Conversation Starting Questions (for fun)

I was sitting there once with some family members, waiting in the hospital waiting room.  And it seemed like there wasn't much to do but wait and look at the television and wait some more.  Minutes turned to hours.  And I thought, Wouldn't it be great to have a book of meaningful questions that we could ask each other, just for fun and to hopefully learn more about each other and ourselves!  


I wanted to go to the bookstore and find a book like that, one that could help us pass the time and yet talk about meaningful things.  And then I thought, Why not write one myself?  And that's how this list came to be.

I love digging into deep conversations with others and learning more about what makes them tick.  I love exploring my life and myself and finding out what makes me who I am.  And that's what I'm hoping this list is - a tool to unlock deeper rooms of ourselves and to build relationships with other people.  I'd love for people to get engaged into more meaningful conversations with those around us.  I'd love to learn what goes on inside the heads of family and friends.  And I'd love to see people spend some more time getting to know themselves, because that's how I think true change and healing and searching happens.       

The way I see it, there are different ways to use these questions: 

#1  In private, in a journal, and for only for your own eyes.

#2  For spouses to do together to get to know each other better.

#3  For passing the time with friends.

#4  To get conversations going at family gatherings or as ice-breakers at parties.

#5.  At a “book club” kind of meeting where you get together with friends to discuss your answers.

#6  Or as a “family legacy” kind of thing where you record the answers of family members and pass it down to newer generations.       

(For the younger ones out there, those are not hashtags.  They're number signs.  I wrote this list before hashtags were a big thing.)


Whatever you do with it, you are bound to learn something about yourself or about others, or to at least pass the time in a meaningful way.  Grab a cup of coffee, maybe a friend or two, and enjoy a trip down memory lane.  (I know that all memories are not pleasant.  But I do think that it's important to explore all the things that made us who we are.  And so I do include questions that might hurt a bit to answer.  Skip them if you are not ready for them.) 

Daydreaming and Just for fun:

1.  If you could have any superpower, what would it be and why?

2.  If you could learn any skill or talent, what would it be?

3.  What time period would you love to be able to visit and why?

4.  What time period would you call "the worst time to be alive"?  “The best”?

5.  If you could plan a dinner party and invite any seven people, who would they be?  (Living or deceased.)  Why these people?

6.  If you could have anything named after you, what would it be? 

7.  If you had to change your name, what name would you pick?  What if you were the other gender?

8.  If you had to look like any celebrity, who would it be?  And who would it be if you were the other gender?  (And have you ever been told that you looked like any celebrity?)

9.  If you could meet any celebrity, who would it be?  Pick a male and a female? 

10.  What movie or show would you have loved to be in or to be a part of?  Why?

11.  What songs make you want to turn up the music and dance or sing out loud?

12.  If they made a movie of your life, who should play you?  What should the movie be called? 

13.  If you had three wishes to use for yourself, what would you wish for?  (Besides world peace and salvation for all.)

14.  If you had three wishes to use for others, what would you wish for?  (Besides world peace and salvation for all.) 

15.  Who in history do you most admire?  Why?

16.  Who in your life do you most admire?  Why?

17.  What would your perfect day be like?

18.  What is your ideal vacation?

19.  How do you like to spend your precious bit of "me-time"?

20.  Do you have any recurring dreams or nightmares?

21.  What do your daydreams typically revolve around?

22.  What five realistic things would you love to do before you die?  What five "purely daydreaming" things?

23.  Do you have any goal or dream that you are not pursuing, but wish you were?  What's stopping you?

24.  What are three "random acts of kindness" that would be fun to try?

25.  Do you have any big, selfless daydreams that you would love to get a chance to do?  (Adopting, becoming a missionary, starting a support group, rescuing animals, volunteering, etc.)

26.  What would your dream job be?  Or . . . If you didn't need to work for money, how would you like to spend your days?

27.  In one short sentence, how would you like to be remembered when you're gone (or what would you like your tombstone to say)?

28.  Is there any question that you always wanted to ask another person?

29.  If you had to offer unsolicited advice to the general public, what three things would you say?

What are the top three . . .

