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70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

Have you ever thought about trick questions to ask your boyfriend? You know, the type of questions that make him think before he speaks, even though there are no right or wrong answers? I have, and I’m here to share some of them with you.

If you’re anything like me, you enjoy listening to your boyfriend’s thoughts while he’s answering these and keeping the conversation going. Also, if you’re on a first date with him, or you just started dating, you can ask some of these questions to check if he’s boyfriend material.

Talking about different things, including some hypothetical questions, will strengthen your relationship and spice up everyday dialogue. So, don’t shy away from it. Ask questions often and learn about your partner as much as you can.

Don’t think that you’ll fall out of love with him, because that’s not going to happen. It will only help you to see his point of view, especially on important matters. If you want to build a life with him, you have to know whether he’s going to up and leave when things get tough, or fight for your love.

In this list, you’ll find funny and serious questions, with short explanations of why exactly you should ask them. And I’m sure you’ll have fun in the process! Just be ready to give your answer as well, since he may request it.

So, are you ready for some great trick questions to ask your boyfriend? Let’s dive in!

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70 trick questions to ask your boyfriend

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

If you’re in a long-term relationship, you’ve probably already asked your boyfriend some of these trick questions. Now you can check what his answer truly meant. And if you only recently began dating or started a serious relationship, these are perfect ways to get to know him better.

Just don’t make it seem like interrogation when you decide to question him, because that’s not going to work out. Make it casual and don’t put pressure on him to answer. It’s okay if he can’t give you a response right now, you’ll eventually get it.

Set up the scene where he’ll feel comfortable. Go for a picnic, or ask him nonchalantly while watching a movie or doing some activity you both enjoy. Just make sure you’re not forceful, otherwise, you may end up pushing him away.

1. What made you who you are?

Not only will you learn more about him, but I guarantee you’ll fall in love a little bit more after he shares his story. He’ll probably talk about all the ups and downs that led him all the way to you. Pay attention to his body language, because it may reveal so much more than he’s willing to say.

2. What is your aspiration in life?

You know how John Lennon said that he wants nothing but to be happy? Asking your man what his aspiration is will help you get a clearer picture of his goals and dreams. You’ll be able to support his achievements and celebrate all of them with him.

3. What are you insecure about?

It’s difficult for all of us to talk about our insecurities, so asking this trick question to your boyfriend isn’t going to be as easy as it seems. He may get a bit defensive, but if he decides to be vulnerable in front of you, you’ll know how much he trusts you and that he feels comfortable in your company.

4. Do you hold grudges?

His answer will reveal a lot about his personality. He’s going to, indirectly, tell you if he’s going to bottle up negative feelings and how he handles them. Later in the relationship, he may remind you of problems from the past, so if you truly care about him, try to understand where this is coming from.

5. What are you most grateful for?

When he gives you an answer to this question, you’ll know whether or not he appreciates the small things in life and what makes him happy. It may be his family, friends, job and career, or his dog. He may also say he’s most grateful for you and make your heart melt.

6. Are you a globetrotter?

This question won’t uncover his deepest secrets, but it’ll sure help you to get to know him better. If you both share a love for world travel, you could go on adventures together, enjoying interesting cuisines and discovering new cultures.

7. What do you consider your biggest strength and weakness?

I know this sounds like a classical job interview question, but it is actually a great way to learn more about your boyfriend. If he can identify them, it means he’s self-aware – and that’s the type of person you want to be with. But if he does nothing to turn his weakness into strength, you’ve may have problems down the road.

8. Do you care more about the past, present, or future?

This will give you an insight into what he’s focused on. If he cares more about the past, he may constantly accuse you of your past mistakes and call you on them. Focusing on the future may lead to losing touch with reality, so the best answer would be present (as I said earlier, though, there are no right or wrong answers).

9. Would you like to be famous? (In what way?)

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

Knowing if he’d like to be famous and in what way will reveal his dreams to you. Not only will you get to know him better, but you’ll get a chance to urge him to pursue the career he always wanted. You may also discover whether or not he’s materialistic.

