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200 (Not Boring) Questions To Ask To Get To Know Someone Better Pt 3

Turning small talk into real talk.


Part 3 of “Questions” starts with digging deeper into someone’s values.

“In learning about someone’s values, you are learning about their owner’s manual,” Hendrix explains. Even seemingly mundane questions can get at a person’s values—like what’s motivating them to do well on a presentation or what they look for in an S.O.

“By learning about someone’s life philosophy, you’re able to get at their true essence, how they live their life, and what drives their actions,” Orbuch adds.

That said, you can’t just ask, “What are your values.” What you can ask:

121. What’s a relationship deal breaker for you?

122. If you had only one sense (hearing, touch, sight, etc.), which would you want?

123. What is your definition of success?

124. Are you at all religious or spiritual?

125. What are you most proud of in the last year?

126. What makes you feel most accomplished?

127. Who do you admire most in the world?

128. If you won a million dollars, what would you do with the money?

129. Which of your personality traits are you most proud of?

130. What’s the first thing you look for in a partner and/or friend?

131. How did you form your current political views?

132. Do you live by any piece of advice or motto?

133. How can someone earn your trust?

134. How can someone lose your trust?

135. Would you rather someone be honest and hurt your feelings or lie to protect them?

136. If you could snap your fingers and instantly make the world better, what would you do?

137. Do you believe in astrology? Why or why not?

138. Have you ever lost a friend? If so, what happened?

139. If you could only teach one thing to your (future) child, what would it be?

140. What’s the scariest thing you’ve ever done, and why did you do it?

141. Do you believe in second chances?

142. Where do you get your news?

143. What is your biggest irrational fear?

144. Do you contribute to any charities?

145. When was the last time you volunteered?

144. Are you an organ donor?

145. Do you believe you should do one thing a day that scares you?

146. What, if anything, do you think happens after death?

147. What line should someone never cross with you?

148. How do you define beauty?

149. Do you believe in life on other planets?

150. How do you interact with someone who disagrees with you?

As promised:


“These questions get at what the person is motivated by,” says Orbuch. “What gives them the strength to wake up every day and get going? What do they dream and think about in their day?” When you learn about someone’s dreams, you share something more intimate. Jumpstart a deep conversation by asking this:

151. If you could do anything, besides what you’re doing now, what would you do?

152. What do you regret not doing in the last year?

153. What’s on your bucket list?

154. If you had unlimited money to start your own business, what would it be?

155. If you found out today was your last day on Earth, what would you do?

156. If you could live anywhere in the world, where would it be?

157. A genie gives you three wishes—what are they?

158. If you had the opportunity to be immortal, would you take it?

158. Which famous person in history would you want to spend the day with?

157. If you could time travel, when and where would you go?

158. Do you think you’ll likely accomplish all your dreams?

159. If you could magically become famous, would you want to?

160. If you could relive one moment in your life, which would it be?

Last, we have:

Unconventional questions

Sometimes the oddball questions allow you to learn the most interesting things about a person. “Unusual questions allow you to see the varied, unique, and special qualities of a person—their answers give you personal information about what makes them tick,” Orbuch says. “These questions also typically get the other person to think outside box and really ponder something.” Ask these ~unconventional~ questions, and you’ll definitely get some surprising answers:

