50 Trick Questions To Ask Your Boyfriend

trick questions to ask your boyfriend

You know, there is something very VERY important I have learnt over the years. It’s this – the more you get to know someone, the more difficult it becomes to love them. It could be due to your own personal traumas or their hidden traumas that unravel as the relationship progresses. When things get a little boring, you could have some laughs by using our list of fun trick questions to ask your boyfriend. Along with the chuckles and giggles, you can even expect to connect with him by asking such questions and getting to know him better.

Whether it is just to understand him better, or to find out if he is serious about you or not, you can choose from this list of trick questions to ask your boyfriend. Learn some trick questions to ask your boyfriend to see if he’s cheating on you. For those moments when you feel uncertain about the relationship and have doubts about his intentions, then these trick questions will save you from prolonging the breakup. These questions to ask your boyfriend to trick him will certainly make up your mind about him and the relationship.

50 Trick Questions To Ask Your Boyfriend

Table of Contents

Men are from Mars and women are from Venus, right? Each gender has their own set of emotional balances and way of communicating. Men think differently from us. Behave differently from us. Hence the difficulty in getting to know them better. This list of questions can definitely help. Starting with silly and funny questions, the list ends with complicated and deep ones. 

These funny trick questions to ask your boyfriend have been curated for you to use so that you can find out everything you need to know about him and his thoughts on relationships. From his preferences to his lifestyle to his quirks and sexual desires. The key to a good relationship is communication. We have curated a list of fun trick questions to ask your boyfriend. Go ahead, read them and ask away…

1. What do you do on your first date?

Most guys take girls out to dinner on their first date. Some analyze a date’s body language. Some take them to the beach and some who are lucky, get a chance to experience their first dates in museums and libraries. Sadly, I haven’t had a date in either of those last two places. That’s my cue to update the bucket list. And that’s your cue to get on with these trick questions to ask your boyfriend.

2. What’s the first thing you notice in a woman?

Soft hair, blue eyes, an hourglass waist, breasts, butt, or long legs? What catches your boyfriend’s eyes? Find out by asking some funny trick questions to your boyfriend and see how much appearances matter to him.

3. Do you believe in God?

Everyone has their own set of beliefs. Some believe in the oneness of God, while some believe there can be more than one God. And some absolutely disregard the existence of a supernatural deity. If religion matters to you, this question needs to be asked.

Related Reading: 55 Truth Or Dare Questions To Ask Your Boyfriend – Clean And Dirty

4. What’s your comfort food?

questions to ask your boyfriend to trick him
What’s your comfort food?

Ah, food! Most of us have a particular dish, a comfort food that we eat when we want to feel better. This question will help you out when your boyfriend is having a rough day. You can order it in or cook it for him.

5. Do you believe in Astrology and sun signs?

Some women are obsessed with sun signs and all that astrology jazz. It will be good to know what he thinks about this topic and believes in zodiac signs characteristics and whether your sun signs are compatible.

6. What’s your first ever memory?

Your first memory says a lot about you. For example, my first memory is of me crying my eyes out after I slit my palm at my 3rd birthday party. I sometimes wonder what my parents were thinking – letting me hold such a sharp knife in my hands. Our first memory helps in building our mental health.

7. What are your short term and long term goals?

Never date a person who is aimless, who has no goals in life and who isn’t passionate about anything in life. Get to know your boyfriend’s ambitions and be supportive of them just as he should be supportive of your goals and your dreams.

8. What was your childhood like?

Some have an easy life growing up while some people have had to go through trying and hard times. Try to get your boyfriend to open up on the littlest details from his childhood. Any funny story about growing up or about his childhood friends or a mischievous thing he did at school. Such cute trick questions to ask your boyfriend will deepen your understanding of him.

Related Reading: What Holding Hands Means To A Guy – 9 Interpretations

9. What was your dream profession while growing up?

This is one thing I never fail to ask anyone I meet because what we dream as kids and what we become when we grow up are very often poles apart. Look at me, I wanted to be a heart surgeon in school. Now I am a desperate writer trying to make ends meet. Dreams change as we grow up. But what matters is how determined a person is in accomplishing their dream.

10. Did you have any pets while growing up?

Having a pet teaches responsibility. Looking after them instills a sense of empathy in kids and adults. It provides companionship and reduces the feeling of loneliness. Ask such relationship building questions to your boyfriend and find out if they are a cat or dog person.