10. What are your priorities in life?

Being able to list his priorities means that he’s given them some thought before. You’ll find out if family comes first or if he’s more of a career-oriented person. Maybe dating is not on his list right now and if he clearly states this, it’s probably best to walk away.

11. What are your short-term/long-term goals?

Although the answers to these questions will be different, both of them will show you if he’s mature enough and ready to build a healthy relationship. His goals may align with yours (that would be perfect), but for a relationship to work out, they don’t necessarily have to, at least not completely.

12. Do you rehearse what you’re going to say before making a call?

This isn’t a serious trick question to ask your boyfriend but it’s actually a good one to get to know him a bit better. If he does rehearse, he may be an introvert or have anxiety. On the other hand, not rehearsing could indicate that he’s confident and quick-witted.

13. Can you tell me something I don’t know about you?

This question is simply going to bring you closer to each other. There’s always something you don’t know about your partner, no matter how much time you’ve spent together. Asking him to share an unknown fact about him will help you to determine in which direction your relationship is heading.

14. If you could go back in the past, what would you say to your younger self?

This kind of trick question will give you insight into what your boyfriend thinks he’d change if he had the power. You may learn about his biggest regret, which will only show you how much your partner trusts you.

15. If time travel is possible, what would you say to your future self?

Who wouldn’t like time traveling? Would you do it if given the chance? He may be a bit goofy and say something like “You’ll meet the most beautiful girl when you least expect it, so be patient.” Don’t blame him, he’s trying to be romantic and show his appreciation for you.

16. Do you have a role model and who is it?

As soon as he answers this one, you’ll know if he admires his dad, uncle, or some ridiculously rich celebrity. A follow-up may be to give you reasons why exactly that person. You’ll get to know his priorities and values better, and his goals will make more sense to you.

17. If you could get three wishes granted, what would they be?

This is another important question for your boyfriend if you want to know what he wants badly. His desires will come to the surface and you’ll get more topics to discuss. He may say something silly, just to make you laugh, so please appreciate that and don’t roll your eyes (unless you do it playfully too).

18. Do you think it’s important to have friends of the opposite gender while we’re in a relationship?

Sometimes he can gain a better perspective of your whole relationship if he asks his female friends for advice. The same goes for you with your male friends, but you should set some healthy boundaries for all of them since you don’t want them to interfere with your relationship.

19. What is love for you?

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

After asking your boyfriend this trick question, you’ll find out whether love is a feeling or a decision. Loving someone may be hard at times, but a peson always needs to choose their partner, no matter what. Take this opportunity to also share your understanding of love, and I hope his explanation will be the same.

20. What is the most important in a romantic relationship from your point of view?

There can be a lot of answers to this one, but you should seek at least some of the five most important aspects of romantic relationships: respect, friendship, honesty, loyalty, and trust. He may say one of them or make some combination, but make sure that both of your top-ranked ones match.

21. How do you know that you’re in love and it’s not just lust?

When he knows the difference between these two, it means that your boyfriend knows what he wants in this relationship and this trick question won’t catch him off guard. He’ll give you a clear explanation of the differences between these two and probably also tell you how he feels about you.

22. Should I believe your actions or your words?

You need to pose this trick question to your boyfriend if you notice that these two don’t match. Perhaps he keeps telling you that he loves you and cares for you, but his actions don’t support his words. You have to get to the bottom of it.

23. Do you believe in the institution of marriage?

When you ask your boyfriend this trick question, you’ll get an insight into his priorities without asking directly about them. He may even open up and talk about his parent’s marriage, or tell you the reasons that inform his opinion.

24. What is your relationship with your parents like?

His answer will help you understand where he comes from and how important his family is to him. If he grew up in a healthy environment, he’ll most probably strive to create the same for his future family. If he didn’t, you’ll know that you have to react if you notice any red flags.

25. Do you think conflicts are bad for relationships? (And do you avoid them?)

With every healthy relationship, conflicts are inevitable. They’re bound to happen, one way or another, and you both have to be ready to play fair. If he’s going to shy away whenever you disagree and he has no intention of changing that, he’s not the kind of man you want in your life.

