Find Out What’s Under His Charming Personality With These 59 Trick Questions To Ask Your Boyfriend

We promise not to tell anyone you're looking for trick questions to ask your boyfriend.

In fact, we applaud you!

Using fun, clever, and tricky questions to probe the nature, depth, and intensity of your boyfriend's feelings is smart.

You can gain a lot of insight while seeming to keep things light.

It's genius!

What Are Trick Questions, And Why Should You Ask Them? 

At first, the idea of “trick questions” may sound manipulative. And truthfully, some inquiries cross the line (which we'll explore more at the end of the article). 

But general questions to test your boyfriend are rooted in honesty; they're just worded in a way that may get him to open up more.

Way to get to know him better and vice versa

  • Have fun and keep him guessing
  • Promote conversation
  • Learn about his past
  • Figure out his personality quirks
  • Determine if he's being honest with you

59 Trick Questions to Ask Your Boyfriend 

We've discussed the benefits of asking your boyfriend trick questions. Now, let's look at possibilities. We tried to develop questions for a wide swath of people.

So every question won't be for everyone. Regardless, use what works and disregard the rest.

Tricky Questions To Ask Your Boyfriend

These questions may throw your man for a loop — but they won't make him run in the opposite direction.

1. What groups of people do you find the most attractive?

Everyone has their preferences. So if you're in the early days of dating, it's a way to determine if you're his usual type. 

2. If you could change one thing about me, what would it be?

Only ask this question if you're prepared for an honest answer. We'd recommend throwing this out when you're in a steady relationship and not before. 

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

This excellent early-dating question gives insight into how the guy feels about himself and what he values.

It's also a way to suss out his insecurities so you don't stumble upon one early in the relationship. 

4. Who was the first and last person to break your heart (so far)?

Learning about someone's history is important if things are starting to get serious. It helps build a strong bond and provides insight into his past loves.

5. How would you feel if I struck up a friendship with an ex?

Is your man the jealous type? If you want to gain insight, the answer to this question could give you clues.

But understand that some men don't love when their partners hang with old lovers if there is still a potential for the flame to reignite. 

6. Do you think we should tell each other if we're in the presence of someone we've slept with?

Hold this question until you've decided to commit to one another. If you're casually dating, there's no need to dive into this line of inquiry.

7. What should I do about my high school boyfriend who's flirting with me on social media?

This is another question to test his jealousy quotient. Extend the inquiry by asking if he's social media friends with old flames.

man holding a glass of wine talking to girl trick questions to ask your boyfriend

8. Do you ever think there will be a time when your relationships matter more than your career?

Framing the question this way lets him know you understand his current focus, which is respectful. But if he says, “never,” and that doesn't sit well with you, it may be time to reconsider the relationship.

9. Is there anyone from your past that I should know about?

Life is complicated, and many people have pasts. If you've been dating for a while, finding out if anyone may try to sabotage your relationship is a good idea.

10. Are we moving too fast?

You can ask this question if you feel like things or speeding or lagging. It will also give you a peek into where he thinks the situation is headed. 

Trick Love Questions

Want to plumb the depths of your man's thoughts to figure out how he's genuinely feeling about you and the relationship?

Try these questions.

1. How many significant others have told you they love you?

This will give you an idea about his past love history. If he's been in love a lot, he may be a serial monogamous or fall in love easily.

Keep this question under wraps until you've been dating for at least two months. 

2. Have you ever said “I love you” to someone you just wanted to sleep with?

It happens. Sometimes, people say things they don't mean in an attempt to weasel their way to intimacy. So find out if your man was a player in his past — or possibly still could be.

3. Who was the first person you loved?

Young love is so precious and intense. Find out who his first love was. If he's younger, he may not have crashed hard yet, and that's okay! 

4. What would you do if [insert his favorite famous crush] asked you out?

A twist on the classic “hall pass” question, this will get your boyfriend dreaming. Plus, it also gives a clue as to where he sees your relationship.  

5. What would make you love me more?

This question should be reserved for people who have been together for a while.

But be careful. It has to be asked at the exact right moment. Otherwise, you may come across as desperate.

6. What do you think of your parent's relationship? Is it something to which you aspire? Or is it more of a cautionary tale?

The answer will give you insight into his family situation. Plus, his response will reveal what he's currently looking for in a relationship. 

7. When do you know you're settling for someone?

Pay close attention to what he says. Then think whether he's demonstrated those traits with you.

