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40 Personal Questions To Ask Your Boyfriend

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A healthy relationship needs to be based on good communication. Most people have heard this, but it’s one of those things that’s easier said than done. We aren’t all great at coming up with questions to keep conversations going. It can also be difficult to overcome the nervousness that can exist during the early stages of a relationship.

Still, no matter how hard it might be for you to ask questions it’s important that you push through and get some answers. Some questions will help you determine if your relationship will last while others will strengthen your bond by showing your boyfriend that you are interested in him. To get you started on the right track we’ve prepared a list of 40 personal questions you can ask your boyfriend to improve your relationship.

1. What first attracted you to me?

You want to know what your man sees in you. See if you can find out what attracted him to you physically and emotionally, since both of these dimensions are crucial for a truly healthy relationship.

2. When did you realize you were in love with me?

Be careful asking this question; you should only ask it after he has told you he loves you. Also, be prepared for him to send the question right back your way.

3. What is the most important thing in your life?

Feel free to add, “besides me” if you don’t want to pressure him into saying you’re the most important thing to him. However you phrase the question, the goal is to get an idea of what his priorities are.

4. Where do you see yourself in the future?

Some guys think a lot about the future while others live in the moment. You can be more specific with this question, asking where he wants to be in one year, five years, or 10 years. This question will help you see if he’s ambitious or aimless.

5. What is your relationship with your family like?

You can tell a lot about a person from their relationship with their family. Just remember that everyone has a different relationship with their relatives.



If you have a healthy, close relationship with your family, it can take some time to understand a person who was raised by distant or abusive parents. Be slow to judge and take the time to understand where they are coming from.

6. Do you prefer going out or staying home?

They say there are two types of people, those who nest at home and those who are always out on the town. As life goes on people, tend to gravitate towards a homier life, but if your relationship starts out mismatched, then you might have some troubles.

7. Do you want to have kids?

This is a big one. If you want kids and he doesn’t, or vice versa, then sooner or later there are going to be issues. People can change over time, but it’s dangerous to build a relationship on hopes that your partner’s life philosophy will change dramatically.

8. How many kids do you want to have?

Following up on the last question you will be looking to see if your ideas about the ideal family match. Try and see if compromise is possible or if your philosophies are irreconcilable.

9. When do you think you’d be ready to have children?

Pay attention to see if they want to have children sooner or later. If they’re in a hurry to have kids and you aren’t ready then, or vice versa, then trouble might be just around the corner.

10. What are you most proud of?

You might be surprised by what he considers to be his best trait or biggest accomplishment.

11. What was the happiest moment of your life?

It’s always good to bring up positive memories. The more you learn about his life the closer you will grow together, and positive experiences are a lot more fun to talk about than their negative counterparts.

12. What is the first thing you can remember?

Another question about his past. Get close to him by taking a trip back to the earliest days he can recall.



13. Do you have a hero or idol?

When you know who a person’s heroes are you can get a sense of the type of person they want to be.

14. Who has disappointed you the most?

We’ve all been let down by people we trusted. This question can show you what his values are and where he draws moral lines.

15. If you could change one thing about yourself, what would it be?

Everyone has insecurities. By finding out your boyfriend’s, you can help encourage him to either make the changes he wants to make or accept things about himself that he struggles with.

16. What are you most afraid of?

Don’t make fun of him if you don’t understand his fear; you need to be as supportive as you can be as long as he answers this question honestly.

17. Are you good with finances?

Financial problems are the number one cause of death. No matter how much you love, someone money trouble can still push you away from them. Try and find out early if your boyfriend has money problems so you can decide if they can be overcome or not.

18. Do you save money or spend it as soon as you get it?

Spenders who marry savers are getting a good deal and savers who marry savers are setting themselves up for a comfortable future. When spenders marry spenders, drama is on the way, be careful.

19. How do you deal with stress?

Do they bottle things up or let them out? You want to help him deal with stress in healthy ways; you don’t want a boy who takes his stress out on you.

20. Is there anything you consider unforgivable?

Don’t ask this question to see what you can get away with it, ask it to get a sense of their moral philosophy.