26. Can you name some things that you’d like to have in common with your spouse?

When he answers, you’ll know whether you fit into that picture or not. Shared personality traits, hobbies, and interests are truly important for maintaining a strong and healthy relationship. If you can identify with everything he says, you’re a match made in heaven!

27. What does your perfect girlfriend/wife look like?

If he says anything else but “You,” leave him (just kidding). His answer here will give you an insight into his expectations and you’ll be able to assess if you fit the criteria or not. If he has unreasonably high standards, better leave. There will be another man out there who’ll give you that three-letter, one-word answer.

28. What would your perfect date look like?

Even though we’re used to being the ones to be spoiled, who says it can’t be vice versa as well? Show him that you care about him and surprise him with an ideal date. You’d love it if he had to do the same for you, right? So go ahead, and strengthen your bond even more.

29. Are other people important in your life, or do you think just the two of us is enough?

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

No matter how romantic it would be if he says that only your union is enough, that’s not really healthy. Yes, your relationship should be a top priority, but you also need other people in your life. Your family and close friends have always been there for you; why is it any different now?

30. Do you talk with your family about me? How often?

It’s a really good thing if he talks with them about you. This only shows how important you are in his life and how much he appreciates what you two share. However, if your boyfriend gives a negative answer to this trick question, step up your game and get that relationship on the right track, or walk away.

31. Have you ever been in love?

This would be a good thing to know, right? You don’t want to end up with a womanizer or someone immature who thinks that he’s been in love every time he dated someone. A word of caution, though: Restrain from retroactive jealousy because that has nothing to do with how he feels now.

32. What do you like the most about me?

You could get some compliments about your physical appearance when you ask your boyfriend this question, or he may praise your personality. Whatever his answer is, you’ll be able to figure out if he appreciates inner beauty or looks more.

33. What do you feel about me?

He may tell you that you’re everything he’s asked for and how he misses you the second you leave. If you’re the one he feels like he could share his dreams, hopes, and future with, he won’t hesitate to tell you that. You can expect “I love you” here as well, if you’re at that stage of the relationship.

34. Do you ever think how different our lives would be if we hadn’t met?

This question won’t give you any detailed information about him or his personality, but it will help you to know him a bit better. Did his plans for the future change? Did he give up his dream to move to another city or country because he fell in love with you? You can learn this and so much more.

35. What would you do if someone better than me enters your life?

Asking him this question will help you realize how much he respects and appreciates you. If he’d tell you that his outlook has changed, that’s nice. He can be a bit playful while answering this one, but don’t mind him. He’s probably never thought about another girl since he met you.

36. Would you go out with your friends even if I asked you not to?

You have to know that you shouldn’t control who he hangs out with, but if you notice their bad influence, it’s normal to ask him not to go. Why is this a trick question to your boyfriend? If he says he’d go regardless of your concern, you have to understand that they are a priority and move on.

37. Are you being honest with me?

You can ask him this question if you had a little disagreement or if he came home later last night and gave you a strange excuse. Checking up on his emotions and asking him if he’s being honest with you will stop you from overthinking (in case you’re struggling with that).

38. Do you think we’re moving fast?

This question is really important to ask your boyfriend, especially if you started dating recently. Sometimes men withdraw when they feel that the relationship is moving faster than they expected. If that’s why your lover has become a bit distant lately, it’s better to know the answer, right?

39. What do you expect from me?

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

Nobody’s perfect, so if he expects perfection, it’s better to walk away sooner rather than later. You don’t need someone who’ll try to fit you in a box when you’re clearly someone who stands out. Besides, we all make mistakes, so it’s impossible to be perfect all the time.

40. Can you imagine a world without me?

This one actually leaves some place for him to be a bit more romantic. He may opt for the cliche close-your-eyes-to-see-what-it-would-look-like line, or be straightforward and tell you that his world without you in it would be meaningless. If he says yes, and elaborates on that, don’t think twice – just leave.

41. How can I love you better?

Asking him how you can love him better will make him realize how deeply you care about him. He may tell you that you’re already doing a great job, which is amazing. But, don’t be offended if he gives you some tips. There are many love languages and we need to learn how to love our partners if theirs and ours differ.

