150+ Cute Questions to Ask Your Boyfriend

Author:
Tatiana
Updated date:
Feb 11, 2022 9:29 AM EST

Want to spark a deep conversation with your guy or just enjoy some cute Q&A? These questions can help the two of you grow closer!
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Spark a Conversation With Your Guy

New relationships are always fun and exciting, full of life and an undying desire to get to know one another. Once you’ve been together for a while, you become really comfortable with each other—and little things, such as the need to ask each other questions, begin to die down a bit.

Keep that spark going in your relationship! It’s totally necessary and shows that you are still interested in that “honeymoon” stage that is ultimately the beginning of a new relationship.

Why Intimate Questions Are Great for Couples

Asking questions is a fun way to get to know someone rather than trying to figure out the answers as you go. It's like a shortcut to learning anything you might want to know. And it's important to really know your partner—as psychologist Susan K. Perry says, "Intimacy is the sense of another person fully knowing you, and loving you because of who you are—as well as in spite of it."

Sometimes it’s just good to have a cute Q&A sesh, whether you’re really trying to get to know the boy on a more intimate level or you're just trying to be cute with one another! If you are in need of some cute questions to ask your boyfriend, here’s a whole list!

These romantic questions will get him talking about how the two of you got together and how you feel about each other.
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Cute and Romantic Questions to Ask Your Boyfriend

What does it feel like to you when we hold each other?
When did you first realize you loved/liked me?
What is your first thought in the morning when you wake up next to me?
If we got married someday, where would you want to take me on a honeymoon?
If I had to move away really far, would you come with me?
If I had to move away really far, would you stay in a long-distance relationship with me?
How do you feel when we’re apart?
Do you believe in love at first sight?
Do you believe in soulmates?
Do you think we’re soulmates?
Would you meet my parents?
Would you introduce me to your parents?
Would you shout my name to the world?
Everything happens for a reason—why do you think we met?
What was your very first impression of me when you first saw me?
What was your first impression of me when we actually met?
Do you remember the day we met?
What was the first thing you noticed about me that attracted you?
How would you describe our first kiss?
At what point did you decide that you wanted us to be “official”?
How did you know when it was time to say "I love you"?
Is there a song that you think of when you think of me?
Why do you like/love me?

These flirty questions ask about kissing, cuddling, and even skinny dipping.
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Flirty Questions to Ask Him

How many times did you want to kiss me before our actual first kiss?
Which do you like more: kissing in the dark or kissing in the rain?
How would you describe the way I kiss?
What is your favorite physical feature of mine?
What do you see when you close your eyes while kissing me?
Do you like to cuddle?
Would you braid my hair?
Would you rather hug for five seconds or kiss for one second?
Would you kiss me on the nose?
Would you kiss me on the forehead?
Would you hold my hand in public?
Would you kiss me in public?
Do you like when I touch your face?
Where is your favorite place to be kissed?
Where is your favorite place to kiss me?
Where is your favorite place to be massaged?
Would you ever go skinny dipping with me?
Would you ever take a bath with me?
Would you kiss me on the wrist?
Would you kiss me on the neck?

Cute Questions to Get Him Talking About You

If you could describe me with three words, what would they be?
What is your favorite pet name for me?
How would you describe the way I smell?
What's something I do (that I don't realize I do) that you love?
Is there anything you dislike about me?
What is a quirky thing about me that you love?
Would you ever write a song for me?
Would you ever write a poem about me?
Would you take a break from your favorite hobby to spend time with me?
Do you get butterflies when you read my notes?
Does it make you smile when I send you a text message?
Have you ever had a dream about me?
What is your favorite dream that involved me?
What is your favorite memory of me so far?
If I was really sad, what would you do to cheer me up?
If I looked completely different, would you still love me?
Would you risk your life to save mine?
Do I make you happy?
Do I make you want to reach your fullest potential?
Do I make you want a future with me?
Do you think I’m cute?
Do you think I’m pretty?
Do you think I look cute even when I'm a mess?
Would you take me out to see a chick flick?
If I was scared, would you hold me?
Do you think I look cute while I'm working out?
If we are watching a scary movie, can I cover my eyes and cuddle you close?
Would you take my hand to dance, even if nobody else was on the dance floor?
What kind of flower would I be?
Would you ever take me out on a picnic under the stars?
If I was a dessert, what would I be and why?
Would you give me a piggyback ride if my feet hurt?
What outfit of mine do you like the most?

Ask him questions about himself—you'll probably learn something you never knew about him!
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Questions to Get Him Talking About Himself

