155 Trick Questions to Ask Your Boyfriend & Get to Know Him Better

Looking to learn more about your boyfriend and his feelings toward your relationship? Asking trick questions is the perfect way to start a meaningful conversation and strengthen your connection. In this article, we’re providing the ultimate list of trick questions to ask your boyfriend so you can understand him on a deeper level (without putting him on the spot). So, if you’re ready to discover new things about each other, read on!

Section 1 of 7:

Casual Trick Questions to Ask Your Boyfriend

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Start off with easy questions to get to know your boyfriend better. Not in the mood for a deep discussion? Ask some fun and lighthearted “trick” questions to pass the time! No matter how long you’ve been dating, there’s always more to learn about your partner, and by expressing interest in his personal preferences and behavior, you show that you care about him.^{[1]
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- What’s your death row meal?
- What’s your biggest pet peeve?
- Do you have any hidden talents?
- What’s your dream vacation spot?
- What’s one skill you wish you had?
- What’s your favorite way to unwind?
- What’s your most prized possession?
- Do you prefer staying in or going out?
- What’s the greatest character of all time?
- What’s the weirdest dream you’ve ever had?
- If you could date any celebrity, who would it be?
- If you could pick a new name for me, what would it be?
- If you could have any superpower, what would you pick?
- If I asked you to jump, would you ask “how high” or “why?”
- If you won the lottery, what’s the first thing you would buy?
- If I had an identical twin, how would you know it’s really me?
- Would you rather always win an argument or never argue at all?
- Would you rather be the funniest or smartest person in the room?
- If you could be another person for a day, who would it be and why?
- If you could live in any fictional world, which one would you choose?
- If someone gave you a time machine, what decade are you going to?
- If you could only say one word for the rest of your life, what would it be?
- If you could have dinner with 3 people, dead or alive, who would they be?
- What would save first if your house was on fire: me, the dog, or your computer?
- Out of the two of us, who would be more likely to survive a zombie apocalypse?
- If you had to relive the same day over and over, which day would it be and why?

Section 2 of 7:

Funny Trick Questions to Ask Your Boyfriend

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Throw in silly questions to make your boyfriend laugh out loud. If he’s feeling down, asking him funny questions can brighten his mood. Whether you reference an inside joke or bring up something completely out of pocket, sharing a laugh can deepen your bond and improve your relationship as a couple.^{[2]
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- What’s your most useless skill?
- What’s your biggest irrational fear?
- What’s the best prank you’ve ever pulled?
- Would you rather be 3 feet shorter or taller?
- Would you still love me if I turned into a worm?
- Would you rather be bald or have no eyebrows?
- What’s the most embarrassing thing in your room?
- Would you rather always shout or always whisper?
- What’s the funniest thing you believed in as a child?
- If you could fight any historical figure, who would it be?
- What’s the worst text you’ve sent to the wrong person?
- What’s the most unnecessary white lie you’ve ever told?
- What celebrity would be the worst leader of our country?
- What inanimate object would you delete from existence?
- What’s the weirdest thing you’ve seen in someone’s house?
- What’s the best excuse you’ve given to skip school or work?
- What’s an embarrassing song or band that you secretly love?
- When’s the most inappropriate time you've laughed at something?
- What’s the cringiest thing you’ve done to get someone’s attention?
- Would you rather fight 100 second graders or a bear with shark arms?
- Would you rather clog the toilet on the first day or work or on a first date?
- Would you rather show me embarrassing school photos or your search history?
- Would you rather always feel like you have to sneeze or sneeze 500 times a day?
- Would you rather have your ringtone be someone screaming or someone cursing?
- Would you rather be covered in tattoos from head to toe or have one giant face tattoo?

Section 3 of 7:

Flirty & Spicy Trick Questions to Ask Your Boyfriend

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Create tension with these fun and flirty “trick” questions. If you really want to put your boyfriend in the hot seat, ask about his fantasies and turn-ons. It’s a great way to catch him off guard, crank up the heat, and make him feel desired.^{[3]
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- What’s your usual type?
- What’s your biggest turn-on?
- What’s your ultimate fantasy?
- What’s your favorite way to kiss?
- What song gets you in the mood?
- Do you prefer kissing or cuddling?
- Do you think you’re a good kisser?
- What was your sexual awakening?
- Who has the nicer butt, me or you?
- What outfit do I look the sexiest in?
- What’s your biggest guilty pleasure?
- Have you ever fantasized about me?
- How would you describe our first kiss?
- What’s your favorite place to be kissed?
- Out of the two of us, who has more rizz?
- What’s the best pick-up line you’ve used?
- How often do you think about kissing me?
- Have your parents ever walked in on you?
- Would you ever go skinny dipping with me?
- What’s the most attractive physical feature?
- How would you approach me if we weren’t dating?
- Did you stalk me on social media before we dated?
- Do you prefer being the big spoon or the little spoon?
- What’s the first thing that comes to mind when you think of me?
- If we were trapped in a dark and empty room, what would you do?
- If we switched bodies for a day, what’s the first thing you would do?