30.  Happiest moments or days of your whole life?  (Besides the big two: having children or getting married.)  

31.  Saddest moments or days of your life?  How have these affected you and your life? 

32.  Exciting times in your life?  (Besides having children and getting married)

33.  Times you were at your angriest?

34.  Times when you were afraid?

35.  Most surprising things that ever happened to you?

36.  Most embarrassing moments of your life? 

37.  Most peaceful times or moments in your life?

38.  Times you were most disappointed in yourself?

39.  Moments that you were the most proud of yourself?  (Proud in a good way, not a sinful, prideful way.)

40.  Biggest influences (people or events, good or bad) on your life?  How did they affect you? 

41.  Pet peeves that you have about what others do or don't do? 

42.  Things that really get you worked up into an angry fit?

43.   Things about this life that make you heartbroken and want to cry?

44.  Movies, books, or songs that you love?  What is it that you like about them so much?

45.  Movies, books, or songs that you hate, and why?

46.  Movies, books or songs that really touch your heart or make you want to cry?

47.  Little indulgences that you like to treat yourself to?

48.  Guilty pleasures that you don't readily admit that you like?

   

49.  Things that most people don't know about you? 

50.  Most touching things someone has ever done for you? 

51.  Most thoughtful things you've tried to do for others?

52.  Little things that always make you smile?

53.  Big things that bring tears of joy to your eyes and make your heart want to burst? 

Looking Back:

54.  What are your earliest memories?

55.  How would you describe your childhood/your family-of-origin?

56.  What were some of your favorite things about your childhood? 

57.  What were some of your least favorite things? 

58.  What were your happiest moments or days from when you were young?

59.  What were your saddest moments or days from when you were young?

60.  When did you laugh the hardest in your lifetime?  

61.  When did you cry the most?

62.  When were you the most exhausted you have ever been?

63.  When you were young, what were some misconceptions that you had about life or people?

64.  What truths or "truths" did you learn way too early?  How has that affected you?

65.  What was the best friendship that you ever had?  What made it the best?

66.  When you look back on your childhood friends, what did you learn from each of them, how did they change you, or what did they contribute to your life?

67.  When you were young, what did you want to be when you grew up?

68.  When you were young, what did you wish your parents had named you? 

69.  Do you have any little regrets?

70.  Do you have any big regrets?

Changes:

71.  If you could make or change any three laws for our country, what would they be?

72.  If you could take back any moment of your past or go back and do something over again, what would it be?

73.  If you could change three superficial, non-essential, just-for-fun things about yourself what would they be?

74.  If you could change anything in general about your past/childhood, what would it be?

75.  If you could change three deep things about yourself or your life, what would they be, why would you change them, and what would you change them to?

76.  What do you wish your mother and father had done more of as you were growing up?  

77.  What do you wish they had done less of or not at all as you were growing up?

78.  What might your kids or spouse or significant other say that they wish you would do more of?  Less of or not at all? 

79.  Were there any opportunities that you didn't take but wished you did?

80.  Were there any that you took and wish you didn't?

81.  Is there any relationship that you would change right now?  How and why would you change it?

82.  What are three bad habits/tendencies that you wish you could stop?

83.  How do you waste time, in good or bad ways? 

84.  What are three good habits/disciplines that you wish you could add or start?

85.  How would you like your life to be different one year from now?  Ten years from now?

86.  What do you hope never changes about your life?

Searching our Hearts and Minds:

87.  When you are letting your mind wander, where does it usually go? 

88.  Are there things from your past that you haven't dealt with or let go?

89.  Dig deep . . . What is something that you are bitter about right now?

90.  What are you angry about right now?

91.  What are some unanswered questions that you are currently struggling with? 

92.  What are some doubts and/or fears that you are currently struggling with?

93.  How do you think of/feel about yourself?

94.  What five things do you like most about yourself?  What three things do you like the least?

95.  How do you think others would describe you?

96.  What three things do you think others like the most about you?

97.  What three things do you think others like the least about you?

98.  What are some things that you know you need to change?

99.  What are some common misconceptions about you and what is the truth?

100.  Was there ever a time that you knew "the good you were supposed to do," but you didn't do it?

101.  Are there things that you regularly avoid doing that you know you should do?

102.  Are there things that you regularly do that you know you shouldn't be doing?

103.  What are the top three things that you are proud of - in a prideful, smug way? 

104.  What are the top three idols in your life right now (things that you are taking your focus from God)?

105.  When it comes to being more loving, joyful, peaceful, patient, kind, thankful, faithful, gentle, content, full of self – control, or being less jealous, boastful, or prideful, which are the top three that you need to work on?

