100 Questions to Ask Your Boyfriend to Test His Love

By: Milena J. Wisniewska

His love seems real, but those sneaky doubts still bother you like a pebble in a shoe, messing with your perfect love story. 

It’s time to kick those uncertainties to the curb with a few well-placed questions revealing the true depth of his affection and maybe even discovering a few surprises along the way. 

Table of Contents

Questions to Ask Him to See If He Really Loves You

Does he love you or is he just here for the snacks? Asking questions is the only way to know. 

With these 25 deep questions, you’ll uncover whether he sees you as just a side of fries — fun and enjoyable but not the main feast — or if he understands that you’re the whole meal. 

  1. What was your first impression of me, and how has it evolved?
  2. What qualities do you admire most about me?
  3. What’s the biggest lesson you’ve learned from me?
  4. What’s your most cherished memory of us together, and why?
  5. What’s the most romantic thing I’ve ever done for you?
  6. Is there a song that makes you think of us, and why?
  7. When we’re apart, what emotions do you experience?
  8. How does our love feel to you?
  9. How do you feel when I achieve something great?
  10. What goes through your mind after we fight or disagree?
  11. How do you show your love for me daily?
  12. How do you like me to show you my love daily?
  13. Where do you see our life together in the next ten years?
  14. How do you envision supporting me through my dreams and goals?
  15. How do you envision me supporting you through your dreams and goals?
  16. How do you see us growing together as individuals and as a couple?
  17. What are your thoughts on starting a family?
  18. What’s the most crucial area we need to work on?
  19. What’s the biggest challenge we’ve overcome, and how did it shape us?
  20. Do you ever experience feelings of jealousy or insecurity in our relationship?
  21. What sacrifices have you made for our relationship, and how do they make you feel?
  22. What does commitment mean to you in our relationship?
  23. Can you describe a moment when you felt truly connected to me?
  24. What are your thoughts on forgiveness and how it applies to us?
  25. How do you prioritize our relationship amidst other responsibilities?

These are hard questions to ask but they will let you get a better understanding of the depth of your emotional intimacy and verify whether you are both on the same page. 

A study in the Personality and Social Psychology Bulletin shows that by discussing memories, feelings, future goals, and daily love gestures, couples can strengthen their bond, making each partner feel valued and understood, ultimately enriching their relationship.[1]

After all, if you don’t share the same long-term relationship vision, it makes sense not to waste any more time, right?

Trick Questions to Ask Your Boyfriend to See If He Loves You

He’s halfway through a mountain of ironing, completely zoned out, when you casually ask, “If you had to pick between me and your favorite hobby, which would you choose?” 

Catching him off guard can yield the most honest and spontaneous, often hilarious responses. These 25 trick questions are perfect for revealing his true feelings!

  1. If I turned into a cartoon character for a day, who would you hope I become?
  2. Would you still like me if I had a third eye in the middle of my forehead?
  3. If I suddenly developed the ability to talk to animals, which animal would you be most worried about me befriending?
  4. If you could swap lives with me for a day, what’s the first thing you’d do?
  5. Would you still love me if I had to wear a clown costume everywhere we went for a month?
  6. Would you rather have me always whisper or always shout?
  7. Would you still like me if I decided to become a professional mime?
  8. Would you still like me if my laugh sounded like a foghorn?
  9. Would you still love me if I spontaneously started speaking in Shakespearean English all the time?
  10. If I insisted on wearing socks with sandals, would you still be seen in public with me?
  11. Would you help me bury a body if I accidentally ran over a garden gnome?
  12. If we had to relive one day over and over, which day would you choose?
  13. Would you let me name our first pet after a character from my favorite TV show?
  14. Would you still like me if I started dressing like a character from the 1980s?
  15. If I challenged you to a dance-off in the middle of the grocery store, would you participate?
  16. Would you rather I have a permanent duck face or constantly do the robot when I walk?
  17. If I decided to take up yodeling as a hobby, would you support me?
  18. If I painted our bedroom neon green without consulting you, how would you react?
  19. Would you switch places with me for a day if it meant you had to wear high heels the whole time?
  20. If I insisted on doing all the grocery shopping while wearing a superhero costume, would you join me?
  21. Would you rather I always smelled like your least favorite food or sounded like your least favorite celebrity?
  22. Would you still like me if I could only tell dad jokes for an entire month?
  23. Would you rather I had an uncontrollable urge to photobomb strangers or make awkward small talk with everyone we meet?
  24. If I decided to take a vow of silence for a week, how would you communicate with me?
  25. If I replaced all our furniture with bean bag chairs, how long would you last before replacing them?

So, channel your inner Phoebe Buffay and unleash these delightfully random, tricky, and fun questions on him! 

His answers will be a mix of honesty and hilarity. 

Just like Phoebe’s peculiar yet undeniable charm, these questions will reveal just how deep his love — and patience — truly runs. Could he be your lobster?

Romantic Questions to Ask Your Boyfriend to Test His Love

Sitting under the twinkling stars on a breezy summer night is a great time for this 25-item romantic questionnaire to test his love. 