21. What do you think the meaning of life is?

This isn’t an easy question to answer. In fact, some people think it’s impossible to answer. But it’s always worth thinking about, and finding out what your boyfriend thinks will help you understand him better.

22. How important is sex for you?

Contrary to popular opinion there are guys who aren’t particularly interested in sex. There are also plenty of guys who like sex but have higher priorities. Try and find what your man says about the subject, while seeing if his actions match his words.

23. How often do you want to have sex?

Once again, not every guy wants to have sex every day. You want to see what his ideals are, and figure out if you can live with them.

24. What is your favorite thing to do in the bedroom?

Romance isn’t just about quantity; it’s also about quality. Even if you can’t make much time for love-making, you can still make the most out of every session, as long as you have compatible interests. If you’re not willing to provide him with the things he’s craving for then you might have issues later on.

25. What is your favorite meal?

They say the quickest way to a man’s heart is through his stomach. If you can cook your man’s favorite meal, or arrange for a date at a restaurant that serves it, then he will be very thankful.

26. Why did your past relationships end?

Was he dumped or did he do the dumping? Are him and his ex still friendly or is there still bad blood? It’s hard to think about your man being with another woman but chances are you aren’t the first woman in his life, learning about his last relationship will give you some idea about your current relationship.

27. How do you feel about divorce?

This is a question with no easy answers. It’s nice to hear that a man believes in love that lasts forever but this can also lead to men who will accept unhappiness and allow a loveless relationship to just drift along.

28. What does love mean to you?

It can be hard to know what a man means when he says he loves you if you’ve never asked him this question. We all use the word love, but it means something different to each of us.

29. What does commitment mean to you?

Every relationship has boundaries, whether they are explicit or not. It’s important to talk about them so you know what’s expected of you, and what you should expect from him.

30. What makes you feel jealous?

Jealousy is a completely natural human emotion. Every person deals with it differently. The important thing is finding a healthy way to handle it. Find out what makes your man jealous and see how you can help him deal with this potentially dangerous feeling.

31. What does he consider cheating?

This question might be implied by some of the previous questions, but it’s worth making it explicit. Almost everyone agrees that having sex with someone else is cheating, but the potential dangers of “emotional cheating” shouldn’t be quickly dismissed.

32. If we got married how do you want to handle last names?

This is one of those technical matters that many people put off too long. Is your man old fashioned or is he interested in a more “modern” way of handling the issue? It’s worth figuring out.

33. What are your favorite and least favorite household chores?

If you move in with your boyfriend, you will have to figure out a way to divide chores, and this question will give you some idea of how that division might work out. Hopefully, you don’t mind the chores he hates, and he’s willing to do the chores you can’t stand.

34. Do you have any allergies?

This will help you keep your man healthy. It’s also worth knowing if he’s allergic to cats or dogs if you have your heart set on getting a pet at some point.

35. What do you think is the biggest problem with the world today?

Everyone wants to change something about the world, and all of us can make a difference, even if it’s just a small one. Find out what sorts of priorities your boyfriend has.

36. Do you believe in soul mates?

See if he’s more of a romantic or a realist. If your personal philosophies clash, then you should find out as early as possible so you can avoid unnecessary pain and confusion.

37. Are you happy alone or do you need to be with someone?

Human beings are social creatures by nature, but some are more social than others. This question will help you find out why your boyfriend might come off as clingy or distant.

38. Who is your best friend?

You’re not the only person in your man’s life, and that’s OK. Everyone should have friends, find out who your boyfriend’s best friend is and encourage them to spend time together.

39. What keeps you up at night?

We all have worries; it’s good to know what worries your boyfriend. You might not be able to solve his problems for him, but you can be there for him and provide emotional support.

40. What makes you feel appreciated?

Everyone needs to feel appreciated. It’s even more important to a healthy relationship than sex. But different things make different people feel appreciated. Your boyfriend may not react to the same gestures that resonate with you. Find out what makes him feel appreciated and try and provide him with what he needs.

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