Looking to add some fun and excitement to your relationship? Delving into a set of intriguing and playful trick questions can be an entertaining way to get to know your boyfriend better. In this blog post, we’ve curated a list of 100 trick questions to ask your boyfriend that are guaranteed to spark laughter, deep conversations, and maybe even a few surprises.
From lighthearted questions to learning about his past to thought-provoking hypothetical scenarios, there’s something for every couple to enjoy. Whether you’re on a road trip, enjoying a cozy night in, or simply looking for a new way to connect, these questions offer a delightful blend of humor and insight.
So, grab a glass of wine, get your significant other by your side, and let’s dive into the world of 100 trick questions to ask your boyfriend!
20 warm-up trick questions to ask your boyfriend
1. If you could be one other person for a day, who would it be and why?
2. What is the one thing you would never do even if someone paid you a million dollars?
3. If you could switch places with any animal, which one would it be and why?
4. What’s the weirdest dream you’ve ever had?
5. Which of your friends is the worst influence on you?
6. What constitutes cheating in a relationship to you?
7. If someone gave you a time machine, where and when would you go first?
8. Do you think there’s a difference between emotional and physical infidelity?
9. What’s your biggest red flag that I should know about?
10. What’s one skill you wish you had but don’t have?
11. If you could have dinner with any three people, living or dead, who would they be, and why?
12. Which of your friends treats their partner the worst? Is it behind their back or to their face?
13. Would you rather be famous for something good or notorious for doing something bad?
14. Which of my friends are you most attracted to and why?
15. Do you believe in soulmates? Why or why not?
16. What would you do if I got jealous of your best friend?
17. Do you think money can buy happiness?
18. Would you rather do a job you hated but paid well or a job you loved but paid poorly?
19. What’s your biggest ick?
20. Would you rather be the funniest person in the room or the smartest?
These warm-up trick questions to ask your boyfriend are perfect for breaking the ice and getting to know each other on a deeper level. You can start by taking turns answering these questions on a date night or during a long car ride. They are perfect for relaxing into the deeper conversations that will come with the rest of the questions.
20 trick questions to ask your boyfriend about his dating history
1. Have you ever had your heart broken? If so, what happened?
2. Have you ever cheated on a significant other?
3. What’s the worst thing you’ve ever lied about to an ex-partner?
4. What’s the craziest thing you’ve done for love?
5. Have you ever ghosted someone after sleeping with them?
6. What’s the biggest lesson you’ve learned from your past relationships?
7. How many people have you said “I love you” to?
8. And how many have you actually been in love?
9. Is there anyone from your past that I should know about?
10. Have you ever got with a friend’s ex behind their back?
11. Do you have a typical first date that you take all your dates on? If so, what is it and why?
12. Have you ever settled with someone because they were really attractive even though you had nothing in common?
13. Is there a compliment you always give to people that you don’t really mean but it makes them more likely to go home with you?
14. Have you slept with any of your friends that I know?
15. How comfortable would you be if I had a long conversation with your ex?
16. Which of your exes did your family and friends like the most and why?
17. Can you tell me about the time you lost your virginity?
18. What’s the most romantic thing someone has done for you?
19. What’s the best sex you’ve ever had?
20. If you could message one thing to one of your exes, who would it be, and what would you say?
These trick questions to ask your boyfriend about his past relationships can give you a deeper understanding of his dating history and what he has learned from it. It’s important to approach these questions with an open mind and not judge him for his past experiences. It’s natural for people to have a past, and while it’s interesting to learn about, it’s important to focus on the present and future of your relationship. If there are any red flags or concerns that come up, communicate openly and honestly with your partner.
