Deep Questions: Questions to Get to Know Someone Deeply

Deep and meaningful questions go beyond dry facts, straight to the heart of a person. You use deep questions to get to know someone on a more profound level in an open-ended way by exploring their values, their passions, how they shape their inner life and what core beliefs drive them. 

People use these questions to get to know someone deeply, so it requires the right frame of mind and some vulnerability. This is why it’s always best to use them with people you already have a somewhat established relationship with. You can also use them during the later stages of a small talk interaction as a way to shift into a conversation that feels more intimate and emotionally rewarding.  

You can use deep questions to ask people to trust you with some of the deeper aspects of their lives, which means you should resist passing judgment or reacting negatively. They also help you express your curiosity and interest towards others, which helps develop more complex emotional connections. The great thing about deeper questions is that they lead to deeper conversations, which can often be a source of insight and self-discovery.

There are different things to ask to get to know someone, depending on the effect you want it to have and the context of the interaction. There are deep questions you ask a partner to build a stronger bond, ones that you can ask on dates to progress the interaction, enquiries into your friend’s lives that help deepen your friendship and even deep questions you can pose to yourself as an introspective exercise.

We explore these various types of serious questions, their effect and picking the right time and context to use them.

Good deep questions

What makes a meaningful question good is often less a matter of the question’s content and more how that question was phrased. It also includes other aspects like timing, context and appropriateness, which we explore later. But to put it more simply, you can tell how good a deep question is by the kind of response it gets. 

The deep questions you ask shouldn’t be motivated by any goal other than a genuine desire to understand the people in your life better. Approaching it from this perspective will naturally make your questions come across more thoughtfully, empathetically and feel sincere. In this sense, you could say that a good deep question simply comes from the heart. If you have some intimacy and trust, there’s seldom a bad time to ask a well-crafted, serious question. But try not to let it interrupt an active and positive conversation that has a different tone. Conversations have natural peaks and valleys. The best time to drop a good deep question is in the valley portion of the exchange.

1. What’s a lesson you learned the hard way that shaped who you are?
2. What’s something you’ve never told anyone but think about often?
3. What do you think is your most underrated quality?
4. What moment in your life felt like a turning point?
5. What do you wish you had more courage to do?
6. What keeps you motivated when you want to give up?
7. What do you think people misunderstand most about you?
8. What’s the hardest truth you’ve had to accept?
9. What makes you feel truly alive?
10. If you could ask the universe one question, what would it be?

Generally, the best deep questions to ask are the ones that have the obvious goal of wanting to understand someone better. Even if you’ve been friends or in a romantic relationship for decades, there are always hidden aspects of people in your life waiting to be revealed. It can have personal benefits, as a study published in the Journal of Educational Sciences & Psychology found that curiosity was strongly associated with overall life satisfaction.¹

Using deep questions to ask people about more personal aspects of their lives works so well because they don’t rely on a social mediator, such as humor or scenario building, to explore someone’s inner thoughts. By being sincere and upfront with a personal deep question, you wear your heart on your sleeve, immediately coming across as more honest and trustworthy.    

These questions aren’t simply limited to the initial fact-finding phase of the relationship. You will probably ask fewer of the questions we’ve included as your relationship matures but try to make curiosity part of your communication style as a couple.

11. What belief do you hold that you think not many people agree with?
12. What’s one memory that you think defines who you are?
13. Do you think your childhood shaped you more positively or negatively?
14. What’s something you’re still healing from?
15. Do you think people are mostly good or mostly selfish?
16. What’s a choice you made that changed your life forever?
17. What do you think is the key to truly knowing someone?
18. If you could relive one day, just to feel it again, which would it be?
19. What scares you about the future?
20. Do you think people are more shaped by love or by pain?

Questions to ask a guy to get to know him deeper

When it comes to the right deep questions to ask a guy, someone’s attachment style can often have a large impact. Make sure to shape your questions so they’re individualized to the person.

