150 Questions You Need to Ask Your Long-Term Boyfriend

Hate Date - Reductress

You’ve made the commitment and put in the time—you’re officially in it with your beau for the long haul. By now you know communication is the key to any successful relationship, so to avoid any surprises or disappointments, here are 150 questions you should ask your boyfriend RIGHT NOW:



  1. Where do you see us in five years?
  2. What do you think about children?
  3. What’s one thing you wish you could change about our relationship?
  4. Do you think we should go to Kara’s birthday thing on Saturday?
  5. Have you seen my keys?
  6. Have you traveled to Africa in the last 21 days?
  7. Why don’t you wear that grey sweater more often?
  8. What’s your #1 sexual fantasy?
  9. Okay, nope, what’s your #2 sexual fantasy?
  10. Do you think cell phones are going to give everyone brain cancer?
  11. Do you like my hair wavy, straight, or in a ponytail?
  12. Sparing no details, what is your family health history?
  13. Beatles or Rolling Stones?
  14. Why don’t you just write things down and that way you won’t forget?
  15. Are we free this Saturday?
  16. Does your Gmail on your phone ever do that thing where it displays only one letter per line for the entire email?
  17. Do you want the rest of this?
  18. Have you ever cheated?
  19. Have you ever seen Gilmore Girls?
  20. How many times do you think you’ve had sex?
  21. What’s black and white and red all over?
  22. Will you please apologize to my sister?
  23. What time do you think we should leave?
  24. Can you pick up ice cream on your way over?
  25. Are you asleep?
  26. Why are you getting defensive?
  27. Can I borrow your phone charger?
  28. Have I ever told you about my friend Danielle?
  29. Why don’t we go on dates anymore?
  30. Would you still love me if I got in a horrible accident that left me covered in scars?
  31. Did you see what Emily posted on Facebook?
  32. Are you ready for bed?
  33. What’s your ETA?
  35. Can you even believe it?
  36. What’s your favorite color?
  37. Do you remember how to do a capital Q in cursive?
  38. Is Heaven “for real”?
  39. Have you ever measured your dick?
  40. How recently did you measure your dick?
  41. Did you measure it flaccid or erect?
  42. WAIT HOLD ON do we have a ruler or a measuring tape or something?
  43. What’s your favorite Fleetwood Mac album?
  44. Should America switch over to the metric system?
  45. Are you mad at me?
  46. Do you believe in soulmates?
  47. Can we take a cab if I pay for it?
  48. How’s your family doing?
  49. Huh?
  50. Do you think it’s my fault?
  51. What do you want to do for your birthday this year?
  52. Do you like surprises?
  53. Do you like Haim?
  54. What do you want to watch?
  55. Did you see that dog????
  56. Did you get my text?
  57. Did you get my email?
  58. Did you get my Gchat?
  59. Did you get my call?
  60. Did you get my message?
  61. How do zippers actually work?
  62. How was your day?
  63. What’s your favorite font?
  64. How many licks does it take to get to the center of a Tootsie Pop?
  65. How are you?
  66. Do you remember our first date?
  67. Do you vote in every election?
  68. Wanna maybe see a movie this weekend?
  69. Who are you texting?
  70. Would you still go down on me even if you were to hypothetically sustain a terrible jaw injury?
  71. Would you still go down on me if I got into a terrible accident and was covered in scars?
  72. Are you sure you’re not mad at me?
  73. Can I see your phone for a sec?
  74. Did you bring the tickets?
  75. What were you thinking?!
  76. Can you tell my right boob is bigger than my left?
  77. Do you remember that stripey scarf I used to wear all the time?
  78. Have you seen my stripey scarf?
  79. Do you still love me?
  80. Could you please put the toilet seat down for once, you savage?
  81. Is this fancy enough?
  82. If a train leaves Station A at 1pm and reaches Station B at 6pm, and a second train leaves Station B at 3pm and reaches Station A at 6:30pm, at what time do the two trains meet?
  83. Does Saturday count as a business day?
  84. Will you remind me to take my birth control at 6?
  85. Did you set an alarm for tomorrow morning?
  86. What’s up?
  87. Why do you like so many pages on Facebook?
  88. How old were you when your balls dropped?
  89. Can we stop at the next rest stop so I can pee?
  90. Is your internet working?
  91. Who let the dogs out?
  92. Did you like the restaurant?
  93. Say whaaaaaaat????
  94. Do you think we’ll be invited to Megan’s wedding?
  95. Do I have time to take a shower?
  96. Why did you have to get involved?
  97. What’s that one song that’s like, about the girl who doesn’t want the other girl to steal her thunder, kinda goes like, laaaaa da da da a yaaaaa?
  98. What if we didn’t go to the thing tonight and just stayed in?
  99. Do you believe in Yetis?
  101. Are you still hungry?
  102. What do you get a thirteen-year-old boy for his birthday?
  103. Did you know using the term “spirit animal” is cultural appropriation?
  104. Why is “Internet” supposed to be capitalized?
  105. Why you gotta be so rude?
  106. Is it unethical to BCC my boss on this email?
  107. Do you think she’s pretty?
  108. Did Jack seem weird to you last night?
  109. Which one is Ashanti and which is Aaliyah?
  110. Have you seen this before?
  111. If you get queasy on a roller coaster is that technically “motion sickness” or does that only refer to like, mild motion like cars or airplanes?
  112. Do you think my toe could be broken?
  113. Does this sound dumb?
  114. Is periwinkle a blue or a purple?
  115. Why did the chicken cross the road?
  116. Wouldn’t it hurt YOUR feelings if I brought you to a thing and didn’t introduce you to anyone?
  117. What if we took a painting class together???
  118. Are you kidding?
  119. Do you mind if I call my mom real quick?
  120. What’s the worst that can happen?
  121. Do you know where we’re going?
  122. Do you want another drink?
  123. Are you feeling better?
  124. Is winning the lottery a good or a bad thing ultimately?
  125. But can you understand why it SEEMS like you’re mad at me?
  126. Can you hear me now?
  127. Isn’t that annoying?
  128. So what do you think?
  129. Isn’t life………… funny?
  130. Do I feel warm to you?
  131. Are you getting any phone service?
  132. Where does the phrase “cool as a cucumber” come from?
  133. You think you might get a haircut soon?
  134. Do you believe in life after love?
  135. Can I have a sip?
  136. Sorry, what?
  137. Does your mom like me?
  138. If I turn the ringer off on my phone, will my alarm still go off?
  139. Did you say something?
  140. Really?
  141. What do you think I should do?
  142. Is that her new boyfriend?
  143. What did they say?
  144. Do you think we would know if we were dead?
  145. Who’s on first?
  146. Is that a problem?
  147. What was in the FedEx box in Cast Away?
  148. Do I need to apologize?
  149. Did you call me earlier?
  150. Are you breaking up with me?


Once you’ve asked all these questions, you’re bound to have a more secure and informed relationship, which is all you really want! So, what are you waiting for? Get asking!