+ Comments For Boys Pictures On Instagram

Deep Questions To Ask Your Boyfriend

Deep Questions To Ask Your Boyfriend
Source: OC Relationship Center
  • Do you want to have children?
  • How long was your longest relationship? Why did it end?
  • Have you ever been engaged or married? Do you ever want to get married?
  • Have you ever lived with a partner?
  • How important is religion or spirituality to you?
  • How do you feel about gay rights?
  • Do you think money can buy happiness?
  • What is your dream job?
  • What one thing do you want to accomplish in your life?
  • What accomplishment are you most proud of?
  • What are you afraid of?When was the last time you voted?
  • How would you describe your relationship with your family?
  • Do you have a best friend?
  • What is your love language?
  • Are you an introvert (those who recharge by being alone) or an extrovert (those who feel energized from being around other people)?
  • Do you hold grudges?
  • Have you ever struggled with addiction?
  • Have you ever been in an emotionally or physically abusive relationship?
  • Do you think a relationship can come back from cheating?

Fun Questions To Ask Your Boyfriend

Fun Questions To Ask Your Boyfriend
Source: Marriage Missions
  • If you had a pet unicorn, what would you name it?
  • OR if you could make any animal your pet, what would it be and why?
  • OR if you could become any animal, what would it be and why?
  • What kind of animal am I?
  • If you made up an ice cream flavor, what would be in it?
  • What would you call it?
  • You can only eat one thing for the rest of your time on earth. What do you eat and why?
  • Who was your celebrity crush as a teen?
  • Who was your real crush as a teen?
  • Who’s your current crush?
  • Have you ever watched really terrible children’s television just because you were bored?
  • What’s the worst movie you’ve ever paid to see?
  • Who are you most like, Michael Scott, Dwight Shrute, Andy Dwyer, or Ron Swanson?
  • Kill, screw, or marry: Miss Piggy, the flying dog from Never Ending Story, or Tweetie bird?
  • When was the last time you peed in the pool?
  • What about the sink?

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  • How often do you pee in the shower?
  • If you had a really fluffy bunny, what would you name it?
  • If you could give your bunny a super power of some kind, what would it be?
  • If you were a cartoon character, who would you be?
  • Would you rather be turned into a hologram or into 2-dimensions?
  • Nachos. What would you put on yours?
  • You have five dollars to spend on anything you want at the dollar store — what do you buy?
  • Name three random things. Just do it!
  • What are three things you can’t live without?
  • When you were a kid, what did you think being this age would be like?
  • What’s the grossest thing you’ve ever eaten?
  • What’s something you love that other people think is gross?
  • What is the most exotic thing you’ve ever eaten?
  • What’s the first thing that comes to mind when I say “Bruce Jenner?”
  • What’s the secret ingredient?
  • If you could do any kind of magic, what kind of magic would you do?
  • Finish this statement: “Look out! It’s a _____!”
  • If you were invisible for a day, what would you do?
  • What kind of superpower would you have if you had a choice?
  • What is the best organ?
  • What did you want to be when you grew up?
  • Have you ever pretended to be a woman?
  • Have you ever worn a dress?
  • Have you ever tried walking in heels?
  • Have you ever put on makeup?
  • Do you want to? (You know what i mean)

Cute Questions To Ask Your Boyfriend

Cute Questions To Ask Your Boyfriend
Source: Woman’s Day
  • Who was your role model growing up?
  • When you were a kid, what career did you want to have?
  • Did you go to summer camp?
  • What is your idea of a perfect Sunday afternoon?
  • What is your favorite holiday?
  • What is the best present you’ve ever received?
  • What did you and your friends do for fun in middle school?
  • Did you have any pets growing up?
  • What is your happiest childhood memory?
  • If you could cook any dish perfectly, what would you choose?
  • When you’re having a bad day, what makes you feel better?
  • At an amusement park, what ride do you just have to go on?
  • What toy did you always want as a kid, but no one ever bought for you?
  • Did you ever sleep with stuffed animals?
  • What sound do you love?
  • What are your favorite scents?
  • What candy do you hate?
  • What is your favorite karaoke song?
  • What was your favorite thing to do during recess?
  • What is your favorite thing to do on a rainy day?
  • If you could describe me with three words, what would they be?
  • Is there anything you dislike about me?
  • Does it make you smile when I send you a text message?
  • Do you think about me during the day?
  • What reminds you of me?
  • What kind of movie do you like us to watch together?
  • Do you think someone can be too much in love?
  • What was your first impression of me?

