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150+ Freaky Questions to ask your Boyfriend

If your relationship is starting to get serious, it’s important to know if you and your boyfriend have the same values, desire the same kind of life. So the better way to know about your boyfriend is by asking him a question. So today’s edition is all about the Freaky Questions to ask your Boyfriend.

Guys can be notoriously closed off when it comes to talking and conversation, with lots of one-word answers. But here the questions we share are not for having a one-word answer.

Of course, there is no secret recipe for a happy relationship. But if we had to choose one thing, it would be a sincere and deep conversation.

As I already shared Cute Questions to Ask Your Girlfriend and today I will share  150+ Freaky Questions to ask your Boyfriend.

Freaky Questions to ask your Boyfriend

The fact is questions to ask your boyfriend come in different varieties, and have different purposes. So here I have managed the best possible types of Questions to Ask Your Boyfriend.

Sl No. Freaky Questions to ask your boyfriend
1 Do you prefer making out or cuddling?
2 What is the best kiss you have ever had?
3 What is your type?
4 Do you think about me when we are not together?
5 What is your opinion on a girl making the first move?
6 Do I make you nervous?
7 Have you ever had a dream about me?
8 What is your position on premarital S*x?
9 How important do you think S*x is in a relationship?
10 What do you wear to bed?
11 Have you ever thought about me sexually?
12 Where is your favorite make out spot?
13 Do I make you smile?
14 are you a shy guy, sexually?
15 Do you think you know what women want?
16 Who is your dream girl, if you couldn’t have me?
17 What part of my body would you want me to tattoo?
18 What outfits turn you on the most that women wear?
19 How many girls have you been with, before me?
20 What physical features are you attracted to the most in women?
21 Do you consider yourself more sexy or brainy?

Fun Questions to ask your boyfriend

Here are some questions you can try the next time you’re looking for something to talk to your Boyfriend about.

  • What fictional world do you wish actually existed?
  • What fitness craze, popular TV show, or other cultural phenomenon do you not understand?
  • When was the last time you sent a letter or postcard?
  • Do you ever laugh when you’re by yourself?
  • Would you rather go a day without your phone or without toilet paper?
  • What was the worst date you ever went on?
  • What fictional character do you wish was your best friend?
  • Would you ever go on a reality TV show?
  • What can you never have too much of
  • What is the lamest pickup line anyone has ever used on you?
  • If you were going to invent a cocktail, what would it be?
  • Have you ever won a contest or a raffle?
  • What is the funniest thing you’ve ever overheard?
  • Would you ever go to your high school reunion?
  • What is most embarrassing phase you ever went through?

Deep Questions to ask your boyfriend

Make sure you check the below Deep Questions to ask your boyfriend

  • 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 g*y rights?
  • Do you think money can buy happiness?
  • 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?

Cute Questions to ask your boyfriend

So here are the kind of cute questions you should ask a potential boyfriend.

  • When do you feel the most protected and taken care of?
  • What can I do to make sure you feel safe with me?
  • When we hang out with friends, do I make you feel like you’re still my priority?
  • When we are with my family, do I make you feel like you’re still my priority?
  • Do you have any deal-breakers, things that would make you seriously reconsider our relationship?
  • What was the very first thing you thought about me?
  • When did you first think I was attractive?
  • How long do you think people should wait before having kids?
  • What did you learn about marriage from your parents?
  • What did you learn about physical affection from your parents?
  • What is your favorite book?
  • What is your favorite song?
  • What was your first favorite movie, as a child?

Dirty Questions to ask your boyfriend

Here are some Dirty Questions to ask your boyfriend

  • What is your favorite part of my body?
  • You decide to give me a full body massage, where do you start?
  • What do you prefer: Boy shorts or stringy things?
  • Black lace or white t-shirt?
  • Would you rather see me in lingerie or nothing at all?
  • What is one thing that I wear that you find completely irresistible?
  • Have you ever just wanted to tear my clothes off?
  • Can you give me a good example of your dirty talk?
  • I ask you to dress me for our date night, which outfit of mine would you pick?
  • I catch you staring at me. What part of me were you looking at?
  • If you could see me wear anything, what would it be?
  • Do you get jealous when other guys check me out?
  • What is your favorite thing I do to you in bed?
  • Do you like when I make the first move?
  • When you first met me, was it love at first sight?
  • If you can describe my body with three words, how would you describe it?