  1. What was your impression of me after our first date?
  2. How would you describe our first kiss?
  3. When did you realize you were in love with me?
  4. How do you feel when I say “I love you”?
  5. What’s your favorite thing about my personality?
  6. What’s the sweetest thing I’ve ever done for you?
  7. What’s the most memorable date we’ve had?
  8. What’s the most romantic place we’ve been together?
  9. What’s one thing you’ve always wanted to do together?
  10. How do you see our love evolving over the years?
  11. How do you feel when you see me after a long day?
  12. How do you feel when we hold hands?
  13. How do you feel when we cuddle?
  14. How do you feel when we dance together?
  15. What makes you feel loved in a relationship?
  16. How do you express your love for me without words?
  17. What’s your favorite way to spend time with me?
  18. What’s your favorite way to say “I love you”?
  19. What’s the most romantic thing you’d like to do for me?
  20. How do you feel about celebrating anniversaries?
  21. What’s your idea of a perfect romantic evening?
  22. What’s the most thoughtful gift you’ve ever given me?
  23. What song reminds you of me?
  24. How do you feel when I surprise you with something special?
  25. What’s the most romantic compliment I’ve ever given you?

According to Dr. Gary Chapman, author of The 5 Love Languages, regularly expressing love and affection through words and actions is essential for maintaining a healthy relationship. Romantic questions help to keep the spark alive and the love strong.[2]

However, a study published in PLOS ONE highlights that individuals with unresolved issues from past relationships or unrealistic expectations influenced by media portrayals of romance may feel uneasy with romantic gestures​​.[3]

So, keep this in mind when trying to ignite some romance; sometimes, it may feel awkward and uncomfortable not because he doesn’t like or love you, but due to his past experiences and learned behaviors about romance. 

As always, the best way to know is by asking thoughtful questions, listening attentively (reflective listening is my personal favorite), and communicating openly.

Questions to Ask Your Boyfriend to Test His Love Over Text

Thanks to the invention of instant communication, being apart doesn’t have to leave you hanging — these 25 playful and thought-provoking questions will help you gauge his feelings over text.

  1. What are your core values when it comes to love and relationships, and how do you apply them in our relationship?
  2. What’s the best piece of relationship advice you’ve ever received, and how do you apply it in our relationship?
  3. How do you feel when we spend quality time together?
  4. What’s one thing you appreciate most about our relationship?
  5. How do you feel when I flirt with you?
  6. What’s the most attractive thing about our relationship?
  7. What’s one quality you think makes our relationship unique?
  8. How do you think we complement each other as a couple?
  9. How do you feel about exploring new things together as a couple?
  10. What’s one thing you love about our communication style?
  11. What’s one thing you don’t love about our communication style?
  12. How do you think we’ve both grown since we started dating?
  13. What’s one thing you’re willing to work on to improve our relationship?
  14. What’s one thing you think we should try together to strengthen our bond?
  15. What’s your favorite memory of us so far?
  16. What’s the most intimate moment you remember sharing with me?
  17. What are your thoughts and feelings about our future together?
  18. What’s the funniest thing that’s ever happened on one of our date nights that you never told me about out of embarrassment?
  19. If we were characters in a comedy show, which show would it be and why?
  20. What’s one ridiculous thing you’d love to do with me just for fun?
  21. How do you feel about PDA (public displays of affection)?
  22. How do you feel about discussing your past relationships with me?
  23. How do you balance your personal goals with our relationship goals?
  24. What’s a past experience that significantly influenced your views on love and relationships, and how does it affect our relationship?
  25. What are your main priorities in life right now, and how do you see our relationship fitting into those priorities?

Texting can be a powerful way to stay connected and express love. 

It often encourages people to be bolder and more honest because it provides time to reflect, leading to more thoughtful and precise responses. 

By asking your boyfriend these questions over text, you can get the real answers — no need to resort to the old “loves me, loves me not” flower petal plucking!

Conclusion

In your quest to test your boyfriend’s love, asking thoughtful, revealing questions is key. 

Whether through direct, tricky, romantic, or text-friendly questions, you’ll gain deeper insights into his feelings, strengthen your bond, and ensure your relationship remains healthy and loving. 

And who knows, maybe he’ll start questioning you back. Are you ready for that?

Want more advice and tips about being in a relationship? Check out our page here!

FAQs

How can I test my boyfriend’s true love?

You can test your boyfriend’s true love by observing his actions and consistency over time, communicating openly about your needs and expectations, and seeing how he responds to challenging situations. Genuine love is shown through respect, support, and effort in the relationship.

What is the hardest question to ask your boyfriend?

The hardest question to ask your boyfriend is often about the future of your relationship. Asking “Where do you see our relationship going?” can be difficult but necessary for understanding his long-term intentions and commitment.

How can I communicate better?

To communicate better, practice active listening, express your thoughts clearly and respectfully, and use “I” statements to share your feelings without blaming. Regularly check in with each other to ensure mutual understanding and address any issues promptly.

References

  1. Aron, A., Melinat, E., Aron, E. N., Vallone, R. D., & Bator, R. J. (1997). The experimental generation of interpersonal closeness: A procedure and some preliminary findings. Personality and Social Psychology Bulletin, 23(4), 363–377.
    https://doi.org/10.1177/0146167297234003 ↩︎
  2. Chapman, G. (1992). The 5 love languages: The secret to love that lasts. Northfield Publishing. ↩︎
  3. Fraley, R. C., & Shaver, P. R. (2016). Regulation of romantic love feelings: Preconceptions, strategies, and feasibility. PLOS ONE, 11(8), e0161087.
    https://doi.org/10.1371/journal.pone.0161087 ↩︎




Author

  • Milena J. Wisniewska

    Milena might not be a relationship professor, but she's definitely been through it all, learned her lessons, and is here to spill the tea.She combines the wisdom of renowned relationship specialists with her own romantic adventures to offer relatable and practical advice.

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