213 Insightful Questions To Get To Know Your Boyfriend Better Tonight

Are you in a committed relationship with a guy that feels like it might be #endgame for you? You like each other a lot, so far, he’s been saying and doing all the right things, and you can see a real future with this man. But you want to know more… about his past, quirks, values, fears, and dreams—and you’re right to want to learn more. You need to see if you align with the big things, what makes this guy tick, and be aware of potential relationship pitfalls. So, if you want to get to know your boyfriend better, you need to know the right questions to ask to get to know him on a deeper level.

Men have a terrible reputation for being closed books and unwilling to express their emotions. If you’re dating a man who doesn’t often open up to you and gives you plenty of one-word answers, these questions should help you open him up a little and steer the conversation in the right direction. It’s important to remember that every man is different, and every relationship is different. Some of these questions will be a goldmine, and others may fall flat—so don’t give up if they do.

You might want to set aside a few hours and have a “get to know you better” marathon where you take turns to ask each other some of the questions on this list. Alternatively, you could slip one or two questions into your everyday conversations and keep things a little more low-key. The choice is yours.

213 of the best questions to get to know your boyfriend better

Fun questions to get to know your boyfriend

1. What vacation would you most like to go on with me?

2. What hobby or skill would you be excited to learn together?

3. If you won the lottery, how would you spend the money?

4. My biggest dream is to (fill in the blank)—what do you think about it?

5. What is your dream job?

6. When was the last time you voted?

7. What’s on your bucket list?

8. What makes you happy to be alive?

9. What quirks does your body have?

10. If your entire life was a book, what would the title be?

11. What website doesn’t exist, but you think it should?

12. If you could go on a road trip right now, where would you go?

13. What animal do you think you could wrestle with and win?

14. How do you feel about taking a hot air balloon ride with me?

15. What is the most cringey thing do you do regularly?

16. Have you ever played a game and let someone else win?

17. At the beach, would you prefer to sunbathe with me or dive straight into the water?

18. When did you last laugh so hard it hurt?

19. What’s the craziest thing you’ve ever done?

20. When you were little, who did you want to be when you grew up?

21. What was the last book you read and loved, and why?

22. What is the best gift you’ve ever received?

23. If you could switch places and be a woman for a day, would you? If so, what would you do?

24. What is your idea of a perfect day?

25. You’re in an amusement park—which ride do you go on first?

26. What is your ultimate favorite thing to do on a rainy day?

27. If aliens invaded Earth, what do you think they would look like?

28. What do you think people most need to calm down about?

29. What toy did you always ask for as a child but never got?

30. When was the last time you went into a room and forgot why? Does this happen often?!

31. What’s the most hilarious thing someone has drunkenly confessed to you?

32. Italian or Japanese? Coffee or tea? Cat or dog? Dinner or dessert? Beach or mountain?

33. What’s the grossest thing you’ve ever eaten or drunk?

34. If you could only wear one outfit for the rest of your life, what would it be?

35. What is your favorite city in the world?

36. Do you think animals can understand us?

37. You’re on death row and have to choose your final meal—what would it be?

Romantic questions to get to know your boyfriend

38. When you first saw me, what did you think?

39. When do you feel most appreciated by me?

40. Do you believe that everything happens for a reason? If so, why do you think we met?

41. What one thing instantly makes a woman more attractive to you that is not appearance-related?

42. What’s the best date you’ve ever taken someone on or been taken on?

43. If you had to plan the perfect date to take me on, where would we go?

44. Who was your first crush?

45. What was your first kiss like?

46. Have you ever kissed someone under mistletoe?

47. How would you describe our first kiss?

48. What is your favorite part about dating?

49. What do you think of PDAs (public displays of affection)?

50. When did you first know you liked or loved me?

51. When and how did you know you wanted to be exclusive with me?

52. Do you believe in soulmates?

53. Do you remember the day we met?

54. How many times did you fantasize about kissing me before our first kiss?

55. How did you know you were ready to say “I love you” to me for the first time?