This doesn’t mean asking about sports or other classically “male” topics but rather acknowledging and exploring how men’s experiences may be distinct from yours. Questions are important in this way because they aren’t simply a request for information but a message in and of themselves. A study published in the Sex Roles journal found that men tend to approach conversation with different goals than women. Asking him one of these questions can help you break through this distancing behavior and get to the part where you’re truly exchanging instead of softly prodding each other’s boundaries.

21. What responsibility do you take most seriously in life?
22. Do you think vulnerability is a strength or a weakness?
23. What’s something you want to be remembered for?
24. Do you feel pressure to live up to expectations?
25. What was the last thing that genuinely scared you?
26. What does masculinity mean to you?
27. What do you want your legacy to be as a man?
28. Do you find it easy to open up emotionally?
29. What’s the bravest thing you’ve ever done?
30. Who’s been the most influential person in your life and why?

Deep questions to ask a guy before dating

These are very important questions because their answer can often be the deciding factor in whether or not you should choose to date a guy or not, regardless of noticeable chemistry and compatibility. They speak to your values, dating style and relationship deal breakers, so these are the deep questions to ask a guy.

The upside of men tending to maintain more emotional distance early in relationships is that you can be more direct with them. For instance, it wouldn’t be seen as unfair to bring these questions up in the same conversation where you explore taking the next step in the relationship.

This doesn’t mean the conversation has to be unpleasant or unengaging. Try one of these examples to address important aspects of your dating green and red flags in a way that feels respectful and authentically curious. 

31. What’s a relationship lesson you’ve carried into your adult life?
32. What are your long-term priorities outside of dating?
33. Do you think commitment is about choice or about feelings?
34. How do you handle disappointments in relationships?
35. What scares you about falling in love?
36. Do you believe two people need similar values to last?
37. What do you think is the hardest part of dating today?
38. How do you balance independence with being in a relationship?
39. Do you believe in timing when it comes to love?
40. What’s a deal breaker for you that people don’t expect?

Questions to ask a girl to get to know her deeper

The right deep questions to ask a girl are about really getting to know how she thinks. How and when you ask a question can have just as much influence on the response as its content. The reason for this was explored by the same study as above. It found that women tend to approach conversation in a way that focuses on building rapport and fostering connectivity.² However, this behavior is socialized, not innate so it’s not a completely reliable indicator of the reaction you’ll get.

By asking some of the questions below, you’re not just gathering facts but also communicating to the woman that you’re invested in being an engaging and respectful partner in conversation.

41. What makes you feel the most seen and understood?
42. Do you think vulnerability is difficult for you?
43. What’s something you long for that people might not know?
44. What’s a way you express love that isn’t obvious?
45. What experience made you realize you were stronger than you thought?
46. What’s something you’re proud of but rarely share?
47. Do you think you’ve found your purpose yet?
48. What’s the most meaningful compliment you’ve ever received?
49. What’s a value you won’t compromise on?
50. Do you think love can change people?

Deep questions to ask friends

These are the kinds of questions that are designed to gain a deeper understanding of your friends and create bonding opportunities. These can be particularly useful with newer friendships, where you’re still defining your communication dynamic, or with good friends as a way to introduce a more meaningful component in how you interact.

Deep talk and questions for friends can cover a range of topics. You can start slowly by just asking about their family or personal history more often. This is a good way to express that even though you’re already friends, you still appreciate their presence in your life and want to have a more profound presence in theirs. Depth often doesn’t seem as important in friendships as it is in romantic relationships, but it very much is. That is, if you want your platonic relationships to evolve and develop over your life. Try asking your friend at least one of these deep questions – or a more personalized one of your own – the next time you meet up. And be consistent. Make it a natural part of how you two interact.

51. What do you think friendship means at its core?
52. What’s a way I could be a better friend to you?
53. Do you think our friendship has changed over time?
54. What’s one of your favorite memories with me?
55. Do you think friends should always be honest, even if it hurts?
56. What’s a moment in your life when friendship really saved you?
57. Do you believe friends should have the same values to last?
58. What’s the most thoughtful thing a friend has done for you?
59. How do you know when a friendship is worth fighting for?
60. Do you think distance weakens or strengthens friendships?