11. What do you like to do on your birthdays?

Such important yet funny questions to ask your boyfriend over text are useful because it will help you find out what they like to do, and also, who the significant people in his life are. Some people like to spend time with their families on their birthday. Some like to travel to a new place and explore new things. Some like to go out and drink till they drop. Some like to keep it lowkey and spend it at home.

Related Reading: Top 16 Symbols Of Love With Their Meanings

12. What kind of a relationship do you have with your parents and siblings?

Such important yet funny questions to ask your boyfriend over text are useful because it will help you find out what they like to do, and also, who the significant people in his life are. Some people like to spend time with their families on their birthday. Some like to travel to a new place and explore new things. Some like to go out and drink till they drop. Some like to keep it lowkey and spend it at home.

13. What’s on your bucket list?

This is one of those cute trick questions to ask your boyfriend and find out how many he is willing to do with you. Share your bucket list with him and see if there is anything you could both do together. Or maybe create an ultimate couple bucket list containing of things you both could do. That will help to strengthen the bond.

14. Which cartoon character do you find the hottest?

This is one of the funny questions to ask your boyfriend over text to keep the conversation going. Run if he says Dora, The Explorer!

15. What’s your dream destination?

Greece? Spain? The Northern Islands? What is it? Would he travel with you? If he is serious about you, then he would definitely include you in his travel plans. These are some of the light trick questions to ask your boyfriend. It is going to get a little serious now; sometimes, even hotter. Some of the questions listed below will help you to get to know what they like in bed.

16. When was your first kiss?

This is one of the questions to ask your boyfriend to trick him into opening up his bag of secrets. There are so many thoughts a girl has after her first kiss. Find out what his thoughts were and how young or how old was he when he had his first kiss and who was she? A crush or a serious girlfriend? Such trick questions to ask your boyfriend will help you discover whether you have a Casanova or a gentleman on your hands. 

17. How old were you when you lost your virginity?

You know there is a saying. Guys never forget “the first time”. It is important you know who their first was, or at least when. Was it just a one-time thing or were they in a serious relationship? Find out how they felt about losing their virginity. Such trick questions to ask your boyfriend will make you more cautious about how to proceed with the relationship.

Related Reading: Sexual Compatibility – Meaning, Importance And Signs

18. Did you fall in love with her?

Humans are weird creatures, aren’t we? Love builds us then breaks us. Builds us, then breaks us. So on and so forth, but we refuse to stop loving. Such trick questions to ask your boyfriend will help you gauge his emotional range.

19. Have you ever had the desire to date an older woman?

It’s about to get a lot more sensual. Men have weird fantasies. Dating an older woman is one of them. MILF and what not! Ask these trick questions to ask your boyfriend to see if he’s cheating on you or if he could entertain the possibility to cheat on you.

20. What are your sexual fantasies?

cute trick questions to ask your boyfriend
What are your sexual fantasies?

There is a study that says the majority of people have dreamt of a threesome. Some like power dynamics in bed. Being the one in control makes them feel strong. Rough sex, BDSM and other things. Sexual fantasies of men are plenty. Find out what’s his craziest desire Such fun trick questions to ask your boyfriend will tell you a lot about his kinky fantasies.

21. What’s your favorite position in bed?

Find this out and use it to your advantage when you get in bed with him. Learn what makes him lose control by asking him his favorite position. 

Related Reading: Expert Tells You How To Have A Good Sex Life After Being Parents

22. Where’s the strangest place you’ve had sex?

At the foot of the bed? Boring. Public restrooms? Flights? Park? Interesting. Steamy. Ask such funny questions to your boyfriend over text and make him fantasize about you. 

23. Are you one of those people who can’t have sex or can’t finish when they aren’t in love?

Pssst, that’s me. I can’t come unless I am head over heels in love. I need to be in love at that exact moment to finish. If that’s the case with you or your partner, then it’ll be clear whether or not he has genuine feelings for you.

24. Would you date an ex’s sister or their best friend?

This is a very serious relationship questions to know where you stand. Trick question to ask your boyfriend to see if he’s cheating or would ever cheat on you in the future. Dating an ex’s best friend or sibling is a big no-no! Always be wary of people who do that.