56. Is there a song that comes on the radio that always makes you think of me?

57. What’s more romantic: kissing in the rain or kissing under the moonlight?

58. If we got married, where would you want to go on honeymoon?

59. On a scale of 1 to 10, how much do you like to snuggle?

60. When you wake up next to me, what do you think of first?

Flirty questions to ask your boyfriend

61. If I gave you a massage, where would you like me to pay extra special attention?

62. When was the last time you had a sexy dream about me?

63. When you’re alone in bed, do you ever think about me?

64. How do you feel about pet names?

65. Have you ever gone skinny dipping?

66. What was the most recent thing I did that made you blush?

67. What words or phrases turn you on the most?

68. Do you have a celebrity crush?

69. What is the sexiest thing you’ve seen me wear?

70. What are your most sensitive places to be touched that don’t always get much attention?

71. Have you ever played “I’ve never?” What’s the most embarrassing sexual thing you admitted to doing?

72. What do you think your most attractive physical feature is?

73. What are your favorite scents?

74. Physically, what is the first thing about me that caught your eye?

75. What would I be surprised to find in your bedroom?

76. Where on my body is your favorite place to kiss me?

77. What do I do that turns you on the most?

78. How often do you like to have sex per week to feel satisfied when you’re in a relationship?

79. What is your biggest sexual fantasy?

80. Where has been the most unexpected and enjoyable place you’ve ever had sex?

81. What or who would you love to see me dress up as in the bedroom?

82. What is the most out-there thing that turns you on?

83. How do you feel about porn?

84. What is your all-time favorite sexual position?

85. What is your least favorite sexual position?

86. Has anyone ever walked in on you in the middle of sex? What did you do?!

87. What is the wildest thing someone has asked to do in bed? Did you do it?

Intimate questions to get to know your boyfriend

88. On a scale of 1 to 10, how easy is it for you to talk about your feelings?

89. When was the last time you cried? What made you cry?

90. Do you think you have a “type” when it comes to the women you’re attracted to?

91. What is one thing you wish I would compliment you more on?

92. At what age did you have your first kiss?

93. When was the first time you masturbated?

94. Have you ever been in love before?

95. Have you ever had your heart broken?

96. What do you love most about being in a relationship?

97. When do you feel closest to me?

98. What would you define as cheating?

99. How old were you when you first had sex?

100. How did you lose your virginity?

101. Do you think we have a physical and emotional connection?

102. Have you ever been in an abusive relationship?

103. When was the last time you felt taken care of?

104. Do you think we have enough sex?

105. How many sexual partners have you had?

106. When was the last time you got tested for STDs/HIV?

107. Have you ever had an open relationship?

108. What is your favorite part about sex?

Deep questions to get to know your boyfriend

109. Is there anything you want to tell me but haven’t found the courage to?

110. What do you think is the best thing about being in a relationship with you?

111. How did your last relationship end?

112. Are you friends with any of your exes?

113. What was the most challenging period of your life so far?

114. Do you get stressed much? How do you cope with stress?

115. What is the most significant risk you’ve taken in your life?

116. Apart from cheating, what would make you end a relationship?

117. What’s the worst thing you’ve ever done in a relationship?

118. Have you ever spent the night in jail?

119. What’s the worst breakup you’ve ever experienced? Why was it so bad?

120. Would you say you’re a religious or spiritual person?

121. How do you feel about gay rights?

122. Would you say you’re a feminist?

123. Do you think money can buy happiness?

124. What is the number one thing you want to achieve in your life?

125. Have you ever been to therapy?

126. What accomplishment are you most proud of?

127. When did you give something your all (like everything you had), but it still wasn’t enough?

128. What are your biggest fears?

129. Do you have a good relationship with your family?

130. Are you an introvert or an extrovert?

131. Is there anything you want to change about yourself?

132. What do most people overestimate about you?

133. What do most people underestimate about you?

134. Do you hold grudges?

135. Have you ever struggled with addiction?

136. Do you think it’s ever okay to lie?

137. What about you scares you the most?

138. Do you know your love language?

139. If you could change one thing about your life, what would it be?

140. What’s the most awful nightmare you’ve ever had?

