150+ Best Questions To Ask Your Boyfriend: Ultimate List 2023

Questions To Ask Your Boyfriend

Are you wondering what could be the best questions to ask your boyfriend?

For starters, before you arrived in your boyfriend’s life, he must have had awkward moments, great achievements, failed relations, etc.

Generally, guys do not open up when it comes to talking and conversation.

But you’ll need to ask a lot of the following questions as well or at least encourage him to give you more detailed answers.

Therefore, you need to know what questions to ask your boyfriend to learn about his past.

Here, I have gathered great questions to ask your boyfriend to give you both something to talk about while learning a little more about him.

Whether you’ve just started dating or been together for years, sure these questions can help you to create intimacy as well as to know your partner better.

However, I would suggest you choose questions you think will work best for your boyfriend and things you really want to know the answer to. let’s get started!

Cute Flirty Questions To Ask Your Boyfriend (to spice things up!) 2023

Cute Flirty Questions To Ask Your Boyfriend
Cute Flirty Questions To Ask Your Boyfriend

Getting to know your partner doesn’t have to be an interview or need to be serious. These cute questions to ask follow-up flirty questions to ask your boyfriend to make it a fun conversation or to spice things up.

“What is your love language?”

“What song would you compare our relationship to?”

“What was your first impression of me?”

“What’s your favorite memory that we shared?”

“If we had to spend the day together in one place, where would we go?”

“Do you like using pet names? Are there any in particular that you prefer?”

“Name three things that never fail to make you smile.”

“Do you prefer kissing, making out or hugging?”

“What do you think is your best feature?”

“How would you describe me in three simple words?”

“What is one thing that brings a smile to your face, no matter the time of day?”

“What’s one thing people would never know about you just by looking at you?”

“What does the idea of 4play mean to you?”

“So how did you get to become so hot/cute/adorable/handsome?”

“Did you know that you keep making me smile?”

“If you could a full 24 hours without any work or obligations, a day to just do whatever you wanted, what would you do?”

Related: Romantic Questions To Ask Your Boyfriend When You’re Bored

“For you, what are the cutest things to say to the boyfriend?”

“Do you think about me a lot?”

“What did you think when you first saw me?”

“Do you like romantic movies?”

“What’re your favorite cute ways to say goodnight?”

“Do you prefer to give or receive?”

“What’s the stupidest thing you’ve ever done?”

“Do you think you know what women want?”

“What’s the perfect way to ask someone out?”

“What emoji do you usually use when you’re flirting?”

“What’s the most romantic thing you’ve ever done?”

“What’s your favorite love song?”

“What do you think is my best feature?”

“Are you aware of how amazing you are?”

“What is something about you that would surprise me?”

“What’s the best joke you’ve ever told?”

Tricky Questions To Ask Your Boyfriend To Know Him Better 2023

Tricky Questions To Ask Your Boyfriend To Know Him Better
Tricky Questions To Know Him Better

“Which year of your life would you relive and why?”

“Does spending time with people exhaust you or do you love it?”

“What is something you consider unforgivable?”

“Do you believe things are meant to happen or that they just do?”

“Which qualities do you think a healthy relationship should have?”

“What’s something you’re glad you never have to do again?”

“What is something your other relationships lacked that was a problem for you?”

“What kinds of tasks do you procrastinate most on?”

“What’s the best way to end a long day?”

“How Would You Feel About Being With Someone Else?”

“What Is Your Ideal Relationship?”

“Do You Like Women Who Are Bigger?”

“If You Had To Choose All Over Again, Would You Choose Me?”

“Do You Find Someone At Work Attractive?”

Funny Questions To Ask Your Boyfriend To Make Him Laugh 2023

Funny Questions To Ask Your Boyfriend To Make Him Laugh
Funny Questions To Make Him Laugh

Sometimes it can be difficult to think of the fun questions to ask your boyfriend to make him laugh. Don’t worry, here are some funny questions that will get you laughing as well as help you strengthen your relationship.

“Is there anything you dislike about me?”

“Does it make you smile when I send you a text message?”

“What reminds you of me?”

“Do you think someone can be too much in love?”

“Do I make you want a future with me?”

“If I was scared, would you hold me?”

“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?”

“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?”

“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?”

