How Well Do You Know Me Questions To Challenge Your Partner

What are some good questions to test how well you know someone?
on August 22, 2023
Read time: 10 mins

Have you ever looked at your partner and thought, ‘how well do you really know me?’

If so, these how well do you know me questions are right up your street! As we know, building a relationship is all about getting to know your partner on a deeper level in order to enhance your connection and strengthen your bond. 

With a mix of deep questions, romantic inquiries, and wacky facts, these questions are a fun way to test your knowledge of your partner and see just how well they really know you. 

What are the best questions to ask when you’re playing the couple's game? 

When embarking on this fun quiz game, it’s important to consider the kind of questions you will be asking! 

Throughout relationships, every couple leaves hints about various aspects of their lives, and may even tell in-depth stories about their past — but how much does your partner remember? 

Depending on how long you know each other, even if your partner doesn’t know the answer, it’s a fun opportunity to delve into the past and reveal more about yourself. So don’t be too offended if they don’t get the highest score, consider it as a learning curve!

250 how well do you know me questions to ask your partner 

Right, it’s time to get down to business! 

Brush up on your facts and learn more about your significant other with these carefully-curated questions, featuring everything from favorites to fantasies. If you want to turn it into a variation of the Newlywed Game (no matter your marital status), make sure you keep score! 