Deep questions to ask your best friend

Your best friends will have a very different relationship with you. One that’s often more akin to a family member. For this reason, your dynamic often feels very much set in stone, particularly if your friendship goes back to your formative years. But it’s not. Friendships evolve just like any other relationship. Asking deep questions is just taking a more active and positive role in that process. 

Finding deep questions to ask your closest friends can often shake you both out of the interactional scripts you’ve both come to develop with each other. This isn’t to say these scripts aren’t also rewarding but asking meaningful questions shows that you’re checking in with them. It restates your commitment to the friendship and expresses that you are and always will be deeply invested in their life and emotional universe.

Try one of these examples or anything deep that’s on your mind, the next time you’re talking to one of your best friends. The great thing about close friendships is that there’s ample room for error.   

61. What do you think makes our bond unique?
62. What’s something you’ve wanted to tell me but never have?
63. Do you believe best friends can outgrow each other?
64. What’s your favorite inside joke we have?
65. When have I been there for you in a way you’ll never forget?
66. What scares you about the future, and do you want me to support you through it?
67. What’s something you admire in me that you’d never say out loud?
68. What’s the hardest part about being best friends?
69. How do you think our friendship has shaped who you are?
70. What’s one dream you want me to always remind you to chase?

Deep questions to ask your friends about yourself

No one knows you better than your friends and the people closest to you in life. These are the kind of deep questions that can help you explore aspects of yourself from an outside perspective. We often think we’re quite good at introspection and judging our own mental state. This cognitive bias is called the introspective illusion, where overrelying on the power of introspection has been found to be a significant barrier to self-knowledge,³ ironically enough. 

Coming up with some deep questions to ask the people in your life about yourself can be a mental health exercise to get insights into the things that have been bothering you. Getting some perspective from people who you trust and know care for you also helps ensure that these insights are shared with love and come from a genuine investment in your happiness and success.

Try not to bombard your friends with these questions, though, unless you’ve prearranged the interaction with the express purpose of exploring your issues. Here are a few questions to get you started. 

71. What’s your first impression of me versus now?
72. Do you think I listen well when you talk?
73. What’s a strength you see in me that I don’t?
74. Do you think I’ve changed since we met?
75. What’s a habit of mine you think is holding me back?
76. What do you think my love language is?
77. Do you think I handle stress well?
78. What’s something I’ve done that made you feel valued?
79. What do you think I could work on as a friend?
80. What’s a compliment you’d give me if I asked directly?

Deep questions to ask your partner

These questions are designed to help you and your partner explore deeper aspects of each other and regularly check in with each other emotionally. Asking your partner deep relationship questions can help shed light on their perspective on the relationship, the emotions they’ve been experiencing lately and reveal new dimensions to your partner you may have not recognized before.

A principal contributing factor to conflict in a relationship is an unhealthy or underactive communication dynamic. By finding deep questions to ask your long-term partner, you can not only create a more open and collaborative platform for exploring your respective issues, but you also set up a pattern in your relationship where disclosure is welcomed instead of being a source of unease.

Like with friends and family, you can ask your partner deep questions regularly or even use these questions as a structured exercise to help you grow closer and more intimate. Remember that it’s not just about the right questions but how you follow up. Try one of these questions with your partner. 

81. What’s your biggest fear about us as a couple?
82. Do you think we communicate well?
83. What’s your favorite thing about the way we love each other?
84. What’s a challenge you think we’ll face together?
85. Do you feel supported by me in your goals?
86. What do you think we bring out in each other?
87. What’s something I do that makes you feel loved?
88. What do you think our love looks like to other people?
89. What’s one way we could grow stronger as a couple?
90. Do you feel we’re on the same page about the future?

