Trick Questions to Ask Your Boyfriend

Relationships are all about getting to know each other better, and asking questions is a great way to do that. However, sometimes you might want to spice things up a bit and ask some trick questions to keep your boyfriend on his toes. Here are some fun and challenging trick questions to ask your boyfriend:

1. If you could only choose one, would you rather have a million dollars or true love?

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This question is a classic dilemma. It will reveal whether your boyfriend is more interested in material possessions or emotional connections. Of course, there is no right or wrong answer, but it’s fun to see what your boyfriend values most.

2. What would you do if you won the lottery?

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This question is a great way to find out what your boyfriend’s dreams and aspirations are. It will give you a glimpse into his priorities and what he would do with a sudden influx of wealth.

3. If you could have any superpower, what would it be and why?

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Everyone dreams of having a superpower, and this question will show you what your boyfriend’s inner child desires. You can also ask follow-up questions about how he would use his powers and what kind of superhero he would be.

4. If you could live in any time period, which one would you choose and why?

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This question will reveal your boyfriend’s interests and what he finds fascinating about history. You can also ask follow-up questions about what he would do in that time period and how he would adapt to the lifestyle of that era.

5. What is the craziest thing you’ve ever done?

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This question will give you some insight into your boyfriend’s wild side. It’s a great way to bond over shared experiences or laugh about some of the crazy things you’ve done in the past.

6. If you could have any job in the world, what would it be?

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This question will reveal your boyfriend’s career aspirations and what kind of work he finds fulfilling. You can also ask follow-up questions about why he chose that job and what he would do if he couldn’t have that job.

7. What is your biggest fear?

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This question will show you what your boyfriend is afraid of and how he deals with fear. It’s a great way to have a deep conversation and find out what makes him tick.

8. If you could travel anywhere in the world, where would you go?

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This question will reveal your boyfriend’s wanderlust and what kind of destinations he finds appealing. You can also ask follow-up questions about what he would do in that location and why he chose that specific place.

9. What is your favorite childhood memory?

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This question will show you what your boyfriend cherishes from his past and what kind of experiences shaped him into the person he is today. It’s a great way to bond over shared childhood experiences or learn something new about each other.

10. If you could only eat one type of food for the rest of your life, what would it be?

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This question will reveal your boyfriend’s culinary preferences and what kind of flavors he enjoys. You can also ask follow-up questions about why he chose that food and how he would deal with the monotony of eating the same thing every day.

11. What is the most embarrassing thing that has ever happened to you?

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This question will show you what your boyfriend considers embarrassing and how he deals with awkward situations. It’s a great way to bond over shared embarrassing moments or laugh about his mishaps.

12. If you could only listen to one musician or band for the rest of your life, who would it be?

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This question will reveal your boyfriend’s musical taste and what kind of artists he enjoys. You can also ask follow-up questions about why he chose that musician or band and how he would deal with the monotony of listening to the same music all the time.

13. What is your favorite book or movie?

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This question will show you what your boyfriend likes to read or watch and what kind of stories he finds compelling. You can also ask follow-up questions about why he chose that book or movie and what he likes about the story.

14. What is the most adventurous thing you’ve ever done?

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This question will reveal your boyfriend’s sense of adventure and how willing he is to take risks. It’s a great way to bond over shared experiences or learn something new about each other.

15. If you could switch lives with anyone for a day, who would it be and why?

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This question will reveal your boyfriend’s interests and what kind of lifestyle he finds appealing. You can also ask follow-up questions about why he chose that person and what he would do if he were in their shoes.

16. What is your favorite thing about me?

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This question will show you what your boyfriend appreciates about you and what kind of qualities he values in a partner. It’s a great way to strengthen your bond and feel appreciated.

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

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This question will reveal your boyfriend’s self-awareness and what kind of changes he would like to make in his life. You can also ask follow-up questions about why he chose that aspect of himself and how he plans to work on it.

18. What is your favorite hobby or pastime?

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This question will show you what your boyfriend likes to do for fun and what kind of activities he finds enjoyable. You can also ask follow-up questions about why he chose that hobby and how he got into it.

19. If you could go back in time and change one thing, what would it be?

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This question will reveal your boyfriend’s regrets and what kind of experiences he wishes he could change. You can also ask follow-up questions about why he chose that moment and how he thinks his life would be different if he could go back and change it.

20. What is your biggest pet peeve?

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This question will show you what your boyfriend finds annoying and how he deals with frustration. It’s a great way to learn how to avoid irritating behavior and how to communicate more effectively.

21. What is the most romantic thing you’ve ever done for someone?

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This question will reveal your boyfriend’s romantic side and what kind of gestures he finds meaningful. You can also ask follow-up questions about why he chose that moment and how he plans to continue being romantic in the future.

22. If you could only have one type of pet, what would it be?

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This question will reveal your boyfriend’s love for animals and what kind of pets he finds appealing. You can also ask follow-up questions about why he chose that type of pet and how he would take care of it.

23. What is your favorite holiday and why?

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This question will show you what your boyfriend finds enjoyable about different holidays and how he likes to celebrate. You can also ask follow-up questions about his favorite traditions and how he plans to celebrate in the future.

24. If you could live anywhere in the world, where would it be?

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This question will reveal your boyfriend’s wanderlust and what kind of locations he finds appealing. You can also ask follow-up questions about why he chose that place and how he plans to adapt to the lifestyle there.

25. What is your favorite type of cuisine?

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This question will reveal your boyfriend’s culinary preferences and what kind of flavors he enjoys. You can also ask follow-up questions about his favorite dishes and how he likes to cook.

26. What is your favorite song or album?

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This question will show you what your boyfriend likes to listen to and what kind of music he finds enjoyable. You can also ask follow-up questions about why he chose that song or album and what he likes about the artist.

27. If you could be any fictional character, who would it be and why?

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This question will show you what your boyfriend finds fascinating about different characters and how he identifies with them. You can also ask follow-up questions about why he chose that character and what he would do if he were in their shoes.

28. What is your favorite memory of us together?

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This question will show you what your boyfriend cherishes about your relationship and what kind of moments he finds memorable. It’s a great way to strengthen your bond and feel appreciated.

29. If you could have any car in the world, what would it be?

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This question will reveal your boyfriend’s love for cars and what kind of vehicles he finds appealing. You can also ask follow-up questions about why he chose that car and how he would maintain it.

30. What is your favorite thing about yourself?

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This question will show you what your boyfriend values about himself and what kind of traits he finds admirable. It’s a great way to boost his self-esteem and learn something new about him.

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