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260 Deep Questions to Ask Your Boyfriend

by | Love

Jul 8, 2022

To forge a lasting bond with your boyfriend, a bond closer than that with any other person, you need to know what questions to ask him. Your boyfriend is someone you will probably stick to​—or be stuck with for the rest of your life.

To understand your boyfriend better and learn more about what motivates him and why he behaves in a certain way, you need to ask him these deep questions.

A long-lasting relationship can be a source of rich satisfaction or the opposite. Much depends upon how ready you and your boyfriend are for it. That is why you’re going to find these profound questions very useful. These 260 deep questions will simply make you guys get closer and open up to each other.

Profound Questions to Ask Your Boyfriend

  1. What’s your favorite memory as a child?.
  2. What is your thought on a long-distance relationship?
  3. Which game do you enjoy playing the most?
  4. Do you have any cravings right now?
  5. Have you ever dressed up naked in front of any member of your family before?
  6. What are your expectations in a relationship?
  7. Is there any cliché that motivates you?
  8. Would you cheat on me because of a dare?
  9. Tell me about the day you messed up in high school?
  10. If you just won a lottery for a huge sum of money, what would you do first?
  11. What’s the nastiest thing you ever said?
  12. How do you dodge awkward conversations?
  13. Which superpowers would you love to have?
  14. Would you like a change of name?
  15. What upsets you the most and why?
  16. What music do you play most times on a trip?
  17. What are the things that please you the most?
  18. What’s the most bizarre brand name you can think of?
  19. Do you sometimes talk about a problem if you didn’t want a solution?
  20. Have you ever exchanged your nudes before?
  21. Is there any time you sent your nudes online?
  22. What crime would you have indulged in if not for its consequence?
  23. What project would you like to launch?
  24. Mention one thing you wished you did earlier.
  25. Did you ever beat yourself up for not meeting up?
  26. Have you ever cried publicly before?
  27. Do you make decisions based on your body or mind?
  28. What’s your most pleasant memory?
  29. What mistake has created a scar in your life?
  30. Have you ever felt abandoned before?
  31. What aspirations did you ever let go of?
  32. Which of your achievement are you most proud of?
  33. How do most people see you?
  34. Have you encountered a miracle before?
  35. Have you jilted someone before?
  36. Why would you renege on a promise?
  37. Do you think happiness can be purchased?
  38. Are you ready to have a child soon?
  39. Were you ever been pressured to have sex with someone?
  40. What’s the craziest thing you ever did?
  41. Where’s your favorite place to unwind?
  42. Do you sometimes like to talk dirty?
  43. Which part of a woman’s body drives you wild the most?
  44. When do you feel the most vulnerable?
  45. What is the biggest lesson you’ve learned from previous relationships?
  46. How much do you trust me?
  47. What qualities are you looking for in a life partner?
  48. Have you done online dating before?
  49. Where do you find relief after meeting when having a bad day?
  50. What’s one thing you can never get tired of?
  51. Is cohabitation ideal for us?
  52. What do you think of me?
  53. How often should we keep in touch?
  54. Which top 3 ladies would you like to hang out with?
  55. How long can you stay without sex?
  56. Would you ever believe someone else that told you I am cheating on you?
  57. What’s your favorite cologne?
  58. When did you start thinking of being with me?
  59. Do you believe in love at first sight?
  60. Have you ever dreamt of me?
  61. What arouses you the most?
  62. Can you envision having kids in the future?
  63. What color of lingerie would you like me to try on?
  64. What’s the nastiest thing on your bucket list?
  65. Have you ever faked an orgasm?
  66. How do want our income to be budgeted?
  67. How much money can one of us spend on buying something without consulting the other?
  68. Which music artist is your favorite?
  69. Is your libido high?
  70. Do you secretly look lustfully at other women?
  71. What is your worst subject in school days?
  72. Which is your favorite music?
  73. Do you like any author?
  74. Who did you have your most serious conversation ever with?
  75. Which fancy restaurant would you love to eat in?
  76. Are you taking the meals or the drink first at a table?
  77. How do you handle conflict in your past relationships?
  78. Coffee or tea?