42. How can I be a better partner for you?

This trick question will reveal how your boyfriend feels about your relationship and whether he wants to work on it or not. It’s important to have open communication with him so that when problems arise, you won’t spend too much time trying to solve them.

43. Do you love me as much as I love you?

This trick question for your boyfriend is a simple tease. Of course, he loves you, but it’s always nice to hear it. This may end up in an “I love you more” argument, which is absolutely adorable. Let him win from time to time because we all know you love him more.

44. Is there anything in your past that may be a threat to our relationship?

There are certain things you don’t want to know, but the past isn’t going to determine whether you’ll fall in love with him or not. Asking this trick question will help you uncover your boyfriend’s darkest secrets. The sooner you know, the better. Nothing from his past can be fatal for your union if you know it on time.

45. Has our relationship become an obligation for you?

Priorities change as soon as you start a romantic relationship with someone, so checking if he thinks about dating as an obligation is not a bad thing. Especially if you feel like he’s not as eager to go out with you as he was before. Clearing this up will help you to be there for him if he’s going through a rough patch.

46. Do you respect my opinion and wishes?

If his answer is yes, then you can expect to build a healthy relationship with your boyfriend. However, if he answers the opposite, or says that he’d do whatever he wants, you should think twice about being in a relationship with him. He doesn’t have to always put your needs before his, but it’s nice if he’s willing to do so.

47. Why don’t we spend as much time together as we used to?

If he’s spending a lot of time recently with his friends and you kind of feel like he’s not putting the same amount of effort into the relationship as when you started dating, you should ask your boyfriend this trick question. It’s normal that his priorities change with time, but you should always be number one.

48. Is everything okay between us?

You never know what’s on his mind, especially if he’s become distant for no obvious reason. Asking him this question will clarify the situation. You may need to talk about the problems, if there are any, or just need to hug and hold him close until the storm passes.

49. Would you still think I’m attractive even if I gain/lose weight?

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

This is definitely a trick question to ask your boyfriend and it may even start a fight if you don’t get the answer you expected. He may play on the safe side and say that you’ll always be attractive to him without explaining it further, but I’m sure you’ll sense if he’s being sincere or not.

50. Can I use your phone?

This is a great trick question for your boyfriend if he’s texting another girl. So if you’ve noticed he’s being odd lately, this is the easiest way to check what’s happening. On the contrary, agreeing with this proposition only proves that he’s got nothing to hide and that he trusts you completely.

51. Have you ever lied to me? Why?

This trick question will help you to get to know your boyfriend better, to see if he’s a trustworthy person. He may have told you a white lie, or he said something completely false, but whichever it is, you have to know it. I’m sure you don’t want to be in a relationship where you question every word he tells you.

52. What’s your toxic trait?

An answer to this question will help you understand if he’s aware of his toxic traits. You’ll be able to decide if that’s a red flag for you or not. Also, you may figure out if he’s willing to work on it or not. If the latter is true and you’re bothered with that characteristic, you know what to do.

53. What is worse in your opinion – an emotional or physical affair?

This is going to help you realize what he actually thinks about cheating in general. You can also check what he considers an emotional affair and what are his boundaries. Also, you’ll conclude if he may have a fling “because it’s not a big deal,” or he won’t lay eyes on another girl while being committed to you.

54. Have you ever cheated?

Clarify that you’re not asking if he cheated on a school test if he starts fooling around. It’s normal that you want to know what his previous relationships looked like. This doesn’t automatically mean that you should walk away because the phrase “cheater repeater” is not true every time. But, pay attention.

55. Would you forgive me if I cheated?

This one isn’t an easy question to answer, so give him some time. He may ask for more details about it, and depending on what he considers cheating, he’ll give you an answer. However, don’t push the limits or cross the boundaries if you want to have a successful relationship with him.

56. What do you consider cheating?

This question is vitally important. You have to know what he considers cheating and what not. Maybe flirting is a no-go for you and he thinks it’s completely harmless. He may think that going out with your guy friends is destructive to your relationship, yet you see nothing bad about it. So, you have to clear it up.

57. Do you regret being in a relationship with me?

Asking him this leaves no place for doubts or overthinking. You’ll have a clear view of your future with him. However, if he points out some things that bother him and he says that he’d like for them to be different, try changing them. But remember, your opinion counts too.

