200+ Deep Conversation Starters – Talk Deep!

Deep conversations are those that go beyond the surface level of discussion. They are thought-provoking, intellectually challenging, and emotionally stimulating.

Engaging in such conversations can be a valuable way to gain a deeper understanding of ourselves, others, and the world around us. It can lead to self-discovery, personal growth, and even a shift in perspective. But what are some deep conversation topics and questions worth exploring?

Well, the possibilities are endless. From philosophy to politics, spirituality to science, and everything in between, there are no shortage of topics that can spark a high-level conversation.

The key is to approach them with an open mind, a willingness to listen, and a curiosity to learn. In this article, we’ll explore some examples of deep conversation topics and provide questions to help you dive deeper into them.


Deep Conversation starters

216). What has been the most difficult experience you’ve ever had?

215). If you could change one thing about the way you were raised, what would it be and why?

214). If you could ask a psychic one question about your future, what would you want to know?

213). What’s something you’re really good at?

212). What stresses you out the most when traveling?

211). What is the greatest accomplishment of your life thus far?

210). What is your most unique family tradition? What is your favorite family tradition?

209). What are the rules you want to establish at home? What would you do if someone broke one of them?

208). Tell me about a time you felt completely out of your comfort zone.

207). What do you consider to be the biggest mistake you’ve ever made?

206). What is your favorite memory of us?

205). If budget were no object, where would you go on vacation?

204). Where do you think your life is headed?

203). How would you be able to rank the following in importance: family, career, love life?

202). What book had the most impact on you in childhood?

201). What’s something that cheers you up when you’re sad?

200). Describe your perfect day.

199). Who is the person in your family you’re the most honest with?

198). Describe the physical touch that best communicates “I love you.”

197). What’s the biggest risk you’ve ever taken? Would you do it again?

196). Do you believe in twin flames?

195). Do you plan to take care of your parents in their old age?

194). What two big turning points in your life do you consider to be the most significant?

193). How does your family express love and affection?

192). In what ways are you most different from the person you were in high school?

191). Where in the world would you like to live? What’s the reason for it?

190). When you’re bored, what do you usually do?

189). What do you want to achieve in your life? What is the most important thing to you?

188). Tell me about the most recent act of kindness you did for a stranger.

187). Do you like to exercise? What’s your favorite form of exercise, if so?

186). When was the last time you put in a lot of effort?

185). What’s a very ordinary action that you find really attractive?

184). Who would you prefer if you had to choose a character from a book, movie, or TV show who is the most similar to you? Why?

183). What food or drink most evokes a feeling of home for you?

182). Tell me about your first heartbreak.

181). What rules or practices did your household follow growing up that you would also implement in your own household? What rules or practices would you choose not to follow?

180). What does it mean to be good in bed?

179). What are some of the things you remember that you’d rather forget?

178). If you were given one year to live, what would change about how you spend your time?

177). Tell me about someone you no longer speak to who you wish you were still friends with.

176). Tell me about two of your lifelong friends and why they matter so much to you. What factors made you choose them?

175). Would you rather have a simple task for someone else or a challenging job for yourself?

174). What’s your favorite thing to do by yourself?

173). What class or teacher most impacted your life growing up?

172). What have been the highest and lowest points of your life?

171). When was the first time you said “I love you” to someone who isn’t a member of your family?

170). If you could apologize to one person from your past, who would it be and why?

169). Do you play any sports? If so, which one?

168). Do you wish to be a parent? If so, why?

167). What is something you want to ask me but are afraid to ask me?

166). Should children help with household chores?

165). Name three things we have in common.

164). What is your predominant love language?

163). What did you enjoy doing as a kid that is no longer part of your life?

Deep Conversation Topics About Current Events, News & Social Media

162). Do you want to travel back to a time before the internet?

161). When is it the right time to quit social media?

160). What brought you to social media?

159). Are your priorities different from what they were 10 years ago?

158). If you’d be a reporter for this day, what will be its headline?

157). What’s one fear you want to master?

156). What’s your quirkiest habit?

155). How can you tell when you have chemistry with someone?

154). What was your favorite novel as a kid?

153). In all of history, who would you spend an afternoon with?