  79. Did you ever at one point get so drunk that someone took you home?
  80. Which of your boss would you like to work with?
  81. Do you like your neighbors?
  82. Are you an alpha male?
  83. Have you ever gone to bed hungry?
  84. What’s your perfect date like?
  85. Do you think true love exists?
  86. What would be our love song?
  87. Do you prefer kissing to hugging?
  88. Is our level of honesty enough for this relationship?
  89. Do you think I am right for you?
  90. Is there any ex you would like to reconcile with?
  91. Would you like to have an intimate wedding?
  92. Are you a romantic person?
  93. How long can you ignore me after a fight?
  94. Do you fancy long-distance relationships?
  95. What new things have you learned from me?
  96. Do you get nervous in public?
  97. What scares you the most?
  98. Is there any heritable illness in your family line?
  99. Is your family gender-biased?
  100. What was your thought about me when we first met?
  101. Have you had a habit of viewing pornography?
  102. Are you a party animal?
  103. Do you give to the needy?
  104. Can you forgive and forget?
  105. Between your bestie and girlfriend, if you were to save just one person, who would it
  106. Would you ever pursue fame?
  107. Would you take a bullet for your mother?
  108. When was the last time you were encouraged?
  109. Which childhood tradition do you cherish?
  110. What would you like to see now that would happen in the future?
  111. Did you like our first kiss and why?
  112. How do you cope with the aftermath of your last breakup?
  113. Would you love to make out in the water?
  114. Will you tell me tales by the moonlight?
  115. Are you nocturnal?
  116. What’s the most thoughtful thing you ever did for a partner?
  117. Do you still get butterflies in your tummy when you see me?
  118. What do you value most in a relationship?
  119. What was a betrayal like to you?
  120. When do you get overwhelmed?
  121. What is not true about you on your CV?
  122. What is your most valued possession?
  123. Which celebrity are you crushing on?
  124. What public holiday is your favorite?
  125. Are you closer to your mom or dad?
  126. Would you serve a girl breakfast in bed?
  127. What is your soft spot?
  128. How do you relate with people of a lower social class?
  129. What trait would you work on now to help improve our relationship?
  130. Where do you see yourself 20 years from now?
  131. Have you ever made a life-changing decision?
  132. What would you like to change about yourself?
  133. Which social media platform are you most active on?
  134. Do you feel threatened by a woman who is doing well financially better than you?
  135. Have you ever been in a friend with benefits situation before?
  136. What effort have you made in the past that really paid off?
  137. Which famous person do you think has good leadership skills?
  138. Who has ever left a great imprint on your heart?
  139. Which state would you like to relocate to after retirement?
  140. What compliment have you received that you can never forget?
  141. Which cooking ingredient or spice are you allergic to?
  142. Are you a virtuoso?
  143. When was the last time you felt accomplished?
  144. How many foreign languages do you speak?
  145. What news headline is catchy to you?
  146. Have you ever gotten lost in a new environment before?
  147. What would you advise everyone to do?
  148. How often do you procrastinate?
  149. What one wish would you like to make?
  150. Do you get provoked easily?
  151. Do you feel exhausted or energized after hanging out with people?
  152. What are your boundaries?
  153. Would you prefer to be respected or to be loved?
  154. What do you think of karma?
  155. Do you want to do twosome?
  156. What’s your signature dance step?
  157. What’s your genotype?
  158. Can you lie to protect someone from being killed?
  159. Which event are you waiting to experience soon?
  160. Do you have any pets?
  161. Have you ever cheated in an examination before?
  162. Do you have suicidal thoughts?
  163. Diamond or gold, which would you have?
  164. Where is your honeymoon destination?
  165. What substance did you abuse the most as a teenager?
  166. Would you like to further your education?
  167. How about a career change?
  168. Would you want to remain forever young?
  169. Does the idea of growing old frighten you?
  170. Have you ever doubted your feelings for me?
  171. What caught your attention the first time you stepped into a home?
  172. Where do you do your shopping?
  173. How vital are honest and open communications to you and why?
  174. Does flirt appeal to you?
  175. Do you have any daily rituals?
