20 Questions to See if He is Right For You


You’ve met a new guy and you really like him, but you want to make sure he is really what you’re looking for. Maybe he is the guy you could see yourself with or maybe he isn’t. Try asking him these questions to truly reveal if he is the one for you.

1. What is your first memory from childhood? 

This question will give you a glimpse into his mind and you’ll find out what things stand out to him.stock-photo-78151051-young-boy-and-girl-imagine-flying-on-skateboard

2. What is your favorite book and why? 

The kind of book he loves will say a lot about his personality. Does he love suspense fiction? Maybe he is the adventurous type.


3. What was your favorite topic to learn in school?

You can learn what interests him most by asking this question. If he says Phys Ed, then he likely loves sports. If Art was his favorite, he probably has a creative personality.

4. What is your most embarrassing moment?

He will surely have a great story and if anything, this question will at least get you laughing.

5. What is the weirdest thing you have ever eaten? 

This question could open up an amazing conversation. Maybe he tried crocodile when he took a trip the Gulf coast? Find out the story behind the weirdest food he’s ever tried.

6. What quality do you appreciate most about your best friend?

This is a great question to find out what he looks for in relationships. Is his best friend someone he can confide everything in? Then trust will be high on his list. Or maybe his best friend someone who he can let loose with? You’ll discover having fun is a priority for him.stock-photo-56424488-never-stop-the-good-times

7. Do you prefer tea or coffee?

Ask this one, and learn how he likes to have his drink. Maybe you can make it for him next time you’re together to show him you’re interested.

8. How long was your last relationship and how did it end?

You’ll want to know if this guy is going to be around for a short time or a long time. This question will gauge whether he is the relationship type.

9. What are the top five pet peeves that you have? 

We all have pet peeves. Learn what makes him tick by asking this one. If later you decide the guy isn’t for you, just pull out the knowledge of his pet peeves and implement them for an easy break.

10. What is your relationship with your parents like?

A guy who has a good relationship with his parents is likely to be a stable guy. If his relationship with his parents are not great, it doesn’t necessarily make him unstable, but it’s good to know his background so you can understand him better.

11. What current world issue bothers you the most?

Does he have issues with human injustice or with environment care? This is a great question to find out what he is passionate about.

12. If you could plan the perfect day, what would you do?

This will tell you if he enjoys the same activities you do, and maybe it will even help you plan a date!

13. What current goal do you have right now and how are you working towards it?

Find out if he is dedicated by asking this question. Does he sat out goals for himself that are never met or does he work towards them, completing them and setting up another?stock-photo-69131689-woman-writing-possible-with-brain-on-wall

14. What is the one aspect about yourself that you don’t like?

If he can share with you what he doesn’t like about himself, it will show he is able to be open and vulnerable. A guy doesn’t have anything to answer with might be arrogant and prideful.

15. If you could live anywhere in the entire world, where would you choose and why? 

Find out about his thirst to see the world by asking him this question. He might love fast-paced cities or the laid back feel of a low-key location.

16. Do you get bored a lot?

Will he look to you to entertain him or can he keep himself occupied? This is a good question to see what kind of guy he is.

17. What would you consider to be your dream job?

  This question will tell a lot about your guy’s personality and dreams for life. And maybe his answer will be similar to your dreams for life.

18. Has your heart ever been broken? If so, what happened? 

He is likely to have a story from his past. Ask this if you’d like to know the depth of his feelings when it comes to relationships and whether his past relationships have left him jaded.

19. Do you think physical and emotional intimacy are dependent upon one another?

  This is a telling question. Find out whether he is the kind of guy who just is looking to hook up or is he wanting something more. You’ll know right away if you are wasting your time or if things with this guy is going to go somewhere.

20. What value is most important to you in a relationship?

He might value kindness, or trust, or not being judgemental. This is a great question to see if you have the same values and if a relationship with him is going to work.