25. Do you have any fetishes?

All fetishes are okay as long as the doer and the participant are in agreement over them. If his fetishes sound crazy to you or you think it’s a red flag and you should end the relationship, then these tricky questions to ask your boyfriend will save you.

Moving on to the deeper stuff – emotional and heart-rending.

Related Reading: 100 Deep Conversation Topics: Questions About Love And Life

26. Are you artistic?

The answer is as simple as it can get. A person is either artistic or not. If you are artistic and lucky enough to be with a person who is artistic, then I envy the conversations you are going to have with them. But if they aren’t, then you can teach him a thing or two about art and that’s a cute way to share the things you love with him.

27. What kind of music and movies do you like?

This is one of the funny questions to ask your boyfriend over text. Watching movies together, in my personal experience, is one of the greatest joys to experience with a loved one. It is so intimate. Find out what movies and music he likes and indulge him. Plan a surprise movie date night! Brownie points if you order his favorite snacks as well.

funny questions to ask your boyfriend

28. What’s one thing you cannot tolerate in your girlfriend?

You need to know the answer to this before you are knee deep in love. There are some men who are so controlling that they don’t like their girlfriends to show skin. Some don’t like a strong, working woman, because they feel intimidated. Some are just too shallow to admit they are all about looks and appearances. If he doesn’t like dating an independent woman, then he’s not the right one for you. Know what your boyfriend wants, and if that’s not you then walk away – that will be his loss.

29. What’s the deal breaker for you in a relationship?

This will prepare you for the future. What if you end up cheating on him? And what if that’s a relationship deal breaker for him? What if he cannot stand lies or cannot stand you disrespecting him? Such tricky questions to ask your boyfriend will come to your aid at difficult times.

Related Reading: Relationship Advice For Couples- 25 Ways To Strengthen Your Bond

30. What is one thing you cannot live without?

What is one thing he cannot live without? Sex? Porn? His mobile phone? Good food? Books? Working out? There are so many things you can find out about a person by learning about that one thing they cannot live without. These are questions to ask your boyfriend to trick him and find out about his true intentions regarding you. 

31. What do your family and friends think about me?

This is one of the deep relationship questions to ask for a better love life. Men who are family oriented take into strong consideration their family’s advice and opinions. If your boyfriend has a best friend, or worse, a female best friend, then finding out what they think about you becomes essential. If neither of them like you, there are chances that the relationship could be at stake.

32. I know I am a lot to handle. Are you up for it?

I am sure every girl at some point in the relationship has asked herself if she is a lot to handle, and if indeed she is, then will it be too much for him? But let me tell you something, it doesn’t matter how needy or how much of an attention seeker you are, if he loves you truly then he will give you everything you ask for and more. He will be up for everything you are.

Related Reading: 28 Fun Things To Do With Your Boyfriend At Home

33. Would you be jealous if you saw me with other guys?

It’s a straightforward question to which he should answer just as straightforwardly. Yes or no. If it’s a ‘No’ or if he says anything besides ‘Yes’, then he doesn’t care about who slides his hands down your back. He doesn’t love you. It is said healthy jealousy helps build strong relationships. If a man doesn’t get jealous or envious at just the thought of you being with someone else, then he is not the right guy for you.

34. Would you miss me if we never talked again?

It’s a deep one, I know. But nevertheless one of the very important trick questions to ask your boyfriend. To get out of the tough spot, he will say he will miss you. I’ll get a little complicated here and tell you something interesting. If I happened to ask my boyfriend something like that, I would secretly hope for him to answer with something like this, “Why would I miss you when we are never going to stop talking?” The search is still on people. I haven’t yet found a guy who has said that to me.

35. Are you friends with any of your exes?

I am of the belief exes can never be friends. But to each his own. If you are okay with him still being friends with his ex then the decision is all yours. But if you are not okay with it and he is still in touch with his ex then you need to do something about it. Such tricky questions to ask your boyfriend will let you know if he is still in contact with his past lovers.

36. Why didn’t your past relationships workout?

There are two sides to every story, right? Two sides of the same coin. Who left whom? What was the reason behind the break up? Some people think the past is better left there, in the past. But why? Why can’t you know what went wrong between the man you are in love with now and the woman he was in love with before you? Don’t think you are being nosey. You are just being curious about the man you love. And once you find out everything that happened, be mindful and accept your partner’s past.

