Trying to think of some good conversation starters when talking to your boyfriend? Here are the best deep questions to ask your boyfriend.
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Getting to know each other on a deeper level is one of the most exciting (and sometimes terrifying) parts of a new relationship.
While you’ll never stop learning new things about each other, there are some things that are helpful to know early on in the relationship. You don’t want to be dating for years before you find out that your future plans don’t align.
If you want to know more about your boyfriend’s past life, future goals, political beliefs, etc. you need to know what kinds of questions to ask. That’s why I put together this list of 65 deep questions to ask your boyfriend that will help you get to know him on a more intimate level.
Deep Questions To Ask A Guy About His Past
Your boyfriend obviously had a life before you met him. These questions will help you learn more about his past relationships, family life, and other things that happened before you were a part of the picture.
It’s important to learn about your boyfriend’s past so that you have a strong sense of who he is as a person.
1. Have you ever been in a long term relationship?
2. How long was your longest relationship? Why did it end?
3. Have you ever lived with a partner?
4. What has been the biggest obstacle you’ve faced in life?
5. What is your biggest life regret?
6. How would you describe your relationship with your family?
7. What piece of advice would you give your younger self?
8. Have you ever had your heart broken?
9. Have you ever cheated or been cheated on?
10. Where is your favorite place you’ve traveled?
11. What has been your biggest failure in life? How did you react to it?
12. Have you ever had a long distance relationship? Would you ever be able to do it again?
13. Are you close with your parents? Which one are you closer to?
Deep Questions To Ask Your Boyfriend About The Future
Talking about the future is SO important in any romantic relationship. If you guys don’t have goals that align, it’ll be very difficult to have a future together. These deep questions will help you figure out if you two are compatible for the long term.
14. Do you want to have kids? How many?
15. Where do you want to be in life in 5 years?
16. What kind of impact do you want to leave on the world?
17. Where is your ideal place to live? Would you rather live in the city or the country?
18. If money wasn’t an object, what would you do for a living?
19. How important is it for you to save money?
20. Would you ever want an open relationship?
21. Are there any traditions your family had that you want to continue with your future family?
22. When do you see yourself getting married?
23. What are your career goals?
24. Do you think I would get along well with your family?
25. What’s one thing you hope happens in the future of our relationship?
Cute Deep Questions To Ask Your Boyfriend
Not every deep question has to be super serious. These cute questions to ask him will help you get a better sense of what he’s like as a partner. They’ll also help you figure out what he likes about you and why.
26. What 3 words would you use to describe me?
27. What was the main thing that attracted you to me?
28. How would you describe your ideal partner?
29. What is your perfect date night?
30. When did you first realize you had feelings for me?
31. What is your favorite thing about me?
32. Have you ever been nervous around me?
33. What were your first impressions of me?
34. What is your favorite thing about our relationship?
35. How often did you think about me before we started dating?
36. Would you ever introduce me to your parents?
37. What is your favorite outfit of mine?
Personal Questions To Ask Your Boyfriend
We’ve talked about the past and the future, now let’s hear about who he is right now. Ask him some personal questions so that you get a better sense of his beliefs, fears, personality traits and habits.
38. What is your biggest fear?
39. Do you consider yourself an introvert or extrovert?
40. What are your relationship deal-breakers?
41. Do you have any causes that you feel passionate about?
42. What’s your biggest pet peeve?
43. Do you believe in soulmates?
44. What is the best piece of advice that someone has given you?
45. Do you believe in a higher power?
46. What motivates you?
47. If you could trade places with one person for a day, who would it be?
48. Do you consider yourself more of a planner or are you more spontaneous?
49. Is there anything that offends you?
50. Do you have any habits that you wish you could break?
51. Who are the three most important people in your life?
52. Do you think men should wear the pants in the relationship?
53. What is the last thing that made you cry?
54. If you could fix one problem in the world, what would it be?
“Controversial” Deep Questions To Ask A Guy
As unpleasant as it may seem, it’s so important to know where he stands on the issues that are important to you. Just make sure that you approach these topics respectfully and be ready to change the subject if things get too heated.
55. Are you pro choice or pro life?
56. Did you vote in the last election? Do you still stand by your vote?
57. Would you consider yourself a religious person?
58. Have you ever struggled with any addictions?
59. What’s the most controversial opinion you have?
60. Would you stay with your partner if they were diagnosed with a terminal illness?
61. Is flirting cheating?
62. Could you stay in a relationship with someone who had different political beliefs?
63. Would you ever go through your significant other’s phone?
64. Do you think money can buy happiness?
65. Do you think women should have equal pay to men?
Conversation Starter Games For Couples
Looking for more ways to break the ice? Here are some really fun games to play with your boyfriend that will help you get to know him better.
We’re Not Really Strangers
This card game is SUPER trendy right now and for a good reason.
The game contains 150+ questions to help you deepen your existing relationships, as well as form new ones.
This card game is perfect for couples but it’s also really cool to play with friends and family. The questions on the cards will definitely make you think deeply and help you open up to people in your life.
Couples Conversation Cards
If you’re looking for deep questions to ask your boyfriend or girlfriend, this is the perfect game for you.
It contains over 3000 questions about life, relationships, fears, dreams, etc. that will definitely help you open up to each other.
The cards are color coded so you know what kind of question you’re getting yourself into. Cream colored cards are softball questions, red cards are super deep questions, and the purple cards are *spicy* questions.
If you’re looking for relationship-building conversation starters, you’ll love the Intimacy Deck.
This set contains 150 conversation starters for couples that encourage you to talk about your past, dream about your future, and share some of your deeper truths with each other.
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