Deep questions to ask your boyfriend

Should you be asking your boyfriend different deep questions just because he’s a guy? To a great extent, studies have shown that you should. This is because men and women approach conversation differently, sometimes using the same social strategies with completely different goals.⁴

Men are often bolder and more direct in interactions, but they sometimes do behave differently around woman partners. A study published in Men and Masculinities found that men opt for conflict avoidance in romantic relationships and are reluctant to ask questions that might negatively impact them.⁵

Approaching your boyfriend from a more neutral, fact-gathering standpoint by using a deep question instead of relationship ones allows you to encourage him to open up to you about the issues and emotions that underlie the question. You can also establish a dynamic where talking about each other’s feelings is treated with empathy and thoughtful communication.

Guys can sometimes be resistant to overly structured bonding. Try testing the waters with a few deep and meaningful questions and see how they respond. You can craft more appropriate questions from there, or use one of these.  

91. What’s something you’ve never told anyone else but would tell me?
92. What scares you most about being vulnerable?
93. Do you think love is more about choice or emotion?
94. What’s one way you want me to support you better?
95. When do you feel most confident about yourself?
96. What’s a dream you’ve had that you don’t talk about?
97. What do you think your younger self would think of who you are now?
98. What do you want us to achieve together as a couple?
99. What’s the hardest part about loving someone, in your opinion?
100. Do you think we’ve helped each other grow?

Deep questions to ask your girlfriend

Conversely, another study found that women are generally very prominent actors in relationship conflict resolution but also report feeling limited in their role due to gender and cultural norms.⁶ Finding deep questions to ask the woman you’ve been dating is as much a signal of openness and love as it is a request for information. It opens the door for them to ask you deeper questions in return. 

The question is important but the act of consistently engaging them on a deeper level and inviting them into your interior life creates a positive communication pattern. One that is founded on trust, mutual respect and authenticity. It helps you avoid conflict because issues are often addressed before they develop into bones of contention.

Women are generally more open to deep questions and discussing their emotions, so you can make these questions a daily part of your interactions. They’re also effective as an intimacy-building exercise. 

101. What makes you feel safe in a relationship?
102. What’s a way I can show you more love?
103. Do you think our relationship is helping you become who you want to be?
104. What’s your favorite thing about the way we spend time together?
105. What’s something I do that makes you smile even when you’re upset?
106. What scares you about long-term love?
107. Do you feel understood by me?
108. What’s one of your dreams I can help you chase?
109. What do you want us to always protect in our relationship?
110. Do you think we balance each other out?

Deep questions to ask someone you like

These are the kind of questions that engage the person you like in a more meaningful way, exploring aspects of their personality, their outlook on the world, and how they approach dating and relationships. These can be useful when you’re not ready to fully confess your feelings or want to broach the topic in a more subtle way that still gets the message across.

Finding the right deep questions to ask your crush isn’t as important as how and when you decide to ask them. With the right timing and tone, these questions will not only make it feel like they arose more naturally from conversation but also express a more grounded and mature outlook on emotional intimacy.

You can use these deep questions to break the ice when checking up on your crush over text or insert them into a casual interaction to steer the conversation towards more meaningful topics. You can use one of these examples directly or as inspiration.

111. What do you think makes two people truly click?
112. What’s something you’re afraid to admit about yourself?
113. Do you believe in soul-deep connections?
114. What’s the most meaningful compliment you’ve received?
115. Do you think timing matters more than chemistry?
116. What’s one thing you’re searching for in a relationship?
117. Do you think love is a feeling or an action?
118. What’s the bravest thing you’ve done in love?
119. What makes you feel most at ease with someone new?
120. Do you believe relationships change people for the better?

Deep questions to ask on a first date

You may think that deeper topics should be generally avoided on a first date until you’ve established a connection and a warmer, more distinct conversational flow. But coming up with deep questions to ask on a first date is a great way to find common ground and create that initial connection. A study in the Journal of Personality and Social Psychology found that we as humans consistently underestimate how open relative strangers are to exploring more meaningful topics rather than everyday small talk.⁷

Beyond the obvious benefits of being more interesting during a first date, deep questions often help us reveal more and feel closer to the person we’re talking to. Put yourself in their shoes. There may be quite a few interesting topics or personal stories that you’d like to share, but you know that simply inserting them awkwardly into a conversation would seem strange. Deep conversations create a natural outlet for the personal information people want to share.