8. How comfortable would you be if I had a long conversation with your ex?

This is a great, sneaky question that will give you lots of info. Don't just pay attention to what he says.

Make a note of his body language, too. Is he huffy? Scared? If so, he may be hiding something.

9. Would you tell me if one of your friends or family members didn't like me?

If getting along with his friends and family is important to you, bust this out during a getting-to-know-you conversation.

It will reveal how he handles conflicts and give clues about his family bonds.

10. How much longer do you intend to play games?

Drop this on the table if you're fed up and ready to get serious or move on. It's sassy, confident and will provide insight into where his head is at.

Trick Questions to Ask a Cheater

Do you suspect your man is stepping out? Is he sampling a little “strange”? Throw around the following questions to sniff around the issue.

1. What constitutes cheating, in your opinion?

Does he believe it's only physical? Does it count when he's drunk? Fair warning: Cheaters will likely have very narrow definitions. 

couple having a date trick questions to ask your boyfriend

2. Do you think there's a difference between emotional and physical infidelity?

Pay attention to his answer and make note if it meshes with yours. If not, that's a conversation you may want to have if things progress.

3. Tell me about the first time you lost your virginity.

Talking about your “first time” is perfectly acceptable when sex is on the docket. So is having a conversation about sexual health.

4. Are you afraid of breaking up with me because you think I'll react terribly?

Do you think things are rocky? Do you think he's holding on out of politeness? If yes, cut to the chase. 

5. Would you be relieved or upset if I started dating someone else?

This is another inquiry for when things are at a low ebb and you're considering whether to cut your losses and run. If he's indifferent, you have your answer.

6. How would you react if you discovered I was cheating on you?

Not only will you get a straight answer on his expectations about your behavior, but it may also provide insight into what he's doing when you're not around.

7. Is there anyone with whom you are completely honest?

A flat-out “no” is a giant red flag — especially if he's bold enough to admit it. If he answers with a name, consider probing that person if you think he's cheating.

They probably won't tell you anything, but body language can reveal a lot.

8. What would I see if I ran into your friends out partying?

Does he roll with a crazy party crew, or is his circle more low-key? The answer to this question will reveal all.

9. Have you ever had an STD? When was the last time?

Sexual health isn't a joke; you have every right to inquire if you plan to sleep with someone.


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Questions To Ask Your Boyfriend About You To See if He Knows You

Are you curious about how well your man knows you? Toss some of these questions into the conversation.

1. What is my middle name?

It may be something to raise an eyebrow over if you've been together for a while and he doesn't know. But if you've only been dating a handful of weeks, don't get in a huff.

2. It's February. Would I rather go on vacation in the Caribbean or Canada?

Does he know your vacation preferences? If so, it's a sign that he's paying attention and taking note of your tastes.

3. What was my favorite thing about my hometown? Least favorite?

Some people have a complicated connection to their hometowns. So if it's early days and he doesn't want to talk about it, let it go.

4. Do you think I'll go to my 50th high school reunion?

Are you a joiner or not? What does he think? The answer to this question will let you know.

5. How would I react if I found out something bad about you?

Does he have a handle on your temperament? Does he understand your expectations about the relationship?

Throwing this out will give you insight into both questions.

6. What would I consider a total waste of money: a home theater, an expensive car, or a gourmet kitchen?

Everyone has priorities. Does he know what you value and what you could care less about? 

7. What movie could you not make me sit through?

Discover if he knows your film preferences by asking this question.

8. What's my ultimate professional goal?

If your career goals are a top priority, figure out if he's been paying attention by asking this question.

9. Which family member do I like the best?

Does he pay close attention when you're talking about your friends and family? This inquiry will reveal the answer.

10. What do you think my friends think of you?

This is an excellent twist on an uncomfortable question. Plus, it will provide insight into how he sees himself. 

Random Trick Questions

We'll end with a few random trick questions for your boyfriend to pull out when the time is right.

1. Tell me about your worst relationship.

Again, it's good to wrap your head around your partner's dating history. But diving in too soon is a mistake.

Remember that people usually cast themselves as victims, so pay attention to inconsistencies.

2. What past relationship did you mess up?

Nobody is perfect, and if someone has been dating for a while, they've likely messed up a relationship — or seven.

When someone can be honest about what they've done wrong in the past, that's an excellent sign.

3. What would you do if you didn't hear from me for 48 hours?

This line of questioning will give you an idea of how the man you're dating feels about you. If he thinks the relationship is casual, he may not do anything.