37. Would you still love me when I get old and wrinkly?

Over time, beauty fades. All that remains is wrinkles on your face and a troublesome hip. Girls, when someone claims to love you, then always make sure they love you for your personality, sense of humor and your independence. If he loves you because you look like a Greek goddess then he is into you only because of your appearance.

38. What’s one thing you want to change about me?

This is one of the trick questions to ask your boyfriend about yourself. He could answer by saying something like, “Your sleep schedule”, “Your habit of biting nails” or “You need to stop eating so much junk food”. If his answers are related to your health and he is concerned about you, then he is a sure shot keeper. 

Related Reading: Dating Vs Relationship – 8 Subtle Differences You Never Knew About

39. Have I done anything to hurt or offend you?

Just so you are careful about it in the future, these are good trick questions to ask your boyfriend about yourself. This will keep the relationship strong. You will find out what triggers him and what not to say or do to offend him.

40. Have you ever dreamt about me?

What a poetic thing to ask him! Dreams are always vague but they signify what a person thinks about you as dreams are your mind’s way of signaling you about the hidden things. 

41. Do you see me in your future plans?

We all think about our future every now and then. This is one of the important trick questions to ask your boyfriend. If he keeps talking about a future with you, then he is serious about you and wants you in all the upcoming phases of his life.

42. If you find someone hotter and better than me, would you tell me after you slept with her or would you sleep with her and never tell me about it?

There is a reason why this question isn’t as simple as the straight forward, Would you ever cheat on me?” The direct answer to this question would be ‘No’. Because why would anyone ever tell you beforehand that they have plans of cheating on you? It falls on you to look at the signs of a cheating boyfriend and analyze the situation. Such trick questions to ask your boyfriend to see if he’s cheating on you will safeguard you from a lot of pain.

43. What is your darkest desire and secret?

Secrets and desire make a person interesting. It is exciting to get to know someone on a deeper level where you can discuss deepest, darkest desires and secrets.

44. If we were to get married, what would you expect out of me and the relationship?

funny trick questions to ask your boyfriend
If we were to get married, what would you expect out of me and the relationship?

Expectations are what bring a person’s morale down. Imagine having high expectations from someone and they don’t live up to them? That’s no fun at all. Always keep your expectations low, because when they don’t live up to them, it creates problems and fights. God! So many fights.

45. Do you find me as interesting and as attractive as you did when you first met me?

Every relationship is bound to get a little boring. But boring isn’t bad. Boring is good. It’s a normal emotion. Boring doesn’t mean you have fallen out of love with someone. There is a very thin line between being bored and falling out of love. Make sure he knows the difference.

Related Reading: 33 Questions To Ask Your Significant Other To Know Them Better

46. If my parents get sick, will you help me in taking care of them?

An act of pure kindness. I always say kindness trumps every other trait in the world. To take care of someone who took care of you once is one of the greatest blessings ever.

47. Does spending time with me exhaust you or do you love it?

If he loves you, you will never be the reason for his exhaustion. Your boyfriend should want to spend a lot of quality time with you. This is one of the cute trick questions to ask your boyfriend.

48. What qualities do you think our relationship should have?

Trust, empathy, kindness and gentleness. Always know that people aren’t perfect, but a relationship could be. People can be flawed, but not a relationship. Always know that relationships are hard but worth it. Two people can fight all they want, but at the end of the day, what are they fighting for? Are they fighting to save the relationship or fighting to get out of it?

49. In a day, how often or how rarely do you think or me?

He can be very occupied and still think about you. He can be free all day and yet not think about you at all. Such trick questions to ask your boyfriend will help you assess where the relationship is headed and how to deal with it.

50. How do I make you feel?

Does he feel like he is sitting by the ocean hearing the waves crash against the shore when he is with you? Does he feel like burning down the house in your presence? Does he feel like standing in the rain soaking up the raindrops when you make tea for him? Or does he want to go for a jog to clear his head when you are home? You should know how he feels about you. Even if not in such a poetic way, then at least in plain simple terms. 

The trick isn’t in just asking these questions. The trick is in noticing where he pauses, where he stutters, where he gulps his words down without letting them escape his lips. The trick is in reading between the lines and in knowing how to bring them up in simple conversations. These cute trick questions to ask your boyfriend will help you navigate where the relationship is at present and where it will lead to in the future.

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