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Getting to know your boyfriend on a deeper level doesn’t always have to happen during long, serious conversations in person. Sometimes, it’s fun to ask him interesting or playful questions over text that reveal more about who he is, what he thinks about, and what really matters to him. Whether you’re looking to laugh at some quirky memories or dive into more meaningful topics, asking truth questions can help you connect in a casual, laid-back way.

These questions are perfect for those moments when you want to switch things up and learn something new about him: whether it’s his past, dreams, or even his thoughts on relationships. I love how texting opens up an easy way to ask these kinds of questions, especially when you’re not together but still want to feel close.

In this post, I’ve put together 50 truth questions that range from fun and lighthearted to deep and thoughtful. Whether you want to know about his childhood memories, relationship preferences, or goals for the future, these questions will help you uncover more layers and strengthen your bond. Ready to get started? Let’s see what truths he’s willing to share!

Fun Truth Questions To Ask Your Boyfriend Over Text

Sometimes it’s fun to ask random questions that reveal something unexpected. These are light-hearted questions that can help you learn more about your boyfriend’s quirky habits or fun stories without getting too serious.

1. What’s the weirdest food you’ve ever tried?
2. What’s a silly nickname you’ve had growing up?
3. What’s the most embarrassing thing you’ve done in front of someone you liked?
4. If you could be a character in any TV show, who would you be?
5. Have you ever worn something just because you thought it looked cool, but you secretly hated it?
6. What’s the strangest gift you’ve ever received?
7. Do you have a secret talent that most people don’t know about?
8. What’s your go-to karaoke song, even if you’re a terrible singer?
9. If you could eat one thing for the rest of your life, what would it be?
10. What’s the worst haircut you’ve ever had?

Relationship Truths To Ask Your Boyfriend Over Text

These questions are great for learning more about how he feels about relationships and his thoughts on love. They’re not too deep, but they can still help you understand him better and see what matters most to him.

11. What’s something small I do that makes you happy?
12. Have you ever been in love before?
13. Do you believe in soulmates, and why or why not?
14. What’s your favorite thing about being in a relationship?
15. Is there something you’ve always wanted to do together but haven’t mentioned yet?
16. Do you think love is more about feelings or actions?
17. How did you know you wanted to date me?
18. Have you ever had a crush on someone you couldn’t be with?
19. What’s the most romantic thing you’ve ever done?
20. What’s your biggest relationship dealbreaker?

Deep Truths To Ask Your Boyfriend Over Text

These questions can help you dive a little deeper into his thoughts and feelings. They’re great for when you’re looking to have a more meaningful conversation and get to know him on a different level.

21. What’s something you wish more people understood about you?
22. What’s the hardest lesson you’ve learned in life so far?
23. If you could change one thing about yourself, what would it be?
24. What’s a fear you’ve had to overcome?
25. What’s something you’ve always wanted to ask me but never have?
26. How do you usually deal with stress?
27. Is there a dream you’ve let go of, and why?
28. What’s the best decision you’ve ever made?
29. What’s one thing you want to accomplish in the next five years?
30. Is there something you’re afraid to tell me?

Questions About His Past

These questions can help you learn more about his background and the experiences that shaped him. They’re not too intense, but they give insight into his past and what’s made him who he is today.

31. What’s a childhood memory that makes you smile every time?
32. Did you have a favorite toy or game when you were younger?
33. What’s the best trip you’ve ever been on?
34. Who was your first crush, and what happened?
35. What’s the biggest trouble you got into as a kid?
36. Did you ever sneak out or break the rules as a teenager?
37. Who was your best friend growing up, and are you still close?
38. What’s something from your past that you wish you could change?
39. What’s a skill you learned as a kid that you still use today?
40. How would your younger self feel about the person you are now?

Questions About His Dreams and Aspirations

These questions help you get a sense of what he hopes for in the future. It’s fun to learn more about his goals and dreams, and it also shows how he sees his future unfolding.

41. If money wasn’t an issue, what would you do for a living?
42. What’s one thing you’ve always wanted to try but haven’t yet?
43. Where do you see yourself living in five years?
44. What’s your biggest dream in life right now?
45. Do you think you’ll ever want to start a family?
46. What’s something you’ve always wanted to learn how to do?
47. If you could travel anywhere in the world tomorrow, where would you go?
48. What’s something you want to be remembered for?
49. Do you think it’s more important to work hard or to work smart?
50. What’s a goal you’re really proud of achieving?