152). What animal would you want to be for a day, and why?

151). What’s the earliest thing you remember as a child?

150). How do news articles affect your daily life?

149). Do you tweet about how you usually feel?

148). What is so interesting about social media?

147). Have you ever thought of finding love on social media?

146). What are the current events that are deeply affecting your life?

145). How has news evolved over the past ten years?

144). What would be the topic of your New York Times bestselling book?

143). What book has influenced you the most?

142). What do you think the world would be like without news?

141). Have you tried hacking one of your ex’s accounts?

140). How long have you been in the social media world?

139). Has your character been shaped by anyone?

138). What’s your favorite memory of helping a stranger?

137). What would you use to describe social media in one word?

136). If you had a free hour, how would you spend it?

135). What do you like the most about being “you”?

134). If you could travel anywhere in the world for dinner, where would it be?

133). Do you think social media will still evolve in the future?

132). If you had paints right now, how would you fill a blank canvas?

131). What’s a recent lesson your parents/caregivers taught you?

130). What’s your greatest achievement so far?

129). Why do we need to know the latest news?

128). If you had a time machine, what year would you travel to?

127). What comes to your mind when you hear the word “Facebook”?

126). What’s the email address you currently use to log in on your Facebook account?

125). Can newspapers disappear in the future?

124). What news have you recently read?

123). Who’s your role model, dead or alive?

122). What’s a quote that inspires you?

121). What subject did you look forward to in school?

120). Have you seen funny videos from Facebook last night?

119). How do you define success?

118). What’s your #1 goal right now?

117). What is the cause of cruel behavior in the world?

116). What’s a quality you still want to have at age 90?

115). What song was last you played on Spotify?

114). Have you ever shared your Spotify playlist with someone you really love?

113). What’s the most awkward Zoom meeting you’ve ever had?

112). Do you spend your time mostly on social media platforms?

111). How do you usually take bad news?

110). Have you had any recurring nightmares?

109). What’s the best meme you’ve seen recently?

Deep Conversation Starters for Couples

108). Would you rather have a job you love with a lower salary, or a job you don’t enjoy with a higher salary?

107). Is there a place or a time in your life you wish you could return to?

106). Have you ever been to therapy or would you consider going to therapy?

105). Who do you think will be the most important people in your life 10 years from now?

104). Why do you think your past relationships didn’t work out?

103). What do you listen to when you’re driving?

102). Who is the most generous person you know?

101). Who in your life do you feel safest with?

100). Are you an optimist or a pessimist?

99). You’re stressed… how do you react in that moment and why?

98). Where do you feel most at home?

97). Which skill would you instead learn: oil painting outdoors, barefoot waterskiing, coding, or opera singing?

96). What do you sing in the shower?

95). Is it essential for you to fit in?

94). What do you value most about our relationship?

93). What makes you feel nostalgic?

92). Is there anything you would consider a deal breaker in a relationship?

91). What was the most significant trouble you got into in school?

90). Do you believe in love at first sight or the existence of soulmates?

89). What does it take for someone to be considered your best friend?

88). Which State would you visit if you could?

87). What do you think makes a long-term relationship successful?

86). Do you think happiness is overrated?

85). Is it better to share your emotions or keep them to yourself?

84). What are your financial goals for the future?

83). How do you define a healthy relationship?

82). Who makes you feel the happiest?

81). What do you like to listen to or watch when you’re cleaning?

Deep Conversation Topics to Ask a Girl

80). What are your thoughts on compromise in a relationship?

79). What do you most look forward to about getting old?

78). If you were an action figure, what accessories would you be sold with?

77). What do you think about communication in a relationship?

76). What do you think people automatically assume about you when they look at you?

75). If you could hear every time someone said something good about you or something negative about you, which would you choose?

74). If you were given $15,000 to give the most amount of happiness to the most amount of people, what would you do?

73). What role does sex play in a relationship?

72). What’s something you learned recently that you really should have already known?

71). What’s something horrible that we as humans have accepted, because that’s just how things are; but actually things don’t have to be that way at all?

70). What are your thoughts on compromise?

69). Do you prefer being warmed when you’re too cold or being cooled when you’re too hot?