161. If you see a puddle on the ground, do you walk around it or over it?

162. If you could have a super power, what would it be?

163. If you could go back to anytime in history, where would you go?

164. If you came back in your next life as an animal, what animal would you be?

165. If you got to name a new country, how would you decide what to call it?

166. What would be the title of your memoir?

167. Do you hit the snooze button or wake up immediately?

168. What’s the first thing you do in the morning?

169. What’s the last thing you do at night?

170. Do you believe in any conspiracy theories (no judgement)?

171. Do you think iced coffee should only be consumed in the summer or all year round?

172. Would you rather be covered in fur or covered in scales?

173. What’s your idea of a perfect date (yes, of the calendar year)?

174. What’s the most unusual place you’ve fallen asleep?

175. At a party, where can someone find you?

176. Do you wash your legs in the shower?

177. Who would play you in the movie of your life?

178. When making a PB&J sandwich, do you put on the peanut butter or jelly first?

179. Do you have any allergies?

180. Do you trust your own memory? Why or why not?

181. Which fictional character do you relate to most?

182. What, if anything, would make you walk out in the middle of a movie?

183. When was the last time you cried and why?

184. What’s your most controversial opinion?

185. Do you “stan” any celebrities?

186. What’s your go-to drunk snack?

187. What was your all-time favorite Halloween costume?

188. What’s the weirdest thing you do when you’re alone?

189. Do you have any recurring dreams?

190. What’s the silliest argument you’ve ever been in?

191. What’s the worst argument you’ve ever been in?

192. What’s your opinion on modern art?

193. If you could choose how to die, would you? If so, what would you choose?

194. What’s the most ridiculous outfit you’ve ever worn?

195. What was the first thing you wanted to be when you grew up?

196. If you could own a mythical creature (unicorn, phoenix, etc.), which one would you pick?

197. What’s your least favorite place in the world?

198. Would you rather have your dishes or clothes be magically clean?

199. What’s your favorite story about yourself?

200. If you could change anything about yourself, would you? If so, what and why?

“Anytime you reveal personal information to someone else, it increases intimacy between you and the other person,” says Orbuch. So let down your guard, and don’t be afraid to ask (or answer!) these deep questions.

So, there you have it, 200 questions to ask someone to get to know him/her better.  

Macaela Mackenzie is a freelance journalist specializing in health, culture, and tech, and she regularly contributes to outlets like Prevention, Women’s Health, Shape, Allure, Men’s Health, the John Hopkins Health Review, and more.
Lindsay Geller is the Associate Love & Lifestyle Editor at Women’s Health.

200 (Not Boring) Questions To Ask To Get To Know Someone Better Pt 2

Turning small talk into real talk.

Let’s continue with the next series of questions on getting to know someone better.


No matter how a person feels about his or her job, the fact is, pretty much everyone spends a lot of time and energy at work. To help you get to know someone better, “facilitate a conversation where you are left knowing how they feel about their career,” Hendrix says. For example:

41. What’s your favorite thing about your current job?

42. What annoys you most?

43. What’s the career highlight you’re most proud of?

44. Do you think you’ll stay at your current company awhile? Why or why not?

45. What type of role do you want to graduate to after this one?

46. Are you more of a “work to live” or a “live to work” type of person?

47. Does your job make you feel happy and fulfilled? Why or why not?

48. How would your 10-year-old self react to what you do?

49. What do you remember most about your first job?

50. Did you start working immediately after finishing school? Why or why not?

51. What’s the worst job you’ve ever had?

52. What originally got you interested in your current field of work?

53. Have you ever had a side hustle or considered having one?

54. What’s your favorite part of the workday?

55. What’s the best career decision you’ve ever made?

56. What’s the worst career decision you’ve ever made?

57. Do you consider yourself good at networking?

58. What career advice would you give to your younger self?

59. Do you believe in having a “five-year plan”?

60. How do you separate your work life from your home life?

61. When will you know you’ve “made it”?

62. Are you looking forward to retiring, or do you plan to work as long as possible?

63. Have you ever had “imposter syndrome”?

64. What do you think about workaholics?

65. What qualities do you look for in a boss?

66. Do you have a professional mentor? If not, do you want one?

67. Do you have a work best friend?

68. Are you into after-work happy hours?

69. How do you motivate yourself in your career?

70. What’s the best career advice you’ve ever heard?

71. What’s the worst career advice you’ve ever received?

72. When you started your current job, what most surprised you?

73. How do you pick yourself back up after making a mistake at work?

74. How do you deal with work stress?

75. What energizes you about your career?

76. What’s one work-related thing you want to accomplish in the next year?

77. Who has had the biggest impact on your career choice?

78. What does your family think of your career?

79. What’s the best thing you’ve learned in your current position?

80. If you could do it all over again, would you pursue the same career? Why or why not?


A great way to get to know someone on a more personal level? Learn about the people they love. “Asking questions about close relationships can lead to stories, and sharing stories leads to connection and an experience of being seen by one another,” Hendrix explains. Try:

81. How much time do you spend with your family?

82. Who do you most like spending time with and why?

83. Were you close with your family growing up?

84. How do you define your family now?

85. What traits are most important to you in your family members?

86. Who are you the closest to and why?

87. Do you want a family of your own?

88. What’s your favorite family tradition?

89. If you could change your relationship with a family member, would you? If so, with whom?

90. What was it like growing up as the youngest/oldest/only child?

91. Does your family take vacations together?

92. What’s your favorite family memory?

93. What TV family most reminds you of your own?

94. Do you ever wish you were raised differently?

95. What’s the best piece of advice a family member has given you?

96. Do you wish you had more siblings? If so, why?

97. Did you ever hide anything from or lie to your parents?

98. If you had a family business, what would it be?

99. Do you and your family have any nicknames for each other?

100. What’s your favorite way to spend time with your family?

101. How do you show your family you love them?

102. Have you ever been to a family reunion?

103. What’s the most important holiday you spend with your family and why?

104. Who in your family would you describe as a “character”?

105. How do you feel about family events?

106. What’s something your family would be surprised to learn about you?

107. Which family member do you confide in most?

108. How do you deal with arguments between family members?

109. If you have children, how do you want to raise them?

110. What’s more important: family or friends?

111. Do you have any friends you would consider family?

112. Has your family ever pressured you to act a certain way?

113. Did you ever get to meet your great-grandparents?

114. What personality traits do you share with your relatives?

115. What physical traits do you share with your relatives?

116. What stories did your family members tell you growing up?

117. How did your parents (and/or grandparents) meet?

118. What makes you proud of your family?

119. Who’s the newest member of your family?

120. What can always bring your family together?

And that’s enough for today.  80 more questions to go.   You’re probably seeing these questions in your dreams.  Oh, gave away some of tomorrow’s questions.  See you then.

These Game of Thrones Spinoffs Would Be Very Entertaining

By Evan Romano & Men’s Health Magazine

I dare you to not be intrigued by ‘The Westeros Wing’

Who’s feeling withdrawal? Anyone? Bueller?

The Game of Thrones finale is still fresh in everyone’s minds, and while mindlessly hating on the show seems to be all anyone wants to do today, in a couple of days or maybe a week, everyone will start feeling the pain of a Thrones-less existence—probably right around the time when they start their post-Thrones binge of a significantly-lesser show.

While a number of Game of Thrones spinoff ideas have reportedly been floated, one has moved forward in the development process—a prequel, supposedly focusing on the very first Long Night. While I have my own reservations about The Night King, that series has locked Naomi Watts into place, which is a spectacular piece. With her role in Twin Peaks: The Return, she already knows how to fit right into a beloved series with a tone that fans and critics are already very accustomed to.

That being said, the actual Thrones finale left plenty of our favorites in positions where we’d more than likely be willing to join them for a whole ‘nother series. Let’s take a look, shall we?

1 ‘Arya The Explorer’

Arya game of thrones spinoff 

Let’s start this list off in earnest: This show would be such a blast. Already endorsed by the literary horror/adventure master himself, this show could follow Arya’s post-Thrones adventures, get extremely dark and creepy, and be an obvious winner.

While the show cleaned Arya up more and more over the last couple of seasons into more of a prototypical good-guy protagonist, let’s not forget that there were a few seasons where she was a morally ambiguous killer. Oh yeah, and she can also shape-shift and wear the faces and identities of people she murders. Action/Horror meets Thrones meets Kill Bill, anybody?

2 ‘Tormund + Snow’

jon snow tormund spinoff

Much like this summer’s upcoming Hobbs & Shaw, this is a dream action pairing. With the finale setting this power duo up to take care of business up north, you just know that they are ready to kick ass, take names, and maybe even drink some giant’s milk.

Both feared and mighty warriors, these two may have different approaches to their craft, but you know they’re going to come together victorious and on the same side when it’s all said and done.

Not to mention both men are once again single—coming off blonde-induced heartbreak. The possibilities for Tormund & Snow are pretty much endless.


3 ‘The Westeros Wing’/’Hand’

hbo game of thrones spinoff tyrion

The Thrones finale gave us a pretty sweet set-up in King’s Landing with the possibility for two shows in one, with Tyrion Lannister the lynchpin of both.

First and foremost, it’s impossible to ignore the possibility of what The Westeros Wing could be. With the sharp tongues of Tyrion, Bronn, and Davos all sitting on the Small Council, the dialogue opportunities are endless. Aaron Sorkin is probably salivating and the simple thought of those three in a walk-and-talk, while figuring out how to solve the great budget crisis of the six kingdoms.

Within the same conceit, we have Hand, which follows a second-in-command (Tyrion), sick of his role doing all the work while the leader in name only gets all the credit. Like Veep before it, Hand will star a multi-time Emmy winner in a role that will undoubtably bring the opportunity for several more.

With his team behind him, the half-hour comedy Hand finds its foul-mouthed lead constantly scheming and berating his staff as he tries to find ways for more notoriety and more power.

