50 Trick Questions To Ask Your Boyfriend

You know, there is something very VERY important I have learned over the years. It’s this – the more you get to know someone, the more difficult it becomes to love them. 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 more.

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. Or you can use some of these trick questions to ask your boyfriend to see if he’s cheating on you. These questions will even save you from delaying an inevitable breakup.

But before that, let’s also look at the questions you should NOT ask your boyfriend. Don’t confuse funny trick questions to ask your boyfriend with “let’s make him awkward by putting him in a spot”. No, girl, please don’t dig your own grave.

Trick Questions You Should Avoid Asking Your Boyfriend

• “Who would you choose, me or your friends?”
• “Was your ex better than me in bed?”
• “Do I look fat in this dress?”
• “Do you remember the exact date of our first kiss?”
• “When are we getting married?”
• “What would you name our future kids?”
• “If you had an option to date one of my friends, who would it be?”
• “If I died, how long would it take you to move on?”
• “Hypothetically, which one of your friends would you kiss?”
• “Do you even think of breaking up with me?”

50 Trick Questions To Ask Your Boyfriend

Men are from Mars and women are from Venus, right? Each gender has its own set of emotional balances and ways of communicating. Men think and behave differently from women, which can make it difficult to get 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, and these questions will facilitate just that. 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 who are lucky, get a chance to experience their first dates on beaches. What is your boyfriend’s MO on a first date? Ask and find out.

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 others 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?

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, if he believes in zodiac sign characteristics, and his take on 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. Our first memory (in fact, a cluster of our earliest memories) contributes a lot to our mental health, and that’s why this is an important question to ask you SO.

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?

Try to get your boyfriend to open up about his childhood friends or mischievous things 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?

I ask this to everyone 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.

10. Did you have any pets growing up?

Having a pet teaches responsibility and instills a sense of empathy in kids and adults. So, 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?

This is one of the vital trick questions to ask your boyfriend to get to know him more. Some people like to spend time with their families on their birthday. Some like to go out and drink till they drop. What does your boyfriend prefer? You gotta know so that you can plan the perfect day for him on his next birthday.

Related Reading: Top 16 Symbols Of Love With Their Meanings

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

This is one of the questions to trick your boyfriend because it will help you dive deeper into his personality. His relationship with his parents has a lot to do with why he is the way he is.

13. What’s on your bucket list?

This is one of those cute trick questions to ask your boyfriend to find out the things he may be looking forward to doing with you. Share your bucket list with him. Or maybe create an ultimate couple bucket list. That will help strengthen your 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? Where would he like to travel with you? This will help you understand if your travel styles align.

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. Find out what his thoughts were and how young he was when he had his first kiss.

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

Guys never forget their first time. It is important you know who their first was, or at least when. Find out how they felt about losing their virginity. This will give you a lot of insight into the person he is, which can come in handy in figuring out 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 tricky 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 whatnot! Ask these trick questions to ask your boyfriend to see what his fantasies are like.

20. What are your sexual fantasies?

Speaking of fantasies, you need to know what makes him tick sexually. There is a survey that says the majority of people have dreamt of a threesome. 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.

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 about 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 unless they are in love?

Pssst, that’s me. I don’t feel sexually aroused unless I am head over heels in love with the person. 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 among the serious relationship questions to know where your partner draws a line in the sand. 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!

25. Do you have any fetishes?

All fetishes are okay as long as both partners 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 such tricky questions to ask your boyfriend could save you.

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

26. Are you artistic?

If you are artistic and lucky enough to be with a person who shares that flair, then I envy the conversations you are going to have. But if they aren’t, then you can teach him a thing or two about art.

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

This is one of the casual questions to ask your boyfriend over text. Watching movies together is so intimate. Plan a surprise movie date night! Brownie points if you order his favorite snacks as well.

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

If he says he doesn’t like dating an independent woman, then is he even the right man 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?

What if you end up cheating on him? And what if that’s a relationship deal breaker for 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?

Sex? Porn? His mobile phone? Good food? Books? Working out? These are questions to ask your boyfriend to trick him into revealing hidden sides to his personality. 

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

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 their family nor their friends 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?

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 is said healthy jealousy helps build strong relationships. But if his jealousy veers into unhealthy territory, then your relationship can get very toxic.

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

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. I haven’t yet found a guy who has said that to me.

35. Are you friends with any of your exes?

If you are okay with him still being friends with his ex, well and good. But if you are not okay with it and he is still in touch with his ex, you need to do something about it. More importantly, if he knows you’re comfortable with the friendship and chooses to pursue it anyway, you need to think about your place in his life.

36. Why didn’t your past relationships workout?

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?

Girls, when someone claims to love you, is it for your personality? If he loves you because you look like a Greek goddess, then he is a walking red flag. So, this is one of the trick questions to ask your boyfriend to see if he loves you.

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”. Whatever the answer, you must be prepared to take it on the chin.

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 hidden things. 

41. Do you see me in your future?

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 straightforward, “Would you ever cheat on me?” The direct answer to this question would be “no”. It falls on you to look at the signs of a cheating boyfriend. 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 desires 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?

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 as it ages. But boring doesn’t mean you have fallen out of love with each other. 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 partner.

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

Trust, empathy, and kindness. Always know that people aren’t perfect, but a relationship could be. Always know that relationships are hard but worth it.

49. In a day, how often or how rarely do you think of 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 about yourself 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? 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 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 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 what it will lead to in the future.

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