Also, Check 250+ What Would You Do Questions To Ask Anyone

  • If I was really sad, what would you do to cheer me up?
  • Do I make you want a future with me?
  • If I was scared, would you hold me?
  • Would you ever take me out on a picnic under the stars?
  • What is your favorite pet name for me?
  • What is a quirky thing about me that you love?
  • Do you get butterflies when you read my notes?
  • If I looked completely different, would you still love me?
  • Do you think I’m cute?
  • Do I look cute while working out?
  • If I was a dessert, what would I be and why?
  • How would you describe the way I smell?
  • What did you think to yourself after our first fight?
  • What kind of future do you see between the two of us?
  • Do you like to hold my hand?
  • Do you feel warm when we hug?
  • Do you like the way I walk?
  • Would you ever write a song for me?
  • Have you ever had a dream about me?
  • Would you risk your life to save mine?
  • Do you think I’m pretty?
  • Would you take my hand to dance, even if nobody was on the dance floor?

Trap Questions To Ask Your Boyfriend

Trap Questions To Ask Your Boyfriend
Source: PureWow
  • What do you mean by love?
  • How would you describe the perfect relationship?
  • What are you looking for or what do you most want from a relationship?
  • In your opinion, what does the ideal relationship look like?
  • What qualities should not a woman/man lack in order to be an interesting person?
  • What were the most heartbreaking things you did?
  • Where would you like to live?
  • What is your favorite place where you feel the best?
  • What is your biggest dream?
  • What holiday destinations do you prefer?
  • How do you imagine the future?
  • How do you think your life and career will look like in a year?
  • What or who inspires you?
  • Which is your favorite movie?
  • What are your passions or what is your biggest passion?
  • When you were a child, what did you dream of doing when you were old?
  • What are your favorite childhood memories?
  • What do you consider to be your greatest achievement so far?
  • What was the last concert you attended and why did you enjoy it?

Serious Questions To Ask Your Boyfriend

Questions To Ask Your Boyfriend
Source: Arizona Foothills Magazine
  • Are you a person who thinks negatively about a person, or has enemies, or holds grudges?
  • Where and how seriously do you see the both of us as a couple in five years?
  • Do you have any close female friends, other than me and any of your female family members?
  • Do you have feelings for any of your ex-girlfriends or a best friend whom you liked in the past?
  • Everyone has regrets about their past. Which is the one thing in your past you would like to change?
  • How do you think you would react if you found out I was cheating on you? (can be used as a truth and dare question to ask your man)
  • How would you find out or realize if there is no one more perfect for you than me?
  • If you found out that you were bankrupt one day with a family to fend for, what would you do?
  • If you plan to marry me, do you think you can manage a family in the future, financially and emotionally?
  • If you were given a choice, what would you believe in, God or Fate?
  • If my best friend bumped into you at the same club you visit regularly and made a move on you, how would you react? (if he says what you expect him to say, he’s definitely not being honest!)
  • If we ever have children, how okay would you be with me raising them according to my faith? (surely one of the serious relationship questions that you could ask your boyfriend, if you are considering marriage)
  • What are the experiences that have made you, who you are today?
  • What according to you is a perfect life, and how you would you try to make it for yourself and me?
  • What did you think of me, when we first met (be honest)?
  • Would you ever consider moving in together, and if you do, how comfortable would you be with privacy?
  • What do you think is the best quality in me, which attracts you?
  • What is that one thing in me, which you would like to change if given a chance?
  • If you ever got into a disagreement with any one of my family members or best friends, how would you deal with it?
  • Would you leave me for anybody in the world, including your family, friends, or anyone who has been closer to you in your life?