Try one of the questions below during the middle and later stages of the date, when the energy between you feels more relaxed.

121. What’s something you value more than anything else?
122. Do you think first impressions are usually right?
123. What’s a life lesson you’re still learning?
124. Do you think vulnerability on the first date is good or risky?
125. What’s one thing you’re most grateful for right now?
126. Do you believe people cross paths for a reason?
127. What motivates you to get up in the morning?
128. Do you think happiness comes from within or from experiences?
129. What’s the biggest dream you’re currently chasing?
130. What do you think makes a first date unforgettable?

Deep questions to ask on a second date

On the second date you’ll likely feel more at ease with each other because you already feel a certain kind of familiar warmth and chemistry. For this reason, deep second date questions should be a little more daring. You can even start to explore topics you may have noticed they were reluctant to broach on the first date but are an important part of your dating criteria.

But it’s still important to make the questions somewhat unique and engaging because another big focal point of second dates is compatibility. Deep questions have a way of addressing both conscious and implicit compatibility. The questions themselves are designed to create a more open interaction that’s rich in personal anecdotes and emotional viewpoints. At the same time, the questions also make the conversation feel more meaningful and rewarding.

You can start asking deeper questions towards the beginning of the date, if it feels like the right time. Don’t let them interrupt an already positive conversation, though. Here are some examples you can follow to inform your questions.  

131. What’s a hidden passion you’d like to share with someone?
132. Do you think comfort or excitement matters more in relationships?
133. What’s one story from your past that shaped you deeply?
134. Do you think you’re more of a dreamer or a realist?
135. What’s something you’ve always wanted a partner to ask you?
136. What’s a value you’d never compromise in dating?
137. Do you believe second chances in love work?
138. What’s your proudest personal achievement so far?
139. How do you think people grow closer after the first impression?
140. What’s something you’ve learned from a past relationship?

Unexpected deep questions

The kinds of meaningful questions are a bit random and made to entertain someone and interact with their imagination in an unconventional way. They let you harness the power of the unexpected to pleasantly surprise your date, make them stop and really think about their answer.

While these kinds of deep questions certainly have a time and place in interactions, using them can help elevate the conversation and take it in more interesting directions. It has also been found that we neurologically enjoy positive experiences more when they’re unexpected.⁸ It has practical benefits in that unexpected questions often get us to drop our boundaries. This often involves either indirectly sharing personal aspects through their answer or feeling more energized and engaged by certain unexpected questions.

It’s best to be quite sparing with unexpected questions because they can often seem manufactured, but in a way that makes you seem inventive. But shaking up the conversation too often can impact its natural flow and make the questions feel awkward.

141. If you could know one truth about the world, what would it be?
142. What’s something you wish people would ask you but never do?
143. Do you think we ever really know ourselves?
144. What’s a random moment that unexpectedly changed you?
145. If you had one question answered about your future, what would it be?
146. What do you think people waste the most time on?
147. What’s a belief you once held that you no longer do?
148. Do you think happiness is a destination or a journey?
149. What do you think is the most powerful human emotion?
150. Do you believe coincidences carry meaning?

Deep personal questions

When it comes to deep life questions that are personal, it’s about expressing positive and slightly more complex interest in the things in their life that make them unique and the ideas that fuel their passions. By approaching personal details from a deeper angle, it engages the person you’re talking to on a more intellectual level, shows them that you’re open to learning more about them and indicates that, regardless of their answer, they won’t be judged. 

When you’re constructing different deep questions to ask about their life that venture into more personal territory, it’s always a good idea to start slow. Ask them something only lightly personal to begin with and if you can see it’s a topic that excites them, start going slightly deeper with your follow-up questions. You need to leave room for them to ask you personal questions in return or they may end up feeling like they’re under the spotlight for too much of the interaction.

Let these examples give you insights into the right tone to strike with your personal and life questions. 