20 trick questions to ask your boyfriend about your relationship
1. What’s one thing you would change about me?
2. If I died, how long would you wait before you replaced me?
3. Have you ever lied to me?
4. Do I have any annoying habits that you’ve forced yourself to tolerate?
5. Who do you think is punching above their weight in this relationship?
6. If you could change one thing about our relationship, what would it be?
7. Is there anything you feel we need to discuss or address about our relationship?
8. What was your first impression of me? Has it changed since we started dating?
9. What’s the biggest sacrifice you’ve made for our relationship?
10. Do you see marriage and kids in our future?
11. How would you feel if I was friends with one of my exes?
12. Do you think we should tell each other if we’re in the presence of someone we’ve slept with?
13. What would you do if I said I didn’t want to be with you?
14. Do you feel like I’ve ever come across too strong or clingy?
15. Do you ever compare me to ex-partners?
16. Are there any insecurities you have about our relationship?
17. What was your biggest doubt about being in a relationship with me and how do you feel about it now?
18. What’s my better quality, my looks or my personality?
19. Who do you think loves each other more in our relationship?
20. If you could improve one thing about our sex life, what would it be?
Now that you have a deeper understanding of your boyfriend’s dating history, it’s time to dive into your relationship. These trick questions to ask your boyfriend about your relationship should actually be used as a way to strengthen your bond and communication. It’s important to approach these questions with honesty and vulnerability and be prepared for any answers that may come up. Remember, the key to a healthy relationship is open and honest communication. So use these questions as a way to learn more about each other and grow together as a couple.
20 trick questions to ask your boyfriend about his past
1. What was the most rebellious thing you did as a teenager?
2. Have you ever had a strange or funny nickname?
3. What is one thing you regret doing in the past?
4. Have you ever been arrested or gotten into trouble with the law?
5. Have you ever had a crazy roommate or housemate? What was the experience like?
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?
7. What’s the most thoughtful gift you’ve ever received, and why was it meaningful to you?
8. Do you have any people you used to be friends with that cut you out of their life? If so, what did you do to deserve that?
9. What’s the most embarrassing thing your parents caught you doing as a kid?
10. If you could go back in time, what advice would you give your younger self?
11. What was the biggest lesson you learned from your teenage years?
12. Have you ever done something illegal? If so, what was it and why did you do it?
13. Were you ever in a fight or physical altercation? How did it happen and what was the outcome?
14. If you could relive one moment from your past, what would it be and why?
15. Have you ever had a near-death experience? What happened?
16. Do you have any regrets about your education or career choices?
17. What’s the most rebellious thing you’ve done as an adult?
18. What’s the craziest thing you’ve done while under the influence of alcohol or drugs?
19. How have your past experiences shaped who you are today? Overall, do you think they were positive or negative influences?
20. What’s the biggest secret you’ve ever kept from your family or friends?
Asking your boyfriend these trick questions about his past can give you a better understanding of who he is as a person and what experiences have shaped him. It’s important to approach these questions with sensitivity and without judgment, as everyone makes mistakes and has regrets. Use these questions as a way to connect on a deeper level and learn more about each other’s pasts. Remember, the past does not define someone’s present or future, but it can provide valuable insights into their character and journey.
20 trick questions to ask your boyfriend about his future
1. What’s your ultimate dream job?
2. Where do you see yourself living in 10 years?
3. Do you want to travel the world or settle down in one place?
4. How many kids would you like to have, if any?
5. What is one thing on your bucket list that you haven’t done yet?
6. If money wasn’t a factor, what would you do with your life?
7. Do you have any specific career goals? If so, what are they?
8. Talk me through your five-year plan. What do you want to achieve, and where exactly do you see your life in five years’ time?
9. Where do you see yourself in terms of personal growth and development in the next five years?
10. What’s something new you want to try or learn in the future?
11. How important is it for you to have a work-life balance in the future?
12. What do you think makes a successful relationship and how will we maintain that in the future?
13. Do you have any specific plans for retirement or your golden years?
14. How do you see our relationship evolving in the next few years?
15. Are there any major changes or decisions that you want to make in the future?
17. How do you envision your future family and what role would you play in it?
18. Do you have any financial goals for the future? If so, what are they?
19. What’s one thing you hope to accomplish before turning 40?
20. If you could be remembered for one thing, what would it be and why?
Asking your boyfriend about his future plans and goals can help you understand his aspirations and desires. These trick questions can also provide you with more clarity on where your relationship fits his long-term plans. Does he mention you in his future, or does he talk about a future with someone in a more general sense? This can give you valuable insights into his commitment to the relationship and if you are both on the same page. So go ahead, ask these trick questions, and see where they take your conversations about the future.
Final thoughts
Communication is key in any relationship, and asking these trick questions can open up new channels for deeper conversations and understanding. Remember to approach them with honesty, vulnerability, and an open mind. While tricking your partner into revealing personal information may seem fun, these questions should not be used as a means of manipulation or to create trust issues. Use them as a way to connect and learn more about each other in a healthy and respectful manner. They can provide you with an opportunity to strengthen your bond and grow together as a couple. So go ahead, ask your boyfriend these trick questions, and see where they take your relationship.
Now you’ve tricked your boyfriend and had some fun, why don’t you turn up the heat with our 100 dirty questions to ask your boyfriend.
