115 Coolest and Cutest Question to Ask a Guy you like

Welcome! Oh, what brings you

here today? Oh is it that tall, white handsome guy again you’ve been stalking from the moment he walked past your college doors? Or are you one of those shy working lady at the office who tries to see the dashing new employee by knee-standing on the chair with your sneaky eyes over the cabin just to get a glimpse or last but not the least a girl with a simple crush on a guy while keep thinking about questions to ask a guy you like.

Well, worry not you girls! Behold. I know there is a mountain of questions that are piling up in your head right now and you wanna ask him. But you’re scared and overthinking is your mind does the most when it comes to situations like these!

What if he thinks I’m a despo?

Will asking that question makes me creepy?

Oh, I don’t wanna annoy him.

Oh is it too desperate to ask him for his number?

And the ton of other plenty questions that sneak up in your mind as the hour passes by. Girl, you need to calm down first. Take it slow and take one step at a time. Many of you think maybe asking too many questions isn’t the best way to know a guy, you might think as if you’re overloading “HIM”. But you’re actually not. Yes! Asking too many questions AT A TIME isn’t the best way.

There are ways of asking “too” many questions from a guy. You need to split your crazy questionnaire into junks and pieces. In this way, he’ll play along and won’t get irritated you from ever.

So without further ado, let’s get on with the questions!

22 Funny Questions to Ask a Guy

Well, I would definitely recommend to always starting with the funny questions. Guys love that! That piques their interest. Guys love simply love a girl with good sense of humor. So if you have that then girl you’re half way thru!

  1. What’s the most ridiculous/funny look you’ve worn?
  2. If you were Aladdin, what would you be three wishes from genie?
    (*Make yourself genie, to make conversation cute.)
  3. If you could be invisible for one day what would you do?
  4. Do you like to dance alone in the room?
  5. If I’m hung over and am banging on your door, would you let me in?
  6. If your favorite celebrity is coming to meet you but you get a common cold all of a sudden. What would you do?
  7. Would you get married in a church with someone you don’t like or be a runaway groom with the one you love?
  8. What is the dumbest thing, you have ever done in your life?
  9. Have you ever ringed a bell at someone’s door and run away?
  10. Are you really into me or pretend to be cool?
  11. If you were sitting next to your crush in your school, what would you say to her?
  12. How do you avoid embarrassing situations?
  13. Do you flirt?
  14. Would you go on a blind date?
  15. Do you snore while sleeping?
  16. Beer or vodka?
  17. Would you share your food with me?
  18. Do you iron your clothes?
  19. Selfie or group photos?
  20. Would you blind kiss someone?
  21. Were you always a perfectionist at flirting?
  22. If you were to get a piercing, where would you get it and why?

22 Random Questions to Ask a Guy to get to know Him

  1. Oreo shake or Ferrero shake?
  2. What is your Zodiac Sign?
  3. Do you like cats or dogs?
  4. What is your Favorite video game of all time?
  5. What is your Favorite movie?
  6. Where is 2nd favorite place to go in the world?
  7. How do you celebrate your birthday?
  8. Do you go to late night house parties?
  9. Who’s your best friend and why?
  10. With what kind of people do you get along easily?
  11. Do you have rules in your life?
  12. Were you a cool guy in high school or a nerd?
  13. What do you look in for a girl?
  14. How many siblings do you have?
  15. How many relationships have you been?
  16. How much makeup do you think a girl should wear on a daily basis?
  17. Do you like girls in high heels or flats?
  18. Would you want your girlfriend to be really stylish or a natural beauty?
  19. What’s the ideal height for a girl?
  20. How would you celebrate Valentines’ day?
  21. Would you go out for dinner with me in a fancy restaurant or order and then eat with me at home?
  22. Which season would you watch on Netflix?

16 Awkward Questions to Ask a Guy

Now the girls always can’t be sweet. Yeah, sometimes you lovely ladies ask questions that make your guy uncomfortable and feel awkward especially when it’s the start of your relationship. So hold your weird questions for some time and ask them away when you have gotten close enough to ask them openly when you know your guy won’t mind them at all.