151. What’s the hardest secret you’ve kept?
152. Do you find it easy or hard to forgive yourself?
153. What’s a decision you regret but learned from?
154. What part of yourself are you most proud of?
155. What’s a moment you’ll never forget because it changed you?
156. What’s a weakness you’re actively working on?
157. Do you think you’re more introverted or extroverted deep down?
158. What’s a dream you’ve kept private?
159. What do you want people to remember about you most?
160. What’s the most vulnerable thing you’ve ever shared with someone?

Deep questions about life

These are a lot like personal questions, except instead of asking the person you’re interacting with about how they live, you’re instead exploring how they think. Deep life questions can be quite broad  – such as asking about the personal philosophies that guide them – or highly tailored to the person you’re talking to and their personality – like asking about certain experiences they’ve mentioned and what they drew from them.

Life in general is often an easier topic to discuss than one’s personal life because it doesn’t require as much sharing and vulnerability. But one’s outlook on life speaks just as much to who a person really is inside as their personal experiences. This doesn’t make it a sneaky way to get around boundaries but rather represents a more appropriate and nuanced way of interacting without someone personally, but in a way that they feel more in control of.

Try a few of these deep questions when you’re already exploring more meaningful topics and want to gently shift the focus to their views on life.    

161. What’s your personal definition of a meaningful life?
162. Do you think balance in life is possible or overrated?
163. What do you think is humanity’s biggest challenge right now?
164. What’s a philosophy you try to live by?
165. Do you think pain is necessary for growth?
166. What do you think is the biggest illusion in life?
167. What gives you hope when things feel dark?
168. Do you think people are shaped more by choice or circumstance?
169. What’s something you think everyone should experience once?
170. What do you want your legacy to be?

Deep questions about love

Exploring the topics of love through deep questions is an approachable and highly relatable topic that you can share on a deep level, whether you’re a basic acquaintance or have been in each other’s lives for years. These questions explore how they approach love, their past experiences with it and how important they find the notion to be in their existence.

Finding some deep questions to ask them about love helps more than simply unpacking their attitude towards emotions and relationships. It can also be a positive signal that you’ve related the concept of love and them, in your mind. So, it almost serves as a more cerebral kind of flirting, if your relationship has that dynamic.

But it can also just be a platonic way to find common ground and grow closer to one of your friends. Try shaping one of these questions to your audience, based on the effect you want it to have.

171. What do you think love means beyond attraction?
172. Do you think love should feel easy or take effort?
173. What’s the most beautiful act of love you’ve witnessed?
174. Do you believe love can last forever?
175. What’s your love language, and how do you show it?
176. What scares you about love?
177. What’s something you’ve learned from heartbreak?
178. Do you think we fall in love once or many times?
179. What do you think is the hardest part of loving someone?
180. What’s the purest expression of love you’ve experienced?

Deep thought provoking questions

These are those enquiries into life and the self that are both highly compelling and distinct. Deep thought-provoking questions are somewhat like unexpected ones, except that they capitalize on the social aspect of engaging someone’s intellect in an unconventional way, inviting them to be thoughtful and inventive with their answer. They’re rewarding in conversation because they gently shift the focus to the person you’re talking to in a pleasant way, essentially expressing, “I’d really enjoy hearing your thoughts on this issue.”

By making sure that some of the deep questions you ask someone are also thought-provoking, you can add a lot of energy to the conversation. This can be useful if you feel like the interaction is a bit dry or dragging.

However, it’s difficult to control where the right thought-provoking questions will take you. It’s often best to use these when you’re interested in having a longer, more intellectually complex conversation. Try one of these during a conversation to see if they’re open to discussing deeper, more intellectual topics.

181. Do you think destiny is real or do we create our own paths?
182. What’s a moral dilemma you’ve struggled with?
183. Do you think people are more influenced by hope or fear?
184. What’s a paradox of life that fascinates you?
185. Do you think freedom and security can coexist fully?
186. What’s one thing you’d change about the way society works?
187. Do you think we have more control over life than we admit?
188. What’s the purpose of suffering in human growth?
189. What’s a philosophical idea you strongly connect with?
190. If you had to sacrifice a universally accepted truth for a universally experienced sense of meaning, which would you choose, and why?