  1. Who is my best friend and how long have we known each other? 

  2. Do I believe in zodiacs and star signs? 

  3. What is my biggest regret? 

  4. Do I have any birthmarks? If so, what are they? 

  5. Am I more of a morning person or a night owl? 

  6. If I could eat one food for the rest of my life, what would it be? 

  7. Who is my greatest role model? 

  8. Do I support any sports team? 

  9. How did I meet my best friend? 

  10. What is my worst dating faux pas? 

  11. Which friend would I drop everything to go and help if they asked me? 

  12. What was my first job? Was I any good at it? 

  13. Tell me the details of my first kiss. Or do you know what age I was? 

  14. What is my go-to icebreaker for work calls or social events? 

  15. Did I have an imaginary friend? What was their name? 

  16. Am I more of an introvert or an extrovert? 

  17. What is my go-to karaoke song? 

  18. Growing up, who was my closest friend? 

  19. If I could bring one loved one back to life one day, who would I choose? 

  20. What is my most embarrassing moment? 

  21. What personal questions do I always shy away from? 

  22. If I could have any superpower, what would it be? 

  23. What video games did I love as a child? 

  24. What is the worst date I have ever been on? 

  25. What is my zodiac sign? 

  26. How many best friends do I have? 

  27. Am I a dog or cat person? 

  28. What’s my favorite childhood memory? 

  29. What are my go-to conversation starters in an awkward situation?

  30. Who’s my secret celebrity crush? And is it different from the crush I tell people about? 

  31. What is my favorite place to go for our date night? 

  32. What family member am I closest to? 

  33. Who is the one celebrity that I would love to be best friends with? 

  34. What’s my most prized possession? 

  35. What’s my favorite tv show? 

  36. Which friend would I ask to be my maid of honor/best man at our wedding? 

  37. Do I have a favorite sport? Am I any good at playing it myself? 

  38. What was my favorite part of our first date?

  39. Which of my friends is the biggest gossip? 

  40. What was my senior prank in high school? 

  41. Who is my favorite actor or actress? 

  42. Did I like you straight away on our first date, or was I more of a slow burner? 

  43. What was my favorite subject in high school? 

  44. Am I allergic to anything? 

  45. What is my favorite thing about you? Both personality and physical features! 

  46. During high school, how many relationships did I have? 

  47. What is the last book that I read? 

  48. What is my favorite movie? 

  49. What are your biggest insecurities? 

  50. Have I ever lived with a significant other before? 

  51. What is my biggest pet peeve? 

  52. Did I have a high school crush? 

  53. What’s my least favorite season of the year? 

  54. Describe my dream date night, with no budget or limits! 

  55. What is my favorite book? 

  56. Do I have any icks? If so, what are they? 

  57. Which family member did I always squabble with as a child? 

  58. Do I have a favorite band? 

  59. What was the first band or artist I ever went to see live? 

  60. What is my current favorite song? 

  61. Did I play any sports in high school? If so which ones? 

  62. Who was my favorite teacher in school? 

  63. What is my favorite food? 

  64. Describe my ideal weekend - no details spared! 

  65. Which subject was my least favorite in high school? 

  66. What’s my least favorite chore to do around the house? 

  67. What is my comfort book to re-read over and over? 

  68. What’s my least favorite airport to travel from & why? 

  69. Can you name everything on my bucket list? 

  70. What’s my favorite season of the year? 

  71. Do I prefer ice cream or frozen yogurt? 

  72. What’s my favorite season to dress for? 

  73. What is my favorite color? 

  74. What’s my favorite thing about our family? 

  75. What is my favorite fancy restaurant for a special occasion? 

  76. When was the last time I got out of my comfort zone? 

  77. Would you rather have sprinkles or syrup on my ice cream? 

  78. What was my favorite tv show as a child? 

  79. When was the last time I cried over something silly? 

  80. What’s my favorite flavor of ice cream? 

  81. What is my favorite song to sing in the shower? 

  82. What is my favorite restaurant for comfort food? 

  83. What's my favorite way to spend a Sunday afternoon?

  84. Do I prefer coffee or tea in the morning?

  85. Am I afraid of heights or spiders?

  86. What's my dream travel destination?

  87. What's my go-to workout song?

  88. Do I prefer solo travel or group trips?

  89. How do we like to celebrate anniversaries?

  90. What's my favorite kind of weather?

  91. Which city or country do I dream of visiting one day?

  92. What's my favorite genre of music?

  93. What's my favorite piece of technology that I own?

  94. Do I prefer sweet or savory breakfasts?

  95. How do I feel about lending money to friends or family?

  96. How do I typically handle stress or frustration?

  97. What's my preferred method of communication: text, call, or face-to-face?

  98. How do I feel about meeting new people?

  99. What qualities do I value most in friends?

  100. What's the story behind how we first met?

  101. How do I typically celebrate my birthday?

  102. What's my biggest fear?

  103. What's a goal I'm currently working towards?

  104. Who in my family do I talk to most frequently?

  105. What's my favorite way to spend time with you?

  106. What was the name of my first pet?

  107. Can you describe my childhood home?

  108. How do I feel about social media and online connections?

  109. What's my philosophy on money and finances?

  110. What's my favorite type of coffee?

  111. Do I prefer mountains or beaches for vacation?

  112. What was the name of my elementary school?

  113. What was my first car, and do I have any fond memories of it?

  114. Did I ever get into trouble as a child? What for?

  115. Who was my teenage celebrity crush?

  116. What's my favorite animal, and why?

  117. What's my ideal way to relax after a hard day?

  118. Do I prefer wearing jeans or dresses/suits?

  119. What do I find most attractive about you?

  120. What's our song?

  121. What's my favorite hobby or pastime?

  122. Do I enjoy cooking, and what's my best dish?

  123. What's my favorite outdoor activity?

  124. What do I like most about my current job?

  125. What was my dream job as a child?

  126. How do I usually handle work-related stress?

  127. What's something I'd like to learn or achieve in the next year?

  128. How do I usually express love or affection?

  129. What's my view on marriage and long-term commitments?

  130. What's the most courageous thing I've ever done?

  131. What's my favorite piece of art or creative expression?