Flirty Questions to ask your boyfriend

Flirty Questions are are cute to ask your boyfriend

  • How do you fight off procrastination?
  • What’s your jam?
  • How easily do you change your opinions?
  • What makes you feel alive?
  • What traits do you like about yourself?
  • If you could change one thing about your life, what would it be?
  • What is one thing that you wouldn’t change about your life?
  • What’s your favorite drink and why?
  • If you had to eat the same food for a month, what would it be?
  • Where would you live if money and work were not a factor?
  • Do you prefer to listen to your heart or brain when making important decisions?
  • What would you do if money and work were not factors?
  • Who is one person you wish you could be?
  • Who is someone you looked up to as a kid?
  • What’s the best piece of advice you ever received?
  • What is your biggest pet peeve?
  • If your life were a movie, what would it be called?
  • What is one thing on your bucket list?
  • Would you ever quit your job to travel the world?

Romantic Questions to ask your boyfriend

So, if you need some really great romantic questions to ask your boyfriend during a drinking game, Then these should be ideal

  • What’s the number one thing that you think makes a relationship last?
  • What do you love most about me?
  • What setting do you think makes the perfect date night atmosphere?
  • What physical action or gesture do you find romantic?
  • Who do you think makes a great example for a relationship and why? (Can be a celebrity couple or someone you know.)
  • What was your first impression of me when we met?
  • If you had your choice for a date night would you rather 1) stay at home and have a candlelit dinner, 2) Dress up and go to a concert, or 3) explore the great outdoors and go on a hike together?
  • What physical feature of mine is your favorite?
  • What’s your favorite way I touch you?
  • If you could travel anywhere in the world with me with no monetary restrictions, where would we go?
  • What song do you think of when you think of me?
  • Is there anything about me you might not know but want to know?
  • If you could describe me in only one word, what would it be?
  • What was your favorite part about our first kiss?
  • When and what was the first moment you knew you were in love with me?
  • What’s your most favorite outfit I wear?
  • What’s your favorite restaurant for date night?
  • What could I do to improve our relationship?
  • What about me first attracted you?
  • What’s been one of the funniest times we’ve had together?

Serious Questions to ask your boyfriend

  • What do you want to do when you retire?
  • Do you ever picture having grandchildren?
  • What’s another career that you think you would love?
  • What’s your favorite physical feature of your own?
  • Who was your favorite teacher when you were a child?
  • What’s your favorite memory with your mom?
  • What’s your favorite memory with your dad?
  • Which significant other before me had the biggest impact on you?
  • What did you think after your first sexual experience?
  • Did you like high school or college better?
  • Where have you always wanted to travel?
  • Did you ever consider a totally different career path?

Sexy Questions to ask your boyfriend

  • you get overly emotional about?
  • What event made you mature as a person the most?
  • What’s one thing that you’ve never told anyone?
  • What’s something you believe that most people don’t?
  • Is there anything you’re afraid of in life?
  • What’s your biggest regret?
  • Who is your favorite family member?
  • What’s the best way to earn somebody’s respect?
  • What’s your best memory from growing up?
  • What is your favorite thing to do in your spare time?
  • Who of your friends do you like to spend time with the most?
  • What was your favorite toy?
  • What makes life worth living to you?
  • What’s your favorite animal and why?
  • If you had to leave your house, what is the one thing you would take with you?
  • What tv show could you binge-watch all day?
  • What’s the hardest truth you’ve come to grips with?
  • What quirks does your body have?
  • What music do you like that you wish you listened to more?
  • How soft are you?
  • What are you a snob about?
  • What makes you the happiest?
  • What would it look like if you fully lived up to your potential?
  • How curious are you?

Good Questions to ask your boyfriend

  • What is your favorite memory of dating me?
  • What is your favorite sexual memory of us?
  • What food reminds you of me?
  • When was the last time you thought about me in a positive way?
  • What is your favorite thing that I do for you?
  • What movie reminds you of us?
  • Which of your parents are you most like?
  • Which of our kids are most like you? (or if you aren’t parents yet: Do you ever picture having kids?)
  • What’s my best physical feature?
  • What do you like most that I do in bed?
  • What’s your favorite time of day to be intimate?
Freaky Questions to ask your Boyfriend
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Final Words

Hi, myself Melinda Davis.Thank you for reading my article. I and my team put the best efforts to create this post to help You with the best choices. I think you got the perfect Questions to Ask Your Boyfriend.

We researched worldwide to get Freaky Questions to Ask Your Boyfriend. If You found this article valuable enough. I will love to hear from You. Let me know your thoughts about this post in the comment section below. Share the good words on Fb or Instagram.

Melinda Davis
Melinda Davis
Melinda Davis is a Licensed Marriage, Family & Relationship Therapist. She writes primarily about mindfulness, spirituality, and self-development and loves to share her knowledge about love, heartbreak, friendships, and relationships. Hit the contact form to get in touch with her.


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