40 Personal Questions to Ask Your Boyfriend

By on October 8, 2014

personal questions

Sometimes, it’s difficult to come up with new questions to ask your significant other. It’s not that you don’t want to know everything about him, it’s that you can’t think of anything you don’t know. Find out some home truths about your partner-and about yourself-with our handy list of personal questions to ask your boyfriend.

1. When was the first time you said “I love you”?

It’s interesting if nothing else to find out when your partner first said those three magic words, and who it was he said them to. You might find yourself surprised.

2. When was the first time you really felt in love?


This is a totally different question that the first, as when we say we’re in love can be a whole seperate thing that actually feeling it. And you’d be surprised what weird situations can prompt someone to say those words.

3. Describe your faith (or lack of it).

Hearing someone talk about their religion, or lack thereof, can be a really enlightening thing for a relationship- after all, everyone has their own personal outlook on religion and faith, and putting it into words can help clarify it for both of you.

4. Do you want to raise children in your faith?

This is an important question to get out there, as, if you’re planning on having kids, establishing whether they’ll be raised into your religion or allowed to make their own mind up is vitally important.

5. Could you ever forgive cheating?


No, you’re not just looking for a get-out-jail-free-card here- questioning him about his reaction to cheating can be an interesting way to discover his opinion on infidelity in general.

6. How do you feel about your exes?

You’re not just trying to start a fight here, as the way guys talk about their exes- if it’s angry and bitter, or just fond memories- can enlighten you on his attitudes to relationships in general.

7. What book changed your life, and how?

Literature can have a profound affect on it’s readers-find out what character, story, or author changed the way he looked at life.


8. What do you think of one-night stands?

His attitude to casual sex is a good way to gauge his attitude to sexuality in general- he might be more free and easy, or just more interested in monogamy.

9. What’s one question you would never answer?

Obviously, you don’t have to push him for the answer afterwards, but knowing the areas he’s not comfortable talking about is handy.

10. Where do you see yourself in five/ten years?


This is a good way to work out if your life goals are on a similar trajectory- does he want kids and a career, or to be off travelling the world.

11. What’s your biggest insecurity?

However confident he may seem, finding out his insecurities can let you know what you need to work on to make sure he feels great about himself.

12. What’s the best moment of your life so far?

best moments

Finding out what he cherishes as the finest moment of their life to date can be a great way to bond, and a way to help build plans for the future.

13. What’s your biggest pet phobia?


Everyone has something that they are just a little bit deathly afraid of- find out his and work out how you can pick a REALLY scary movie next time.

14. Do you consider yourself good with money?

Basically, does he think that he’s got good financial sense? If he does, fantastic, if he doesn’t, good on him for the honest, and at least you can plan for the future.

15. Do you consider your friends or family more important?


This is an interesting one, as finding out precisely where his pals and his kin come in his list of priorities can give you an idea of where you stand without having to straight out come out and ask him. Although you can do that to if you’re feeling brave.

16. What are you most ashamed of?

ashamed of

Is it some naughty thing as he did as a child, or is it some moral code he broke as an adult? Work out the thing he’s too scared to tell almost anything else.

17. Would you move for a dream job?


The chances of an amazing job offer coming up somewhere that he doesn’t already live are not minuscule, so working out what he’d do in that scenario is a pretty important factor to consider.

18. What do you think of open relationships/polyamory?

Yeah, most people think that a guy’s ultimate fantasy is to date a bunch of women, but there’s a chance that he’d never consider it. This is a fun question, that you might find opening doors…

19. What do you think the perfect work/life balance is?


As most people will put one above the other, sometimes without even realising it, finding out where your man puts his personal life versus his career is an interesting one.

20. What’s the most exciting thing about your future?

Reasons to Get Married

Is it getting married, having kids, advancing his career? This is another good way to work out his priorities and how they fit in with yours.

21. What’s your stance on lying?

While there’s sometimes room for a little white lie, discovering how far he considers lying to be an unforgivable thing will allow you a valuable look into his psyche.

22. Would you ever consider getting a joint bank account?

joint bank account

A good way to check out how much he trusts you with both your money, and whether he wants to be in control of his cash and not anyone elses.

23. If you one wish, what would you do with it?


Taking away the traditional three wishes wishes will make him get his priorities straight- what’s the one thing he would really want?

24. How important is sex in a relationship for you?

passion lovers

Although you’ll probably have an idea about this already, it’s worth establishing exactly how important these things are to your partner.

25. How many children do you want?


Depending on the stage of your relationship this is either a fun question, or an actual consideration you’ll have to take into account.

26. What kind of education do you want your children to have?

Is he desperate for any potential sprogs to head off to university, or does he want to leave it up to them?

27. What’s your perfect idea of romance?


Whether he’s more about sitting in with awesome movies or taking you out for endless dinners by candlelight, what constitutes romance to him?

28. What would you like to change about yourself?

Everything has one thing that they’re not happy with- what one thing, personal or physical, would he switch out for a better model?

29. What’s the one thing you wouldn’t want your family to know?

deep secret

It might be a little, private thing, or it might be something that he’s mentioned to you. Make sure to take note of this and not blurt it in front of the in-laws?

30. What do you think is the perfect age for marriage?


Find out when he thinks would be the right time to head up the aisle, but try not to pressure him for an imminent time frame.

31. Describe your perfect girlfriend (without talking about the physical side).


Get him to lay out how he’d want his perfect lady to treat him- try not to get to down on yourself, and remember that you’re together for a reason!

32. What habit would you like to break?

Does he smoke, bite his nails, or just leave the rubbish out? Whatever it is, you can work together to make him happier within himself.

33. What do you think of abortion?


This is an important topic for all couples to discuss if they don’t intend to have children, even though it might seem awkward at first.

34. Does your job make you happy?


Sometimes, we need a nudge to say the things we’re nervous about saying- working out whether or not he’s genuinely happy is his career can be a good way to push him to find a job that DOES make him happy.

35. If you could change the whole world in one way, what would it be?

wishFind out what thing bothers him about the world, and how he would make one significant change- whether it be world peace, or a cure for cancer.

36. If you could change one thing about your past, what would it be?


It might be an embarrassing thing he did in high school, or it might be something he did to hurt someone else- but what would he change if he had a time machine?

37. How important is physical attractiveness in a relationship?

body language

If you guys are planning to grow old together, finding out how he’s going to deal with the fact that you’ll both change when you get older is important.

38. What one experience has defined you as a person?

Everyone has one, pivotal moment in their life that they feel has influenced how they are as a person- what was hit?

39. Do you hold grudges?

let things go

Is the type who will mull over some percieved slight for days, or is he happy to just shrug and let everything go?

40. What do you think of being together forever?

grow together

Is he more of a cynic, or an old romantic at heart? Find out where your man stands on the whole lifelong romance thing.


Leave a Reply

Your email address will not be published. Required fields are marked *