106.  What are your three biggest fears when it comes to life?  Where did these come from?

107.  What's the top three best pieces of advice you have ever been given or gathered?

108.  What are the top three best guidelines or mottos you try to live by?

109.  What are some disciplines that you currently have that help you a lot?  How do these benefit you?

110.  What are some things that you are passionate about?

111.  If you had to make five resolutions concerning the rest of your life, what would they be?

112.  If you asked your parent, best friend, spouse or a different significant other, what would they say your top five resolutions should be?

Relationships:

113.  Do you believe in marriage?  Why or why not?

114.  What does love look like to you? 

115.  What are the five most essential ingredients for a successful relationship/marriage?

116.  What are some expectations that you have when it comes to relationships?  How do you feel/think when these are not met? 

117.  Could you lower these expectations or drop them altogether and still feel like the relationship was "worth it"?

118.  What do you do that bothers or annoys your significant other?  Why do you keep doing these things?  And how could you change them, if you really tried?

119.  Is there some elusive quality that you seem to always be searching for or trying to cultivate in your significant other or your relationship?  How is this working for you or affecting you and your relationship?

120.  What are your three biggest fears when it comes to relationships?  Where did these come from?

121.  If you just arrived at a party, what would you most likely do first and how would you typically act the rest of the evening?

122.  What are some of the typical ways you interact with people?  Why do you act this way? 

123.  What kinds of people do you try to avoid or least like being around?

124.  What kinds of people do you like to be around? 

125.  What are some of the things you would change about the way you interact with others?  How would you like it to be instead? 

126.  What are some ways that you sabotage relationships?

127.  What are some things that you complain about the most or get upset about when it comes to relationships?  Do you have any role in causing this or in preventing it from being any different or better?

128.  Is there someone you have never forgiven?  What effect has that had on you and your life?

129.  Is there someone you've never asked for forgiveness from?  How has that affected you and your life?

130.  Is there anyone that you would love to reconnect with?

131.  What do you hope people forget about you when you are gone?

132.  What do you hope people remember about you when you are gone?

133.  Are there any qualities that you are trying to cultivate in your family or want to when you have one?

 

Godly thoughts:

134.  Do you believe in God?  Why or why not?

135.  Describe a time when you really felt the presence of God.

136.  Have you ever had a time when you experienced the presence of evil?

137.  Do you think that you ever had an encounter with an angel or angel in disguise?

138.  Is there a time that you desperately wanted or needed to feel God's presence, but didn't?

139.  Have you ever experienced what you consider a miracle or had a supernatural experience?

140.  Have you ever had any dreams/nightmares that were very significant or that you thought had a deeper meaning?

141.  How would you describe God?  (Not what you have been taught to think of Him or what the Bible says of Him; but what ideas of Him have you grown up with or developed?)  And what do you think He expects out of people?

142.  How do you describe faith?

143.  When do you feel closest to God?

144.  If you could ask God any five questions, what would they be?

145.  Is there anything that you are angry or disappointed with God about?

146.  Do you think that He is angry or disappointed with you about anything?

147.  If you were to meet God now, what do you think He would say to you?

148.  Are there any messages from Him that you think He's been trying to get through to you?  What prevented you from acknowledging them until now?

149.  What are your three biggest fears when it comes to God?  Where did these come from?

150.  Do you have any unanswered questions about God and faith that you just can't seem to find answers for?  How has that affected you and your relationship with God? 

151.  What do you think happens when people die?

152.  What do you think Heaven is like?

153.  What do you think Hell is like?

154.  In your mind, what does it take to get into Heaven?  And if you could choose to go to Heaven, would you? 

            [I believe that we do choose if we go to Heaven or Hell, if we spend eternity with God or without.  To see my view on this, look up the post "Starting Your Own Relationship with Jesus Christ."  It is so important to have a clear understanding of this.]