50 Amazing Questions to Ask a Guy post image

50 Amazing Questions to Ask a Guy

Breaking the ice with a guy you like can sometimes be challenging. It can also be tough to break past the typical flirty banter and really get to know each other.

I don’t know about you, but nothing is more painful to me (in a not physical pain sort of way) than awkward silences, especially on a date. And talking about the same old things can get tedious.

I started keeping a list of cool and interesting questions to ask a guy a while ago in an attempt to avoid awkward silences and generic conversation. Early on when I started dating my husband, we had a “questions” date night and it really brought us closer and helped us discover things about each other, and ourselves.

And with that, here are my top 50 questions to ask a guy you like to really get close. Some are silly, some are serious, and all will open the gates to a deeper connection and bond.

Ask Him These Top 25 if You Like Him

– These fun questions are lighthearted and fun. They’re a great way to connect, bond, and laugh.

1. What’s one thing you always procrastinate on?

2. What is the best way to end a long day?

3. If you inherited a billion dollars, what would you do with your life?questions-to-ask-a-guy-1

4. If you could choose one movie character to marry, who would it be?

5. What is your favorite quote or expression?

6. What is always worth the wait?

MORE: 5 Telltale Signs He Likes You

7. If you could only listen to one song for the rest of your life, what would it be?

8. How would you describe yourself in three words?

9. What would you immediately do differently if you knew no one would judge you?

10. What’s one thing you have never been good at?

11. What activities make you feel most like yourself?

12. What is your favorite childhood memory?

MORE: 10 Signs You’ve Found Your Future Husband 

13. Who would you cast to play you in the movie of your life?

14. If you woke up tomorrow with no fear, what would you do first?

15. What is your strangest pet peeve?

16. If you had to lose one of your five senses, which would you give up?

17. If you could make one wish, what would it be?

18. What’s something you’re glad you’ll never have to do again?

MORE: 20 Questions to Ask a Guy to Get Closer

19. What is one thing you’re most proud of?

20. What is one behavior that makes even the hottest girl instantly unattractive?

21. What’s the most embarrassing moment of your life so far?

22. Which do you prefer: a great book or a great movie?

23. Do you believe in soulmates?questions-to-ask-a-guy-4

24. If you could trade lives with one person for a day, who would it be and why?

25. What is the nicest compliment you’ve ever received?

Ask Him These Top 25 to Go a Little Deeper…

1. When making decisions, do you follow your head or your heart?

2. Would you rather be happy or successful?

3. What always makes you smile?

4. What always makes you angry?

5. What’s one mistake you will never make again?

6. What was the worst part of your childhood?questions-to-ask-a-guy-3

7. Does spending time with other people make you feel energized or drained?

8. What’s one thing you do as often as possible to feel alive?

9. What is something that happened this year that you are most thankful for?

10. If you could re-do one moment in your life, which would it be and why?

11. What will you never allow someone else to do to you?

12. How has your sense of right and wrong evolved?

13. What would your perfect day look like?

14. What has been the biggest blessing in disguise in your life?

15. When was the last time you had a good cry?

16. Do you believe love conquers all?

17. Is there anything you consider absolutely unforgivable?

18. What’s something you’re glad you’ll never have to do again?

19. What do you wish you could remember more clearly?

20. What makes you feel accomplished?

21. What is the biggest lie you’ve ever told?

22. What do you like most about yourself?

23. What is something you always look forward to?

24. What keeps you going during really difficult times?

25. Where do you hope to see yourself at this time next year?

If you loved this article, then check out these other must-see related posts:

50 Great Questions to Ask a Guy

How to Talk to a Guy and Make Him Like You

Break the Ice: How to Talk to Girls and Guys 

5 comments… add one

Leave Your Comment Now...


Oh gosh I realized I cannot ask 75% answers as I already know the answer 🙂 nice to realize 🙂

Reply October 5, 2017, 9:14 am


Love these! Definitely gonna try them out!

Reply September 26, 2017, 11:25 am


Love these! So deep and interesting.

Reply July 24, 2017, 10:09 am


what happen when you ask these kind of question and the man avoid answering . What does that tell you

Reply July 7, 2017, 1:13 pm


Hi! 🙂
I enjoyed reading this article and I had an idea
what if you share another article about different steps to prepare for the first date with a man? and what are the most important questions to ask ?
Thank you

Reply June 28, 2017, 9:09 pm

Leave a Comment


Sign up for our
free newsletter
and get a free chapter
of our book,"He's Not
That Complicated"