Section 4 of 7:

Love-Related Trick Questions to Ask Your Boyfriend

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Figure out how your boyfriend shows love to maintain a strong bond. If you want to connect with your boyfriend on a deeper level, ask him how he feels about your relationship. What’s his idea of the perfect date? Does he prefer verbal or physical affection? Is there anything you can do to be a better partner? According to matchmaker Erika Kaplan, it’s important to “communicate what you need in a relationship” since “people receive and give love in different ways.”
- What’s your love language?
- How often do you think of me?
- How did you know I was into you?
- Do you believe in love at first sight?
- What’s your idea of the perfect date?
- Would you rather have no kids or 10 kids?
- What’s something that reminds you of me?
- What are your green flags in a relationship?
- What’s the first thing you noticed about me?
- What do you appreciate the most about me?
- What’s your favorite memory of the two of us?
- When did you realize you had feelings for me?
- What’s your take on age gaps in relationships?
- What do your friends and family think about me?
- If we had a Netflix show, what would it be called?
- What’s your favorite thing about our relationship?
- Do you prefer physical or non-physical compliments?
- Would you be jealous if you saw me with other guys?
- What’s one thing I can do to improve our relationship?
- If you could describe me in one word, what would it be?
- Is there a new hobby or activity you want to try together?
- If we formed a band, what kind of music would we make?
- Do you prefer grand romantic gestures or small surprises?
- Would you rather live in a tiny home with me or a mansion?
- If we had to move to another country, where would we live?
- If you could relive one day in our relationship, what would it be?

Section 5 of 7:

Relationship-Related Trick Questions to Ask Your Boyfriend

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Ask about his previous relationships to see how compatible you are. While bringing up exes can be awkward at first, it’s a great way to find out what type of partner your boyfriend is and deepen your connection.^{[4]
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Go to source} You can discuss his dating history, communication style, and overall perspective on love, but be sure to respect his boundaries if he doesn’t feel comfortable opening up. As a general rule, don’t ask things you aren’t willing to answer yourself.
- Have you ever been in love?
- Do you regret dating anyone?
- What’s your definition of love?
- Do all of your exes look similar?
- How would you define cheating?
- Have you ever ghosted anybody?
- Why did your last relationship end?
- How many people have you dated?
- Have you ever cheated on someone?
- What age did you have your first kiss?
- Have you ever had your heart broken?
- Are you still friends with any of your exes?
- Would you ever date your best friend’s ex?
- Do you consider yourself a romantic person?
- Did you or your ex end your last relationship?
- What’s the craziest thing you’ve done for love?
- What do you miss the most about being single?
- What was your favorite thing to do with your ex?
- Have you kissed any of your friends that I know?
- What are your non-negotiables in a relationship?
- How do you handle conflict in your relationships?
- How many serious relationships have you been in?
- Is there anyone from your past that I should know about?
- Before dating me, did you prefer being single or in a relationship?
- How long did it take for you to move on from your last relationship?
- What’s the biggest lesson you’ve learned from your previous relationships?
- Would you rather be cheated on and never know, or cheat and have your partner find out?

Section 6 of 7:

Deep Trick Questions to Ask Your Boyfriend

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Delve into deeper questions to learn about his character and values. If you want to strengthen the bond in your relationship, ask your boyfriend personal questions that move beyond the surface—and prepare to do the same. Asking about his dreams, fears, goals, and beliefs is one of the best ways to build trust and feel close to your partner.^{[5]
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- What’s your greatest fear?
- What’s your top goal in life?
- Are you close to your family?
- What’s your idea of success?
- What’s your biggest insecurity?
- When’s the last time you cried?
- What are you most grateful for?
- What are you the most proud of?
- Who do you look up to the most?
- Do you believe in fate or free will?
- Do you care what people think of you?
- Where do you see yourself in 5 years?
- What’s your favorite childhood memory?
- Do you think money can buy happiness?
- How have you changed in the past year?
- What are 3 things you love about yourself?
- Do you think physical or emotional pain is worse?
- Would you rather have more time or more money?
- What’s something you’ve never told anyone before?
- What’s the biggest misconception people have about you?
- What’s one thing you would do if there were no consequences?
- If you could change one thing about your past, what would it be?
- Would you rather be able to look into the future or change the past?
- If your life was a book, what’s the title of the chapter you’re in right now?
- Would you rather know the cause of your death or the date of your death?

Section 7 of 7:

Frequently Asked Questions

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1
What is the hardest question to ask your boyfriend? Asking a hard question may feel uncomfortable at first, but it allows you to learn more about your boyfriend, share meaningful conversations, and see if you’re compatible in the long run. Here are some of the hardest Qs:^{[6]
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- How much do you trust me?
- Why do you think people cheat?
- How do you set boundaries with someone?
- What do you fear the most about our relationship?
- Do you think it’s okay to tell white lies in a relationship?
- What social or political issues are most important to you?
- What’s the hardest experience you’ve ever gone through?
- How do you know when you’re really comfortable with someone?
- What do you think is the key to a healthy and happy relationship?
- How do you think responsibilities should be divided in a marriage?
2
Do trick questions work for long-distance relationships? Yes, asking trick questions is a great way to keep the romance alive! Plan a cute date night over FaceTime or Zoom, and take turns asking trick questions to have fun and strengthen your connection.^{[7]
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- If you’re asking trick questions over text, dating coach and matchmaker Laura Bilotta recommends using emojis to “add a playful tone to your messages” or “help convey your sense of humor.” For example, you could text “What’s your ultimate fantasy? 😈”
3
How do I choose the right trick question for my boyfriend? Think about his personality, your relationship dynamic, and the current mood. If it takes him a while to open up, for example, you might start with a funny or flirty question before moving on to deeper ones. You can also tweak any of our questions to match his interests, hobbies, and sense of humor. The goal is to ask questions that make him laugh, challenge his thoughts, and learn more about him.^{[8]
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- If you’re unsure whether you’re overstepping boundaries, preface the question by saying it’s okay not to respond if he feels uncomfortable.
4
Why is it important to ask your boyfriend questions? It allows you to deepen your connection, keep the spark alive, and build trust and intimacy in your relationship. Asking deep questions can teach you the best ways to show love to your partner, plus help you determine if you’re compatible in the early stages of dating.^{[9]
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- You can also take our love language quiz to find out how your partner prefers to give and receive affection.