“How often do you lie?”

“Who is your favorite celebrity”

“Tell me something about yourself that no one knows.”

“What was your most memorable event growing up?”

“Do you like hunting?”

“What is the most adventurous thing you have done?”

“What is the most expensive thing you have bought for yourself?”

“What is the most expensive thing you have bought for someone else?”

“What has been your wildest fantasy?”

“What would you do if your best friend told you I was bad for you?”

“Do you believe in an afterlife?”

“How special a memory is your first love to you?”

“Have you ever said, “I love you” and not meant it?”

“What was the craziest party you’ve ever been to?”

“Have you ever been jealous of either of your siblings?”

“Have you ever been jealous of your best friend?”

“Do you believe in soul mates?”

“Have you ever liked one of your best friend’s girlfriends?”

“How old were you when you started dating?”

“What word first comes to your mind when asked to describe me?”

“What word first comes to your mind when asked to describe yourself?”

“What are the qualities you hate in me most?”

“What do you think about a live-in relationship?”

“What was your first date like? Where did you go?”

“Are you afraid of ghosts?”

“Describe the worst date you’ve been on.”

“If a great-looking girl came up to you while I was there, what would your reaction be?”

“Are you addicted to anything?”

“What is the one thing about yourself that you hate the most?”

“Who is your favorite cartoon character?”

“Have you ever committed a crime?”

“When did you have your first crush?”

“Have you ever liked a teacher?”

Related: Romantic Questions For Couples To Know Your Partner Better

“Do you like being drunk?”

“When did you start drinking?”

“Have you ever stolen something?”

“What was the craziest dare you were ever given?”

“How many times have you been in love?”

“What is the worst thing you ever did to a friend?”

“If you are to lose one of your 5 senses, which one would it be? Why?”

“As a kid, which TV character do you have a crush on?”

“What is the craziest thing that you would do for me?”

“What is the craziest and the most beautiful gift that you have ever received?”

“Would you like seeing me in mini skirts and off-shoulder tops?”

“Do you discuss with your friends about our relationship and what we do together?”

“Would you like to enjoy a bath with me amidst the yellow and pink rose petals?”

“If I discover you lying to me, what will be your reaction?”

“Would you want to tattoo your skin for me”

Deep Questions To Ask Your Boyfriend That Will Strengthen Your Bond 2023

Deep Questions To Ask Your Boyfriend
Deep Questions To Strengthen Your Connection

When your relationship is getting serious, it’s important to know whether want this type of relationship or you have the same values, desires in life. The following important questions to ask your guy will assist you to understand him on a deeper level.

“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 one thing do you want to accomplish in your life?”

“What accomplishment are you most proud of?”

“What are you afraid of?”

“How would you describe your relationship with your family?”

“Do you have a best friend?”

“Are you an introvert or an extrovert?”

“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?”

“What makes you super happy in our relationship?”

“How long did you think our relationship would last when we first started dating?”

“What’s one thing you’re scared to ask me but really want the answer to?”

“What’s one thing that you wish I did more?”

“What are three key elements in a successful relationship?”

“If you were told you had a terminal illness, what would be three things you’d want to do?”

“How do you picture your life when you’re 60?”

“Would you surprise me with an expensive gift, or would you consult me before spending the money on it?”

“Do you think a proposal should be a grand public display or a private intimate moment?”

“What is something you did that you have regretted?”

“What are some things in life you had to learn the hard way?”

“Why do you think the divorce rate is so high these days?”

“Are you pro-choice or pro-life?”

“What’s one secret you’ve wanted to know about me, but have never asked?”

“If you could have chosen your name, what would it be?”

“If you could change one thing about yourself what would it be?”

“What’s your biggest insecurity?”

“How important is it for you to save money or invest?”

Lastly, here are some red flags you need to consider in your relationship with him:

  • His failures are always someone something else’s fault.
  • Unkind to animals or people for no reason.
  • He lies a lot about and doesn’t admit he lied when confronted.
  • People around you doesn’t like your boyfriend or warn you about him.

I hope these questions for your boyfriend help you to know him better as a person as well as a boyfriend/partner.

Moreover, check out these huge collections of questions to ask to help you make a list of follow-up questions to make your conversation interesting and fun.

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