58. Have you thought about our future together?

As soon as he answers this question, you’ll know if you’re on the same wavelength. If he starts talking about how he imagines his future but leaves you out of it, you know what you have to do. However, if his future plans include you, it’s clear that you fit into his life picture.

59. What do your friends say about me?

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

If you want to win your man’s heart, it’s good if you can fit into his social circle. Since he spends a lot of time with his friends, they’ve undoubtedly already shared their first impression of you. If he’s proud to share their thoughts, you’ve definitely passed the test. If not, he’ll become awkward and try to avoid answering.

60. What do you think of my friends? Do you like them?

As important as it is that you get along with his friends, he has to like yours as well. When you ask for his opinion of your friendship circle, I hope you get a good answer. That way you won’t have problems throwing parties together or celebrating some important life events with people you deeply care about.

61. Would it bother you if I hang out with my ex?

Some boundaries have to be set when you start dating, so asking this question is completely normal. Maybe you’re good friends with your ex-boyfriend, but if your partner sees that as a bad thing, or thinks of him as a threat, there’s no reason to keep hanging out with your ex. Show respect to your partner, he deserves it.

62. Is there something you don’t like about me?

Let’s be honest, we all have at least one annoying trait and yours may drive him crazy, but he chooses not to talk about it. When you ask your boyfriend this trick question, you give him space to open up and be honest with you. He’ll appreciate it and your bond will undoubtedly grow stronger for it.

63. What are my strengths in this relationship?

Brace yourself, you’re about to be showered with compliments! He’s the one who’s been dating you this whole time, so there’s no better person to pinpoint your assets. If he knows your weaknesses, he definitely knows your strengths as well, because they’re the reason he chooses to stay.

64. If things get bad between us, what would be your reaction? Would you fight for what we have, or would you leave?

It’s truly important to know his answer to this trick question because if your boyfriend would rather flee than try harder and win you over again, there’s no point in continuing this relationship. You want someone who’s going to fight for you and not vanish when you need him the most.

65. Would you tell me the truth even though you know it may hurt me?

Honesty is one of the pillars of a healthy relationship. If he says he’d tell you the truth no matter what, that means he also trusts you blindly and has enormous respect for you. All of this points toward a bright future with him.

66. If someone flirts with me in your presence, what would your reaction be?

This is going to help you determine if he’ll make jealous scenes, throw temper tantrums, or be chilled about it. I’m not saying that he shouldn’t react at all, rather that he should make it clear you’re his girl without using his fists or bad words.

67. If a girl makes a move on you when I’m not around, how would you react and would you tell me?

I guess this is a real trick question that reveals a lot about your boyfriend. Depending on how he’d react, you may conclude if he’s prone to cheating or not. Some of them will use the opportunity if they get it. Also, deciding to tell you proves how much he trusts you and how honest he is with you.

68. Would you still love me the same if I break down in front of you?

He has to love all of your pieces, no ifs, and buts. If you let yourself be vulnerable in front of him, he should realize that he’s your safe place and that you didn’t break down for no reason. That’s when your boyfriend needs to hold you tight.

69. If you could change one thing about our relationship, what would it be?

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)

Your boyfriend may be a bit confused by this trick question, especially if he never thought that your relationship lacks something. But, if he gives you an answer, it’s a great opportunity to then talk about it and find a middle ground.

70. Who do you talk to when we fight?

This trick question helps you understand who your boyfriend confides in when he has an argument with you. Maybe it’s his mom, his cousin, or his best friend. It’s good to know who has his back in those times.

Avoid this question completely: Do I look fat in this outfit?

This is the question guys are taught to avoid answering. Don’t act like there is any right answer here. You’ll yell at him if he says that you do look fat, and even if he says that you don’t look fat in that particular outfit, you’ll get mad because what, in something else, you do look fat?!

There are plenty of trick questions you can ask your boyfriend to answer, just make sure you don’t pose those that may kickstart a heated fight. It’s all about having fun getting to know each other better!

70 Trick Questions To Ask Your Boyfriend (Get To Know Him Better)