68). What do you need in a relationship to feel fulfilled?

67). What’s the best piece of advice someone has given you?

66). What are your thoughts on intimacy in a relationship?

65). What are your deal breakers in a relationship?

64). What’s the best gag gift you’ve ever seen or gotten?

63). What are you most grateful for?

62). What snack can you just not get enough of?

61). What do you wish you could re-live in your lifetime?

60). What are your thoughts on trust in a relationship?

59). What are your thoughts on commitment in a relationship?

58). What are your thoughts on monogamy?

57). What’s the best practical joke you’ve pulled or seen pulled?

56). What’s your “and then it got worse” story?

55). What piece of culture or trend has died out, but you would like to see it make a comeback?

54). What kinds of things are normal now but will be highly valued antiques a century later?

53). What was something you ate regularly as a child but now cringe at the thought of eating?

52). When was the last time you laughed so hard you cried?

51). What are your thoughts on conflict resolution?

50). What’s an innocent mistake you made that had dramatic consequences?

49). What’s the craziest thing you’ve ever done for love?

48). What’s something weird that you recommend everyone trying at least once?

47). If you inherited a private jet from a stranger, what would you do with it?

46). Looking back on your life, what have you done that has given you the most satisfaction?

45). Have you ever trusted your boyfriend to buy clothes for you?

44). What are your thoughts on love and affection?

43). What do you need from me in a relationship?

42). How much time do you think a healthy relationship requires?

41). What would be the worst thing to put into a piñata?

40). Are you ready for a committed relationship?

39). What are you looking for in a partner?

38). What are your thoughts on sex and intimacy?

37). What are your thoughts on trust?

36How much effort do you think a healthy relationship requires?

35). Would you go through a boyfriend’s phone if you could?

34). What country can you name but besides the name you know almost nothing else about it?

33). Is flirting cheating?

32). What are your thoughts on conflict resolution?

31). What weird smell do you really enjoy?

Deep Conversation Topics to Ask a Boy

30). What are three occupations that machines will soon replace?

29). Who single-handedly changed the course of the entire human race?

28). Is human consciousness just electrons flowing through neurons, or is it something beyond the physical?

27). How do you build friendships with other guys?

26). What has had the biggest impact on your political beliefs?

25). Is poverty an inevitable byproduct of human society?

24). How do you think about women?

23). What would the perfect you be like?

22). Who should be responsible for taking care of the elderly, the government, their families, or the elderly themselves?

21). What do we do now that will be looked at as primitive and backwards in 100 years?

20). How do you feel about being responsible for pushing a relationship forward (e.g., asking a girl on a date or to marry you?)

19). What is your definition of being a man?

18). What event would you rather die than live through?

17). What human trait is useful now but would have been disadvantageous in the past?

16). Why do some people stay in relationships that they know are toxic?

15). Do you think humans will survive long enough to evolve into something different or will we make ourselves extinct before we have the chance to?

14). What do you think of society’s idea of what a man should be?

13). What stops people from understanding themselves?

12). What is the most worthwhile goal a person can dedicate their life to?

11). What’s your favorite thing about being a man?

10). Do you think morality exists in nature or is it a human construct?

9). Will technology be humanity’s salvation, downfall, or neither? Why?

8). If we could screen babies for psychopathic or sociopathic tendencies, should we? What should we do with the babies that are likely become psychopaths?

7). Why is depression so stigmatized in society?

6). What is deeply unsettling?

5). What’s your least favorite thing about being a man?

4). What do you consider a wasted life?

3). What do you think about expressing your emotions?

2). What do you think the challenges are of being a man in the modern world?

1). Do you ever feel pressure to be the provider in your family or relationship?

In summary

Exploring life’s depths through meaningful conversations is an important part of any relationship. Asking each other thoughtful questions helps uncover values and beliefs while creating a deeper connection between two people.

From discussing what gives someone satisfaction to exploring how they feel about manhood or morality, deep conversation topics can help take relationships to a whole new level.

Amy Klein

Amy Klein

Amy Klein is an accomplished writer and editor with years of experience in the anime and manga industries. She brings a unique perspective and deep understanding of the otaku subculture to her insightful and engaging writing, featured in various publications.

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