77 Jaw-Dropping Questions to Ask Your New Boyfriend

(And Make Him Fall for You)

Questions to ask a new boyfriend: So, you’ve met a new guy and you’re totally smitten by him. He’s handsome, smart, funny, and charming. You can’t get enough of his texts, calls, and dates. You feel like you’ve hit the jackpot.

But how well do you really know him? Do you know his hopes, dreams, fears, and secrets? Do you know what makes him tick, what turns him on, and what drives him crazy? Do you know if he’s compatible with you, if he shares your values, and if he sees a future with you?

If not, don’t worry. You’re not alone. Many couples fall into the trap of getting too comfortable too soon and skipping the deeper conversations that can strengthen their bond and reveal their true selves.

That’s why we’ve compiled this list of 77 questions to ask your new boyfriend that will help you get to know him better, spark meaningful conversations, and make him fall head over heels for you.

These questions are divided into seven categories: relationship compatibility, about your relationship, about the future, romantic, fun, deep, and cute. You can use them as conversation starters, icebreakers, or date night ideas. You can also mix and match them depending on your mood and the situation.

But before you dive in, here are some tips on how to use these questions effectively:

• Don’t ask them all at once. Choose a few that interest you and go from there. You don’t want to overwhelm him or make him feel like he’s being interrogated.
• Be genuinely curious and attentive. Listen to his answers without judging or interrupting. Ask follow-up questions to show that you care and want to learn more.
• Share your own answers too. Don’t make it a one-sided interview. Open up and reveal something about yourself as well. This will create a mutual trust and intimacy.
• Have fun with it. Don’t take it too seriously or make it a chore. These questions are meant to be enjoyable and playful. Laugh, joke, tease, flirt, and have a good time.

Ready to get started? Here are 77 questions to ask your new boyfriend that will instantly add spice to your relationship.

Relationship compatibility

When you start dating someone new, it can be easy to get lost in chemistry and physical attraction. While both of these things are important parts of being with someone romantically, they are not the only things that matter.

It might feel scary bringing topics up like this with a new boyfriend, but don’t be so afraid of asking the wrong question that you end up wasting time with someone who isn’t compatible.

Here are 10 questions to ask your new boyfriend that will help you assess your relationship compatibility:

1. Are you a night owl or an early bird?
2. Do you like moving around or prefer to be settled in one place?
3. Are you adventurous or more of a homebody?
4. How do you envision your perfect day?
5. Do you see yourself wanting kids one day?
6. How important is self-development to you?
7. How do you deal with stress in your life?
8. How do you express love in a relationship?
9. Would you consider yourself to be a loyal partner?
10. How do you envision splitting finances with your partner?

About your relationship

It’s never a bad idea to check in with your partner to see how both of you are feeling about your relationship and figure out if there are any areas that need extra attention.

By creating an open and ongoing conversation about the ways that you can connect and support each other more deeply, you are much more likely to have a relationship that lasts.

Help build deep intimacy with the following 10 questions:

11. What attracted you to me in the first place?
12. What do you like most about our relationship?
13. What do you think we can improve on as a couple?
14. How do you feel when we’re apart?
15. What are some of the things that make you happy in our relationship?
16. How do you like to be comforted when you’re upset?
17. What are some of the things that annoy you about me?
18. How do you handle conflict in a relationship?
19. What are some of the things that we have in common?
20. What are some of the things that we disagree on?

About the future

One of the most exciting parts of being in a new relationship is dreaming about the future together. Whether it’s planning your next trip, imagining your wedding day, or discussing your career goals, talking about the future can bring you closer and give you something to look forward to.

Of course, you don’t want to rush things or pressure him into making commitments he’s not ready for, but it doesn’t hurt to explore some possibilities and see where he stands on certain topics.

Here are 10 questions to ask your new boyfriend that will help you get a glimpse of his vision for the future:

21. Where do you see yourself in five years?
22. What are some of the things on your bucket list?
23. What are some of the places you want to travel to?
24. What are some of the skills you want to learn or improve on?
25. What are some of the causes you care about or support?
26. How do you feel about marriage?
27. How do you feel about having pets?
28. What are some of the things you want to achieve in your life?
29. How do you balance your personal and professional life?
30. What are some of the things that scare you about the future?

