If there is a certain guy that you want to get to know better because you are interested in him in more than just a friendly way, there are a lot of great questions you can ask. The following questions will help you figure out whether or not he is relationship material. The better you get to know him, the easier it will be to decide whether or not to make your move.

1. What are you most passionate about in life?
This is a good question to ask because it sort of shows you what his priorities in life are like.

2. Where do you see yourself in 5 years?
If you want a man who knows where he is going, this is a great question to ask him.

3. What do your consider your biggest accomplishment?
This is another excellent question that will tell you how motivated he is and what he has already done with his life.

4. What do you look back on most fondly from your childhood?
The kind of childhood that he had plays a part in the kind of man he is now, so it’s an important thing to know.

5. Are you close with your parents?
It’s always good to find a man who is close with his parents/family. Ask him which parent he is closer with as well.

6. What do you fear most in life?
The answer he gives to this question can say a lot about him as a man, but it also opens up the opportunity for levity.

7. What is something you’d never want your family to learn about?
You definitely want to know about some of his deeper secrets before deciding whether or not to date him.

8. What is your ideal version of life like?
If you want to know if you’ll be compatible with him in the long term, this question is key.

9. How important is money to you?
This is another good question that is about priorities, and his answer could indicate just how greedy he is.

10. What is the dumbest thing you’ve ever done?
The answer to this question might surprise you, and you’ll certainly gain some valuable insight.

11. What are you deepest regrets?
We all have regrets in life, but the ones he has will tell you something important about him as a person.

12. What was your first kiss like?
The way he describes his first kiss could tell you how much of a sentimental person he is.

13. How many girlfriends have you had?
The number of girlfriends he has had could be a good thing or bad thing, depending on the answer. Too few means he’s inexperienced, and too many could mean commitment issues.

14. What turns you on most about a woman?
When you get the answer to this question, you will know what to focus on to make yourself more attractive to him.

15. What is your biggest turn off?
If he answers and describes something that obviously applies to you, it probably isn’t mean to be. This can be a good way to quickly figure out if it’s a match or not.

16. What is the toughest emotional experience of your life?
Learning about some of his emotional scars can give you some great insight into him as a person, and it can lead to some deep bonding.

17. If you won a million dollars today, what would you do with the money?
This question will tell you just how responsible he is. Would he invest a large portion of the money or just blow it all on a big house a garage full of cars?

18. What is one of your guilty pleasures?
Everyone has their guilty pleasures, and learning about his can bring you closer together. Maybe you even share some of the same ones!

19. What is your perfect first date like?
If he lays out this really nice image of a first date that really appeals to you, there could be fireworks. If he’d prefer to go to McDonalds, you’ll probably want to walk away.

20. Do you want to have children?
This question might seem a little person or straightforward to ask a guy you don’t know very well, but in the context of a question game it won’t come across as very strange. It will also show if you are compatible in an important way.

21. Who is your role model?
The person that he most looks up to will really give you a good look at what his overall character is like.

22. If you had to describe being in love, what would you say?
This question is another opportunity for you to find out just how sensitive he is, and whether or not he’s ever really been in love.

23. What is one thing about yourself you’d like to change?
It’s always important to know about the things that he doesn’t like about himself.

24. Are you a morning person?
If you ever end up living with him, it’s probably a good idea to know whether or not he’s a morning person.

25. What is most important to you in a relationship?
You will find out what really matters to him most in a relationship, which will show you what kind of partner he would be.

26. Are you a superstitious person at all?
This question can spark some interesting conversation if the answer is yes.

27. Have you ever been arrested?
Probably a good idea to know whether or not the guy you are interested in has a record.

28. What subject in school interested you most?
Another great question to encourage conversation, and you’ll learn if he is an intellectual type.

29. What kind of music do you like?
You don’t necessarily need to love the same music, but it’s a great thing if you share this in common.

30. If you could have any job, what would it be?
This will tell you what kind of a person he really is deep down and what he passionate about.


Anna Perkins is a relationship writer who offers her own forthright opinion over the worlds of dating, romance, relationships , marriage and friendships. She loves cats, traveling, spending time with her son and husband.

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