  132. How do I feel about aging and growing older?

  133. What's my favorite video game or mobile game?

  134. What's my favorite way to spend a rainy day?

  135. Do I enjoy going to live concerts or theater shows?

  136. What's my favorite magazine or online publication?

  137. What's my favorite type of exercise or workout?

  138. What's the most meaningful compliment I've ever received?

  139. What's the one thing about myself that I'm most proud of?

  140. What's the biggest challenge I've faced in my career?

  141. How do I handle grief or loss?

  142. What's the most meaningful gift I've ever given?

  143. What's my attitude toward education and lifelong learning?

  144. How do I usually approach resolving conflicts with friends or loved ones?

  145. What's the biggest risk I've ever taken?

  146. What's my most cherished keepsake or memento?

  147. How do I feel about environmental issues and sustainability?

  148. Who has been my mentor or biggest influence professionally?

  149. Do I prefer museums or outdoor parks?

  150. What was my impression of your family the first time I met them?

  151. What's my favorite brand of chocolate?

  152. What's my signature dance move?

  153. What makes me feel most fulfilled?

  154. What's my favorite form of artistic expression?

  155. Do I prefer city life or country living?

  156. What's my favorite way to surprise you?

  157. How do I feel about participating in team sports or group activities?

  158. What's the most thoughtful gift I've ever given to someone, and why?

  159. How would my friends describe me?

  160. What family traditions do I cherish most?

  161. What's my favorite memory of my siblings?

  162. How do I usually celebrate my friends' successes?

  163. Who was my childhood hero or role model?

  164. How do I feel about public displays of affection?

  165. What's the most memorable trip we've taken together?

  166. How would I describe our first kiss?

  167. What do I love most about our relationship?

  168. How do I feel about politics and current events?

  169. What's the most romantic thing I've done for you?

  170. If I could have dinner with any three people from history, who would I choose?

  171. What's my philosophy on work-life balance, and how do I try to achieve it?

  172. How do I like my eggs cooked for breakfast?

  173. What's my favorite board game or card game?

  174. What's the last hobby I picked up?

  175. What's my go-to snack at the movies?

  176. How do I feel about roller coasters?

  177. What's my favorite type of puzzle or brain teaser?

  178. Do I have a favorite quote or saying?

  179. What's the most unusual job I've ever had?

  180. How do I feel about fame and public recognition?

  181. What's the most important lesson I want to pass on to future generations?

  182. What's the legacy I hope to leave behind?

  183. What's my favorite ethnic cuisine?

  184. How do I like my steak cooked?

  185. What's my biggest financial goal?

  186. How do I usually handle money in our relationship?

  187. What's the most meaningful song or piece of music in my life?

  188. How do I feel about technological advancements and modern innovations?

  189. What's my favorite way to spend a long weekend or vacation?

  190. How do I feel about personal appearance and grooming?

  191. What's the most extravagant thing I've ever bought?

  192. What's my attitude toward savings and investments?

  193. What's the most beautiful place I've ever visited?

  194. What's my favorite way to show you that I love you?

  195. What's my favorite type of weather, and why?

  196. Do I have any unusual eating habits?

  197. What's my favorite cocktail or non-alcoholic beverage?

  198. How do I feel about long-term commitment and plans for the future?

  199. What's my favorite home-cooked meal?

  200. How do I feel about public speaking or performing in front of others?

  201. What's a romantic tradition we have?

  202. What's my go-to way to unwind and de-stress?

  203. What's my favorite type of workout or physical activity?

  204. How do I usually cope with illness or feeling under the weather?

  205. What's my favorite form of self-care or pampering?

  206. What's my zaniest or most irrational fear?

  207. What's a subject I could talk about for hours?

  208. What's my favorite way to spend time outdoors?

  209. What's my favorite guilty pleasure TV show or movie?

  210. What's the most adventurous thing I've ever done?

  211. Have I ever met anyone famous, and what was that like?

  212. What's the most meaningful gift I've ever received?

  213. What's the best way to cheer me up after a tough day?

  214. What's our most memorable romantic getaway?

  215. What's a cherished family heirloom?

  216. What's my favorite family vacation memory?

  217. What's the strangest experience I've ever had?

  218. What's my preferred way to spend a snow day?

  219. What's a cause I'm really passionate about?

  220. How do I feel about pineapple on pizza?

  221. Do I have any odd or unusual talents?

  222. What hobbies have I always wanted to pick up but never did?

  223. What's my favorite way to volunteer or give back to the community?

  224. Do I prefer baths or showers?

  225. What's my stance on ethical consumption?

  226. What's a family recipe that I love?

  227. What's my favorite motivational quote or mantra?

  228. What's my go-to comfort movie or TV show?

  229. How do I feel about tattoos and piercings?

  230. What's the most challenging decision I've ever had to make?

  231. How do I feel about political engagement and activism?

  232. What's my favorite childhood toy or game?

  233. What's my dream car or mode of transportation?

  234. What's my favorite way to connect with nature?

  235. What's the most meaningful act of kindness I've ever received?

  236. How do I feel about traditional gender roles and expectations?

  237. What's my favorite historical period or cultural era?

  238. What's my favorite way to celebrate New Year's Eve?

  239. What's the most difficult obstacle I've overcome?

  240. What's the most difficult lesson I've learned in life?

  241. What's my favorite type of personal or professional development activity?

  242. How do I feel about friendships and maintaining social connections?

  243. What's my favorite way to honor or remember loved ones who have passed?

  244. How do I feel about aging and the passage of time?

  245. What's my favorite holiday and how do I like to celebrate it?

  246. What's the most rewarding part of my current job or career?

  247. How do I feel about medical or health-related issues?

  248. How do I feel about pets and animal companionship?

  249. What’s my favorite podcast to listen to during my commute? 

  250. What's my preferred way to celebrate personal achievements?

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