Romantic

Sometimes, you just want to make your new boyfriend swoon with your sweet and romantic questions. Whether it’s complimenting his appearance, expressing your feelings, or asking him to do something special for you, these questions will make him feel loved and appreciated.

You can use these questions to spice up your date nights, surprise him with a text, or whisper them in his ear.

Here are 10 questions to ask your new boyfriend that will make him fall for you even more:

31. What do you think is the most attractive thing about me?
32. How do you feel when I kiss you?
33. What are some of the things that turn you on?
34. What are some of the things that you find romantic?
35. How would you describe our relationship in three words?
36. What are some of the things that I do that make you smile?
37. What are some of the things that you want to do with me?
38. How do you show me that you love me?
39. What are some of the compliments that you like to hear from me?
40. What are some of the things that I can do to make you happy?

Fun

Not every question has to be deep or serious. Sometimes, you just want to have fun with your new boyfriend and laugh until your stomach hurts.

These questions are perfect for breaking the ice, lightening the mood, or playing games. You can also use them to discover his quirky side, his sense of humor, and his preferences.

Here are 10 questions to ask your new boyfriend that will make him laugh and have fun:

41. What is the funniest thing that ever happened to you?
42. What is the most embarrassing thing that ever happened to you?
43. What is the weirdest thing that you’ve ever eaten or tried?
44. What is the craziest thing that you’ve ever done or would like to do?
45. If you could have any superpower, what would it be and why?
46. If you won the lottery, what would be the first thing that you would buy or do?
47. If you could switch bodies with anyone for a day, who would it be and why?
48. If you were stranded on a deserted island, what three things would you want to have with you?
49. If you could travel back in time, what period would you go to and why?
50. If you were a movie character, who would you be and why?

Deep

If you want to take your relationship to a deeper level, you need to ask your new boyfriend some deep questions that will reveal his true self.

These questions will help you understand his personality, his values, his beliefs, and his worldview. They will also challenge him to think critically, reflect on his life, and share his opinions.

You might not agree with everything he says, but that’s okay. The point is to respect each other’s differences and learn from each other’s perspectives.

Here are 10 questions to ask your new boyfriend that will make him think and open up:

51. What makes you happy?
52. When do you feel most fulfilled?
53. How would you define success?
54. Do you consider yourself successful? Why or why not?
55. Do you consider yourself happy? Why or why not?
56. Are you proud of your accomplishments so far? Why or why not?
57. What was your childhood like? Would you change anything about it?
58. How did your parents impact your view on love and relationships?
59. What gets you out of bed in the morning?
60. What is your biggest fear? Do you think you could face it?

Cute

Sometimes, all it takes is a cute question to make your new boyfriend smile and melt his heart.

These questions are sweet, adorable, and innocent. They will show him how much you care about him and how much he means to you.

You can use these questions to brighten up his day, cheer him up when he’s feeling down, or simply express your affection.

Here are 10 questions to ask your new boyfriend that will make him go “aww”:

61. How did you know that you liked me?
62. What is your favorite memory of us so far?
63. What is your favorite thing that I do for you?
64. How do you feel when I hug you?
65. What are some of the nicknames that you have for me?
66. What are some of the things that make you blush?
67. How do you like to be cuddled?
68. What are some of the songs that remind you of me?
69. What are some of the things that you want to say to me but are too shy to say?
70. How do you feel when I say “I love you”?

There you have it, 77 questions to ask your new boyfriend that will help you get to know him better, spark meaningful conversations, and make him fall for you.

You don’t have to ask them all at once or in order. You can pick and choose the ones that suit your mood and situation. You can also come up with your own questions based on your interests and experiences.

The most important thing is to have fun with it and enjoy the process of getting closer to your new boyfriend.

We hope you found this blog post helpful and informative. If you did, please share it with your friends and leave a comment below.

And if you’re looking for more tips and advice on how to have a happy and healthy relationship, check out our other blog posts here.

Thank you for reading and happy dating!