  1. If I look ugly on a day would you tell me straightaway?
  2. Have you ever been dumped or have dumped other girls?
  3. Would you date someone who’s your grandmother’s age or someone your younger sister age?
  4. Are you a virgin?
  5. Have you ever had a threesome? If yes then with whom.
  6. Would you choose your best friend over me?
  7. When was the last time you went out with a girl and did the thing?
  8. If your girlfriend was in her “special” days would you still bone and do her?
  9. When will you take me to meet your parents?
  10. What is your job and how much is your income?
  11. When was the last time you had a hookup?
  12. Are you going to call me when I reach home?
  13. Would you like to have kids in future with me?
  14. When would we get married?
  15. Why did you break up with your ex and do you miss her now?
  16. Have you ever slept with another man deliberately or accidentally?

15 Interest Questions to Ask a Guy you have a Crush On

Ladies, it is very important to ask your guy some interesting information like the question. This makes him think of you as an intelligent girl and he likes you more then. You should know his favorite debate topics or the things he loves to talk about. A guy is really impressed when you have questions related to his favorite subject. Makes him feel more in control but it’s actually you who have the POWER!

  1. If you could read people minds, whose mind would you like to read first?
  2. Which movie do you think deserves a sequel?
  3. Which book would you read all day and never get tired of?
  4. What inspires you the most?
  5. Do you like to go to the gym?
  6. Do you read erotic novels?
  7. What is the first thing that you look in a girl?
  8. How would you define “perfection”?
  9. What would you eat every day and not complain?
  10. What matters the most in a relationship according to you?
  11. What gift would you like to get on your birthday?
  12. Can you carry your girlfriend handbags while she is shopping?
  13. What’s your favorite app?
  14. Do you believe in karma?
  15. What would you choose love or money?

10 Personal/Have you ever type Questions to Ask a Guy you Like:

  1. When was the last time you cried?
  2. Have you ever broken up and then get back with the same girl?
  3. Have you ever been in a bar and taken a girl back at home?
  4. Is there any disease you carry?
  5. Who do you like more from your parents?
  6. Have you ever slept with someone you don’t know and sneak out in the morning?
  7. Have you ever gotten into a fight because of your ex-girlfriend?
  8. Do you take your girlfriends to your home when your parents aren’t home?
  9. What is the regretful thing you have ever done in your life?
  10. Who would you ditch at the last moment when it comes to me and best friends?

20 Cute Questions to Ask a Boyfriend:


  1. What was the first thing you liked in me?
  2. If you were stuck on an island forever and you had one person to be with the island. Who would it be?
  3. What do you miss the most about being a kid?
  4. Would you make me breakfast on the weekends
  5. What movie will you only watch with me?
  6. Would you take me to prom in random clothes?
  7. How would you take care of me if I ever got sick?
  8. Would you say “I love you” to me every day?
  9. Would you like to wake up next to me every day or a single day next to Gigi Hadid?
  10. If you won the lottery, who will you tell first about it?
  11. Which stuff toy would you take with you to remind you of your girlfriend if you were away from her for a month?
  12. If it was our first anniversary, how would you plan the day for your girlfriend?
  13. Would you and your girlfriend wear the same outfit for a day and post pictures of yourselves on social media?
  14. What fictional character would you like to be?
  15. What was your favorite cartoon character when you were a kid?
  16. Where would you take me out on our first anniversary?
  17. What is the sweetest thing you have ever said to a girl?
  18. Which Disney princess do you think I am?
  19. Would you walk me to home?
  20. How would you make it up to me if I get mad at you?

There you have it, girls. Note these down or write down them somewhere or just ask them away! I’m sure you’re ready to cuddle and ask all of these questions from your boyfriend. Lastly, never forget he will love you for the way you are. Don’t change for him. Take care beautiful.

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