After all, two days of not talking isn't a huge deal. But if he's serious about you, it's a long time not to talk. 

4. Would you marry someone who wasn't the same [religion/ethnicity/et cetera]?

This is perfectly acceptable to ask after the third date. After all, if he wouldn't consider getting serious with you because of something you can't change, there's no point wasting your time in a dead-end romance.

5. How would you react if you ran into your childhood best friend?

Would it be cool? Is there unaddressed conflict still lingering between them? Inquiring minds want to know!

6. When do you think it's okay not to introduce someone you're with?

Pull this one out after you've been out and about together, and he failed to introduce you to someone he knew and bumped into. 

7. Are we in a friendship, situationship, or relationship?

Play it cool when you ask. The last thing you want is to come across as clingy.

Plus, the answer will give you a temperature reading on the relationship.

8. Do you think people make their luck? Or is it something bestowed?

If you're curious about his worldview regarding spirituality, fate, and similar concepts, ask him a question like this. 

9. Do you think men and women are fundamentally different?

People have strong opinions about gender. Uncover your man's positions with a question like this.

10. Where do you think you'd be if we had never met?

The correct answer, of course, is lonely and disheveled. (We kid.)

But if there's trouble in paradise, he may feel comfortable expressing his discontentment by answering a question along these lines.

Funny Trick Questions to Ask Your Boyfriend

The following questions are when you want answers but want to keep things light-hearted.

1. Do you think I'm beautiful, alluring, or hot?

This is a jocular way to determine how the guy you're dating sees you. If he says, “All three!” that's all the better.

2. If it came down to [name his pet] or me, how would you break the bad news to me?

Let him know you appreciate and respect his bond with his pet in a clever and confidently self-deprecating way. He'll love it. 

3. How much would you pay to ransom me from kidnappers? How much could you pay?

This is a fun question to ask after you've watched an action movie or thriller.

Not only will you get an idea of how much you mean to him, but you may gain insight into his financial situation (if he's honest). 

4. Would you rather eat your mother's food or mine?

Don't get upset if he chooses mom! Some men are genetically attached to their mother's meals.

It's what they know! But if he picks you, that's an excellent sign. (Just don't tell his mom!)

5. If I thought one of your friends was better looking than you, how would it make you feel?

This is a flirty question that will test his jealousy trigger. If he gets defensive, that's a clue to his vanity.

6. How old would the 12-year-old you think I was?

Talking about how we viewed the world as children can be hilarious. Start the conversation by throwing out this question.

7. Who was your favorite book character as a kid?

This may not be the best question if he's not the intellectual type. After all, you don't want to make him feel inferior.

8. When did you stop wetting your bed?

Bedwetting feels traumatic as a kid, but it can lead to funny childhood memories when older.

9. If Halloween was tomorrow, and we were going to a party, what costumes would we wear?

Don't be upset if he doesn't have a super answer. Just as some folks can't do quick math in their heads, some people can't think creatively on their feet.

10. What show do you watch that you'd never admit to your boys?

Everyone has guilty pleasure shows. That's why the reality market is massive!

Who knows, you may discover you're both big fans of the same obscure show.

Trick Questions for Him That You Should Never Ask 

We've looked at several dozen trick questions you can ask your boyfriend.

Now, let's turn our attention to the opposite side of the coin: What trick questions should you avoid like the plague?

Below are the ten questions you should never ask a lover if it's early in the relationship and the goal is to keep things fun (and a little mysterious).

  1. Did you have more sexual chemistry with your ex than with me?
  2. Who would you choose: your friends or me?
  3. When are you going to ask me to marry you!?
  4. What should we name our future kids?
  5. If you could date one of my friends, who would it be and why?
  6. Do you remember exactly where we had our first kiss?
  7. Why don't you love me? (If he does and you've been together for a while)
  8. What would you do if I died? How long would it take you to move on?
  9. Do I look fat? Pretty?
  10. Do you think I'm smart?

Final Thoughts

Again, basing a relationship on head games isn't wise; doing so will cause the partnership to crash and burn. But asking tricky questions is okay.

They can reveal a lot about where the relationship is, how your boyfriend feels about it, and how well you know each other.

But try not to take it too seriously. Ultimately, trick questions are meant to be light-hearted. Then again, a red flag is a red flag. So pay attention to glaring problem signals. 

Dating: It's so complicated! And we wish you every bit of luck.