When you’re alone, do you think about me?
Am I the kind of girl you’d take home to your parents?
Do you have any secrets you’d share with me?
Do you talk about me when you’re with your friends?
If your friends told you to dump me, how would you react?
Would it embarrass you if I called you a pet name in front of your friends?
If you caught another guy trying to pick me up, what would you do or say?
Has a sad movie ever made you cry?
What is your ideal date?
If you have a vision of the perfect date to take me on, what is it like?
Do you prefer that I make the first move?
Do you mean it when you say you love me?
Does it mean a lot to you when I say I love you?
Does it make you feel good when I tell you how cute you are?
What is your fondest childhood memory?
How old were you when you had your first kiss?
On a date, do you prefer to watch movies at home while snuggling on the couch or to go out to the movie theater?
If I were to make you breakfast, what would you want it to be?
If I were to cook you dinner, what would make you the happiest?
Would you ever dress up for no reason and just dance with me anywhere, even an empty parking lot?
How would you describe your family?
Do you think your family will like me, too?
Would you enjoy going on a hot air balloon ride?
What would be your ideal vacation with me?
Do you let me win games?
If you didn’t win anything in a carnival game, would you try again?
Would you rather take me camping or on a tropical vacation?
Would you rather go on a road trip with me or with your friends?
Would you ever take me on a trip with you and your friends?
What things do I do that make you blush?
Would you prefer to lay on a beach with me to get a tan or get playful in the water?
When was a time that you laughed the hardest?
What’s the craziest thing you’ve ever done?
What’s the craziest thing you’d do for me?
Is there anything that I’d be surprised to find in your bedroom?
Who’s your celebrity crush?
Who knows you the best?
What’s your best feature?
What’s your favorite piece of clothing?
How can you tell that you’re going to be friends with someone?
What’s your favorite thing about traveling?

Deep Questions to Bring You Closer Together

Have you ever been in love before?
What does love mean to you?
What does being together mean to you?
What do you want out of being together?
What do you like about us as a couple?
What do you want to change about us as a couple?
What’s something you’re afraid to tell me?
What is something you want to know about me?
What do you wish I understood about you more?
How can we listen better to each other?
What, to you, is the most important thing in life?
Do you have any regrets?
What’s something that you want to change about yourself?
What is something I can help you with?
What is your biggest fear?
How do you know you’re doing the right thing with your life?
Would you change anything about your life, if you could?
When was a time you were deeply hurt?
What was one of the best moments of your life?
Tell me about your (best friend, parents, siblings). What’s your relationship with them like?
When do you feel appreciated the most?
What are your dealbreakers?

Intimacy is not a happy medium. It is a way of being in which the tension between distance and closeness is dissolved and a new horizon appears. Intimacy is beyond fear.

— Henri Nouwen

You might try starting the conversation with a few of these fun, random questions to get him talking!
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Random, Fun Questions That Will Help You Bond

If we were stranded on an island with no food, would you hunt to help us survive?
If there was only one cookie left, would you give it to me?
If there was only one cookie left, would you share it?
If you could feed me a dessert, what would you pick?
If I could be your passenger in any car or vehicle, what would it be?
Would you rather race me on a jet ski or have me on the back of yours?
What would the title of your autobiography be?
If you could have any kind of cake made for you in any size, shape, or color, what would it be?
You have three wishes from a genie. Go!
If you could go back in time, but only to last week, what moment would you visit and why?
Hotdog or hamburger?
Cookie dough or cookies?
Ice cream or milkshake?
Coffee or tea?
Sunrise or sunset?
You can only wear one thing for the rest of your life. What do you choose?
If you could choose to be talented with words, music, or dance, what would you choose?
What celebrity most resembles me?
If you could go anywhere right now, where would you go?
If money were no object, what would you have for breakfast every day?
Would you rather live in a cave or under the sea?
You just found five dollars on the ground. What do you do?
If you could throw anything against a brick wall, what would it be?
If you could pick a nickname for yourself, what would it be?
What would your catchphrase be?

So you really like this guy, and you daydream about him becoming your boyfriend. Ask some cute questions to get to know him better!
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Cute Questions to Ask a Guy You Like

Got a crush on a guy? Here are some questions you can ask to get to know him better and to make sure he's really the one for you. As the two of you bond, he may realize that he's developed feelings for you, too!

How long have we known each other?
When was your first crush?
How do you play it cool when you're around your crush?
What part of getting ready in the morning takes you the longest?
Which emojis would you use to describe yourself?
Which emojis would you use to describe me?
What was your first car?
What's one thing you really want to do this year?
What was the most fun thing you did last year?
What's the nicest thing you've ever done for someone else?
How many different places have you lived?
What's the funniest video you've ever seen?
Which dance can you do the best?
If you could be instantly good at anything, what would it be?
How would you spend a self-care day?
What is your absolute favorite meal?
If you were in a talent show, what would you perform?
What song do you know all of the lyrics to? (Bonus question: Ask him to sing it for you now!)
How do you usually ask someone out on a date?
Have you ever lied during a date?
What kind of personality are you attracted to?
If you were a . . .

car
shoe
animal
song
type of weather
color
food/drink
superhero

. . . which would you be and why? Which would I be?

The Q&A should go both ways! He might feel more comfortable answering questions about himself if you answer some, too.
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Let Him Ask You Questions, Too!

Even though you’re looking for cute questions to ask your boyfriend, the questions should go both ways! We all love to talk about ourselves, but making time to speak a few words about each other is a great way to rekindle sweet feelings in most any relationship!

Many of these questions are about you, so try to include some questions to allow him to talk about himself more, too, and expect to answer very similar questions if he is a willing participant in this Q&A.

Questions & Answers

Question: Why would you want to ask your boyfriend questions?

Answer: It's a fun way to get to know someone rather than trying to figure out answers as you go. It's like a shortcut to learning anything you might want to know. If you'd rather date someone indefinitely and wait to find out whether they're right for you or not, then you can also go that route.

Question: Should the guy pay for dinner during a date?

Answer: If I was going on the date, then absolutely. I'm not paying for the filet mignon and two lobster tails.