40 Intimate Questions to Ask a Guy

By on April 21, 2014

If you feel like you’re ready to dive deeper into your relationship with that special man in your life, check out these 40 intimate questions that will take your relationship from basic and casual to romantic and electric. (And who wouldn’t want that?)


1. What was the first thing you thought about me when you saw me?

Everyone wants to know what others thought about them during those crucial first moments. Did your man have a good first impression about you? Was he in love with your smile or drooling over something else? Perhaps he loved your funny personality or liked your rugged style.

2. What did you think of our first date?

First dates can either be magical or awkward. But no matter how it ended up, he obviously liked you enough to continue with the relationship. We still want to know the pros and cons though!

3. What is your dream date?

Make sure your guy gives you PLENTY of details. His dream date should be able to paint a beautiful picture in your head and really give you an idea of what kind of guy he is. You might discover a hidden romantic side you never knew about!

4. How many girlfriends have you had?

Let’s face it- this is just one of those questions every girl needs to ask her man at one point or another. And if you’re looking to make your relationship more intimate, now is the perfect time to throw this question out there.

5. Have you ever been in love?

This is another one of those questions us girls just have to know. And who knows? If he answers ‘no’, maybe you will end up being his first.

6. How much do you like me?

Because who doesn’t want to know, right? Plus this question will give you a great idea of how serious he considers the relationship and what he really thinks about you.

7. What’s your favorite thing about me?

I’m just going to tell you right now- this question provokes lots and lots of compliments- so obviously it’s a great one to ask (at any time). Find out what it is about you that drives him crazy. Don’t forget to flaunt that certain attribute extra hard from there on out!

8. What’s the one thing I do that turns you on the most?

A little bit romantic and a little bit steamy, this particular question will bring the two of you closer together and also let you know what you should be doing more of.


9. Where do you see our relationship in 5 years?

Is he in it for the long run? Who knows- but you’ll surely know after asking him this intimate question.

10. Do you ever want to get married?

This is definitely something you need to find out early on in the relationship- especially if the two of you are on opposite sides of the spectrum.

11. Do you ever want kids?

Some guys love little munchkins while others cringe at the thought. This is another important question to ask early on, especially if you’re thinking about following in the footsteps of the Duggar family and he wants to stay kid free.

12. I want to be the perfect woman for you. Is there anything I should change to make you happier?

Remember, he shouldn’t say anything about your appearance or who YOU actually are. But if it’s something like making him breakfast or being nicer to his mother, that’s acceptable.

13. Have you ever cheated on a girlfriend?

Clearly this deep question NEEDS to be asked early on in the relationship. If he says yes, run- even if he does have a ‘good’ reason for doing it. (They all say they had a good reason).

14. Is there anything you want to tell me?

This is a great way to just open up the conversation and make him feel comfortable enough to tell you something that’s been on his mind.

15. Is there anything you’ve done in the past that you can’t forgive yourself for?

If there is, tell him you’d be happy to help him make peace with the event so he can move forward with a clear and healthy conscious.

16. What time in your past would you love to return to?

Maybe he had an awesome teenage year he’d love to relive or maybe he’s happiest where he’s at right now. This is a great conversation starting yet simple question for your man!

17. What is your definition of love?

Everyone has a different answer to this particular question, so why wouldn’t you want to ask it?

large-218. Are you a religious person?

Whether you’re religious or not, it’s still good to know where your man stands on the subject.

19. When was your first kiss?

This is just a fun question to help get to know him a bit better.

20. How many women have you slept with?

You might want to know about your partner’s ‘history’. This could show he’s a player or you might discover you were his first!

21. What’s your biggest fantasy?

This intimate question is not only invasive, but totally fun too. Why shouldn’t you know your man’s fantasies? You might be in for a wild ride with this intimate question!

22. How long do you see us being together?

This is the perfect time for him to say ‘forever’. And really, if he doesn’t say that, I’d be a bit worried if I were you. He shouldn’t have a time limit for your love!

23. Would you still be with me if you found out I ________?

(You can put whatever you want there, like having a criminal record, not being able to have children, having a contagious disease, whatever you want). Let’s just hope your guy would still love you even under the worst circumstances!

24. What do you like about me the most?

Again, wait for the flurry of compliments! (We’re not complaining).

25. Would you still love me even if I got into a serious accident that ruined my physical appearance?

Your man better say yes. And no, it doesn’t count if he says he’d love you he just wouldn’t be attracted to you!

26. Have I ever hurt you in any way unintentionally?

Sometimes we do things that hurt our partner and we don’t even realize it! Now is the perfect time to clear the air.

27. Are you completely comfortable around me?

Your man should be so comfortable with you that he’s able to be himself and tell you everything. And if he’s not there yet, then work towards having an open and comfortable relationship to benefit the both of you.

large-328. Do you still have feelings for someone in your past?

If he says anything other than ‘no’, you might have a problem. Your man should be over his past relationships and focusing solely on you, or he might just be tempted to run back to his past girlfriend.

29. What is your definition of the perfect relationship?

Here’s a great way to find out what’s going on in that head of his. You might find out a few things that make you happy, or in some cases mad!

30. How often do you think couples should make love?

He might be silly and say something like every single hour, but in all seriousness- how much loving does your man really need to stay satisfied?

31. How do you feel about pornography?

People are really split on this topic. Some say it’s ok while others consider it cheating. Find out what your man thinks and see if your thoughts line up!

32. How do you describe me to others?

Your man should have nothing but wonderful things to say to you. But let’s find out what exactly he says to all of his friends and family members! Again, get ready for an influx of compliments.

33. How do you react when you’re in a situation that provokes anger?

Knowing the answer to this question is crucial and will help you learn more about his personality.

34. How did your last relationship end?

Another one of those questions that every female dies to know. It’s not only nosh, but will also let you know what things to be avoided during your relationship to make it work.

35. What’s your favorite thing that we do in bed together?

Whatever he ends up saying, do more of it!

36. What do you consider to be your greatest accomplishment in life?

This is really just an interesting question that will surely have an awesome answer that let’s you find out more about your man. Is learning his favorite song on his guitar his greatest accomplishment or has he done something a bit more notable like starting a charity or finishing his degree?

37. What will ruin our relationship?

Do we really need to explain why this is an important question to ask?

38. In your opinion, what’s the best way to show love?

This will let you determine when he’s showing you he loves you the most, and also give you an idea as to how to show him you love him.

large-439. How much time so we need apart?

Everyone needs time to themselves- for sanity purposes. How much space does your man need?

40. How can we make our sex life better?

Let’s just be honest here-men are driven by sex, so why not ask your guy how to keep him interested and spice things up. Remember, a bored man leads to a cheating man so make sure your man is constantly satisfied. Don’t forget to tell him what you need, too! (You’re just as important in this department don’t forget!)

Image credit: Madalina Mar, Valeria, Celia Y Laura, Myriam Porlier, and VegasUnicorn.