141. What do you get overly emotional about?

142. What percentage of the bad stuff that happens in your life is on you?

143. When are you the most yourself?

144. Do you have any regrets?

145. What are you overly hard on yourself for, and why do you think that is?

146. What makes you different from most people?

147. When you’re having a bad day, what can I do that would make you feel a little better?

148. When was the last time you cried?

149. What is the hardest decision you’ve ever had to make?

Relationship questions to get to know your boyfriend

150. Are you comfortable talking about the future of our relationship?

151. What do you love most about our relationship?

152. How can we support each other more?

153. What does a typical day of a couple with a healthy relationship look like?

154. Are we changing each other in positive ways?

155. What’s your most significant rule in a relationship?

156. What one change can I make that would make our relationship better?

157. When we’re not together, do we communicate enough?

158. Do you think we fight fair?

159. What is the number one quality you usually look for in a partner?

160. Have you ever snooped on a partner (looked at their phone, checked their internet history, followed them somewhere)?

161. What’s the best relationship advice you’ve ever received?

162. Do we spend enough time together?

163. What do you think a wife’s role is in a relationship?

164. What do you think a husband’s role is in a relationship?

165. Are we enabling each other’s bad habits?

166. Where do you get your beliefs about what a good relationship looks like?

167. What’s the best thing about being in a long-term relationship?

168. What’s the worst thing about being in a long-term relationship?

169. Who in your life do you think has the healthiest relationship with their partner?

170. What is your all-time favorite memory from our relationship so far?

171. Do you ever boil over with anger? If so, how often, and what does it look like?

172. How do you usually handle disagreements in a relationship?

173. What could you do that might make me question your loyalty?

174. Do you think it’s okay for people to vent to others about their relationship issues, or do you think that should be kept within the walls of the relationship?

175. When you break up with someone, how do you usually do it?

176. If I were offered a promotion and had to move far away, would you move with me?

177. Where do you see our relationship in five years?

178. How long was your longest relationship?

179. Why did your last relationship end?

180. What do you think helps keep a relationship strong over time?

181. Have you ever lived with a partner?

182. Do you think you can save a relationship after someone cheats?

183. Have you ever cheated on anyone?

184. Have you ever been cheated on?

185. Is there anything you wish I understood about you more?

186. How do you think we can listen better to each other?

Serious questions to ask your boyfriend about the future

187. Do you ever want to get married?

188. Do you want to have children someday? If so, how many?

189. Have you ever gotten anyone unintentionally pregnant? How did you handle it?

190. What do you fear most about the future?

191. What does love mean to you?

192. If your friends told you to break up with me, how would you react?

193. What does being in a committed relationship with someone mean to you?

194. How much work should a couple put into having a successful relationship?

195. What do you want out of our relationship?

196. How would you feel if I met your parents and they didn’t like me?

197. Why do you think our relationship works?

198. What does your ideal Sunday with me look like?

199. Have you ever broken the law?

200. What do you want to do when you retire?

201. Where do you see yourself living long-term?

202. How serious should it get before a married couple sees a coach, counselor or therapist?

203. What are your dealbreakers in a relationship?

204. What’s one thing you’re looking forward to about getting old?

205. Do you think your family and friends will like me when we finally meet?

206. How would you describe your relationship with money?

207. How would you cope if you lost your job?

208. What about if I lost my job?

209. Have you ever been engaged or married?

210. What are your thoughts on marriage?

211. What are your thoughts on divorce?

212. Does it feel like we act as a team?

213. If you could change one thing about us as a couple, what would it be?

Conclusion

I guarantee these questions will help you get to know your boyfriend on a deeper level, build emotional attraction, and help you figure out whether this is the right relationship for you.

Are you ready to try them out?

I’d love to know what are some of your go-to questions when trying to get to know a boyfriend better? Tell me all in the comments below.