4 ‘Jin Davra Place’

daenerys spinoff good place fun 

In a twist that was foreshadowed for much of the series and particularly the final season, Daenerys Targaryen was unable to avoid the same path as her father, becoming ‘The Mad Queen,’ murdering countless innocent people, and forcing Jon Snow to assassinate her to save the rest of the realm.

In ‘Jin Davra Place’—that’s Dothraki for ‘The Good Place,’ of course—we follow Daenerys as she first lands in the afterlife. She still thinks she was doing the right thing! She has no idea what hit her! So is this The Good Place or The Bad Place? That’s up for her to find out. Guest star opportunities run aplenty: Ser Jorah, Theon, Missandei—the list goes on.

She may not have gotten to spend time in Westeros with Jon Snow, but maybe in Jin Davra Place, she can link up with his half brother, Robb.

(Whose with me, Throne of Dragons) ?

Evan is an associate editor for Men’s Health, with bylines in The New York Times, MTV News, Brooklyn Magazine, and VICE.


200 (Not Boring) Questions To Ask To Get To Know Someone Better

Turn small talk into real talk.

By Macaela Mackenzie and Lindsay Geller

Sometimes, you meet someone, and you just click. You feel like you’ve been besties your entire life and honestly can’t believe there was a time when you didn’t even know they existed. And then, there’s those other relationships that take a little more work—i.e., how it feels like pulling teeth to learn anything about your brother-in-law. While you might never be BFFs with your BIL, there is a trick you can use to get him to open up a little more.

Terri Orbuch, PhD, author of 5 Simple Steps to Take Your Marriage from Good to Great, says getting to know someone starts with the “breadth questions”—think: impersonal but important biographical info like where someone is from, where they work, if they’re single or married, etc.

But if you really want to get to know someone beyond the surface level, you’ve got to dig deeper. “Topics that get at the other person’s inner world—their thoughts, goals and dreams—will strengthen and increase bonding between two people,” Orbuch says. “Just like in a romantic relationship, sharing personal information strengthens the relationship—deeper questions focus on that personal self-disclosure.”

Move past the small talk ASAP, and ask these 200 questions instead.  (Let’s do this in bite-sized chunks.  No need to rush with all 200.)


“Asking someone about their preferences helps you to understand who they are as a person,” says Rebecca Hendrix, a therapist in New York. The important thing here is to go deeper by asking follow-up questions.

For example, “if you find out they like dogs, take it a bit deeper by asking them what they like most about their dog,” Hendrix explains. “In answering, they are revealing a little more about themselves.” Some other ideas:

1. What’s your favorite way to spend a weekend?

2. What type of music are you into?

3. What was the best vacation you ever took and why?

4. Where’s the next place on your travel bucket list and why?

5. What are your hobbies, and how did you get into them?

6. What was your favorite age growing up?

7. Was the last thing you read digitally or in print?

8. Would you say you’re more of an extrovert or an introvert?

9. What’s your favorite ice cream topping?

10. What was the last show you binge-watched?

11. Are you into podcasts or do you only listen to music?

12. Do you have a favorite holiday? Why or why not?

13. What’s your “Death Row Meal“?

14. Do you like going to the movies or prefer watching at home?

15. What’s your favorite sleeping position?

16. What’s your go-to guilty pleasure?

17. In the summer, would you rather sleep with the window open or blast the AC?

18. What’s your favorite quote from a TV show/movie/book?

19. How old were you when you had your first celebrity crush, and who was it?

20. What’s one thing that can instantly make your day better?

21. Do you have any pet peeves?

22. Which meal is your favorite: breakfast, lunch, or dinner?

23. What song always gets you out on the dance floor?

24. When you were a kid, did you eat the crusts on your sandwich or not?

25. What activity instantly calms you?

26. Ideally, how would you spend your birthday?

27. What do you do on your commute to/from work?

28. Do you have a favorite type of exercise?

29. What’s your favorite season and why?

32. Would you rather cook or order in?

33. Have your ever disliked something and then changed your mind?

34. What’s your favorite board game?

35. How do you take your coffee?

36. What’s your most prized possession and why?

37. Is there any product that you couldn’t live without?

38. Do you sleep with a top sheet? Why or why not?

39. If you could have any exotic animal as a pet, which would it be?

40. Would you rather spend a day at the beach or poolside?
OK.  This is a good place to stop for today.  Tomorrow,  questions about careers and families.