  176. What’s the name of the biggest scammer you ever met?
  177. Are you a social butterfly?
  178. How often do you shave?
  179. Any blind dates so far?
  180. Which famous person would you have loved to still be alive?
  181. Have you ever dated an older woman?
  182. If I relocate, would you come along with me?
  183. What is something most people appreciate you for?
  184. Why did you end your last relationship?
  185. How can I support your passion?
  186. Do you live alone?
  187. Have I belittled you in any way?
  188. Is there anything else I should know about you?
  189. What are your expectations for this relationship?
  190. Do you think monogamy is for you?
  191. What differentiates me from other women?
  192. Would you share a room with a snorer?
  193. What best decision of your life would you like to make again?
  194. Do you think you are living up to your potential?
  195. Who would take the major decision in our relationship?
  196. Do you owe any debt? If so, what steps are you taking to pay off the debt?​
  197. What makes you sad?
  198. How do you cope with challenges?
  199. What is your body count?
  200. How regular do you go for STI testing?
  201. Do you have a nickname?
  202. When would you like to settle down?
  203. Do you like public displays of affection?
  204. What was growing up in your family like?
  205. Do you like surprises?
  206. How would you react to your friends flirting with me?
  207. Are you seeing someone else?
  208. What are we?
  209. How do you handle rejection?
  210. What terrible experience did you have that became a blessing in disguise for you?
  211. Which couple do you admire?
  212. Describe your dream home?
  213. Do you love to be pampered when sick?
  214. What’s the worst gift you ever got?
  215. Are you secretive?
  216. What song would you like to dedicate to me?
  217. Do you go clubbing till daybreak?
  218. How diplomatic are you?
  219. What is your skill set?
  220. Do you sometimes talk to yourself?
  221. Are you a jealous person?
  222. What would you like to be remembered for?
  223. What is your family dynamic?
  224. Describe your spending habits
  225. What are the 5 things you can’t do without in a week?
  226. What’s your football club?
  227. How can I make you feel loved today?
  228. Mention what you can never compromise on?
  229. Do you find our love life satisfying?
  230. Which of my qualities attracted you to me?
  231. Have I changed?
  232. What’s one thing you will never do again?
  233. In what area is our relationship lacking?
  234. What’s the bravest thing you have ever done?
  235. Were you ever engaged or married?
  236. Have you been in an abusive relationship before?
  237. Is spirituality or religion important to you?
  238. What was your longest relationship duration?
  239. Are you mentoring anyone?
  240. Do you like your current job?
  241. Any major turning point in your life so far?
  242. What are you desperate to get now?
  243. Describe yourself in 3 words.
  244. Have you lost any loved ones?
  245. Would you go for looks or character in a person?
  246. At what age did you have your first sex?
  247. Are you a single father?
  248. Do you still watch cartoons?
  249. What’s freaking you at the moment?
  250. Is there something else that is important you think I should know about you?
  251. Have you ever had a casual relationship?
  252. Have you ever had sex in a car?
  253. Have you loved someone who doesn’t reciprocate your love?
  254. Have you fought for a girl you love at any point in your life?
  255. Do you ever dread losing me?
  256. How well do you manage money?
  257. What will your family expect of us?
  258. Have you ever dated someone simply to satisfy your sexual desires?
  259. What kind of fun do you want to get out of life?
  260. To what extent are you prepared to take on the role of a long-lasting relationship?

Related: Deep Questions to Ask Your Girlfriend

Bottom Line

To strengthen your bond and relationship with your boyfriend, ask him these deep questions while you communicate with each other. Respond humbly to the answers he gives you. And as you discuss these deep questions together, assure him of your love through your words and actions. He will come to appreciate and love you even more.

Photo by Andres Ayrtonon Pexels.

By Rachael Ukpebor

Rachael Ukpebor is an Editorial Assistant for Whatsdalatest. She graduated with honours from the University of Benin with a degree in Sociology and Anthropology. She covers beauty, relationship, and lifestyle topics at WDS, everything from best skincare and makeup hacks, to relationships. Her favourite music is Lovin' You by Minnie Riperton.

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