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Romantic Questions To Ask Your Boyfriend

Romantic Questions To Ask Your Boyfriend
Source: Travel Off Path
  • Do you feel when you are with me?
  • How do you feel when I kiss you?
  • What do you look or in a relationship?
  • What is the name of your favorite romantic movie?
  • What is your idea of a romantic date night?
  • What type of music do you like?
  • What color underwear do you like me to wear?
  • What sets the mood for you?
  • How do you like about my appearance?
  • What are the ways you like being touched?
  • What is your romantic dream place?
  • Do you like to cuddle?
  • When did you know that you were in love with me?
  • What is your definition of love?
  • What can I do to spice up our relationship?
  • Which intimate positions do you enjoy best?
  • Do you dream of me?
  • What are your dreams and aspirations?
  • Do you like sexy or smart?
  • Who is your celebrity crush?
  • What makes you smile?
  • What makes you shiver?
  • What makes you cringe?
  • What is your favorite color?
  • What actions do you find boring?
  • Which part of my body do you find attractive?
  • Do you get jealous when other men look at me?
  • What makes you jealous?
  • What makes you happy?
  • When you think of your future, what picture do you see?
  • What is your definition of a real woman?
  • Do you like my friends?
  • What makes you feel special?
  • What makes you feel calm?
  • What are your most important values in a relationship?
  • What is your favorite food?
  • How do you define a successful relationship?
  • What is your most favored memory of us?
  • Do I snore when I sleep?
  • Does my morning breath smell bad?
  • How many kids do you want to have in the future?
  • If you had to do it all over again, would you choose me?
  • What’s your favorite scent?
  • How can we make our relationship much stronger?
  • Do you like being affectionate in public?
  • What’s your favorite drink?
  • What reminds you of me when we are apart?
  • Do you like kissing, hugging, or cuddling?
  • Do you like jealous women?
  • Do you think that I really love you?
  • What do you fantasize about?
  • What is your worse secret?
  • Do you trust me? If you don’t, what can I do to make you trust me more?
  • Do you feel safe and secured with me?
  • Was it love at first sight when we met?
  • Who was your first love?
  • Does being in love make you happy or do you feel scared?
  • Has anyone ever hurt you in a relationship before?
  • When did you lose your virginity?
  • What’s your best and worst childhood memory?
  • Do you think I should stop asking questions?
  • Which do you prefer, talking or just sitting and relaxing?
  • What’s your best memory about high school and college?
  • What’s the one question you’ve been burning to ask me?
  • How angry have you ever been and why?
  • Do you believe that God exists?
  • Have you ever been obsessed with anything ever?
  • What’s the scariest thing that ever happened to you?
  • Have you ever had a pet?
  • What is the name of your all-time best friend?
  • What’s your definition of rich?
  • What’s the name of your first crush?
  • What’s your hobby?
  • If you could go back in time, what would do differently?
  • What’s the most rebellious thing you’ve ever done?
  • Do you believe in psychics and if so, have you ever been to see one?

Intimate Questions To Ask Your Boyfriend

Intimate Questions To Ask Your Boyfriend
Source: Crowdera
  • What is the first thing you noticed about me?
  • What role does physical attraction play in whether or not you pursue a relationship?
  • What type of scent do you like on a woman?
  • Would you say you have a “type”? Do I fit what you thought you were looking for?
  • How do you describe me to other people?
  • How do you think I should describe you to other people?
  • What could I do for you that I don’t do now?
  • What is the first thing you think when you see me?
  • What qualities make me special to you?
  • Do you look at other men (women)?
  • If you could have three wishes from me, what would they be?
  • What goals do you have for us?
  • What was the first thing you thought when you met me?
  • How would you respond if my appearance drastically changed, either overnight (new haircut and different hair color, for example) or over time (more/less muscle, weight gain/loss)?
  • What is something you think is true about me, but you’ve never asked to confirm?
  • How big of a deal are special occasions for you?

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Wrap up:

This was the list of more than 280 funny, intimate, serious, romantic, trap, and creative questions to ask your boyfriend. So what is the wait now? Call your boyfriend to play and get ready to receive some quirky replies. 

Wait! In the fun of asking questions, don’t forget to tell us in the comment section, which question among these questions to ask your boyfriend brought you the best laughter.


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