Deep questions to ask your ex

People often want to reconnect with an ex. You may be looking to reflect on the relationship now that you’ve got some emotional distance from it, bring up the idea of perhaps getting back together if things change or you may just want to check in because you miss them on a friendship level.

Come up with deep questions to ask your ex that appropriately address your intentions can help you break the ice and start the interaction off on a positive and constructive note. Depending on how you separated, there may still be lingering resentment. These questions should be designed to start from a very neutral standpoint that isn’t trying to assign blame or create an argument but rather, give you both either closure or hope for a possible reunion.

You should only ask questions that speak to the reason you got in touch. For instance, asking too much about where things went wrong might give them the impression that you’re exploring getting back together. Here are some questions that address different intentions. 

191. What do you think we taught each other?
192. Do you think our timing was wrong, or we just weren’t right?
193. What’s something about me you never understood?
194. What do you think was the hardest part about loving me?
195. Do you think we grew apart or just stopped trying?
196. What’s a memory you’ll always keep from us?
197. Do you think we helped each other grow, even in small ways?
198. What do you think closure really means for us?
199. What’s something you wish you’d told me before we broke up?
200. Do you think we could have lasted under different circumstances?

Deep questions to ask yourself

Introspective deep questions are when you approach your inner dialogue and the emotions that interact with it in a very structured way. As we touched on earlier, introspection does have its limitations in terms of its mental health benefits. But this is if you over rely on it and don’t use other therapeutic tools, like gaining an outside perspective. Even studies have found that introspection is an invaluable method of addressing any lingering life or emotional issues. It’s how you first recognize the aspect of your life and thoughts that are impeding a healthy mental state. Therapists and other mental health professionals often simply give you the tools to approach self-analysis in a way that’s constructive and leads to constructive insights.⁹

You should include self-analysis in your daily routine, putting aside 10-20 minutes to unpack the events of the day and how they made you feel. You can use the insights to set up achievable goals and come up with different strategies to approach the most pressing issues in your life.  

201. What do I truly want, beyond what people expect of me?
202. Am I living in alignment with my values?
203. What am I most afraid of admitting to myself?
204. What brings me the most peace?
205. Do I let fear stop me from pursuing dreams?
206. What’s the story I tell myself that holds me back?
207. Do I spend enough time with people who lift me up?
208. What am I most grateful for right now?
209. Am I proud of who I’m becoming?
210. What do I want my life to look like in 5 years?

Deep questions for online dating

Online dating interactions are built on asking the right kinds of questions. They’re often what carry the interaction forward, particularly when you’re first connected. A good set of deep dating app questions should always form part of your approach on these platforms, particularly if you’re looking for a more meaningful connection.

They’re useful for quickly finding common ground to build more personalized questions around. They also tell the other person that you have a distinct interest in them beyond their profile picture. That you’re open to having a deeper, more authentic interaction that isn’t just dry introductory questions and half-hearted flirting.

The deep questions you ask on dating apps should be mixed in with other types, like getting-to-know-you questions, flirty questions, and even funny ones. This will highlight that you’re a well-rounded person and give them an idea of how vibrant the conversation would be on your first date. Try out one of these questions next time you’re connected and you’ll see the difference it can make to these interactions.

211. What’s something meaningful you’re looking for beyond surface-level dating?
212. Do you think online connections can be as deep as in-person ones?
213. What makes you swipe right on someone?
214. Do you think timing is important in meeting the right person online?
215. What’s your biggest hope for finding someone here?
216. Do you think it’s possible to fall in love without meeting in person first?
217. What do you think is the hardest part of dating online?
218. Do you believe sharing vulnerabilities early builds stronger connections?
219. What’s something you’d like to experience with a partner you meet online?
220. Do you think honesty is more important online than in real life?

There’s more to getting closer to someone than just asking questions. Here’s how to build on deep questions.

• Don’t ask them too many questions if they aren’t reciprocating. Questions should ideally go both ways or the interaction will start to feel one-sided.
• Be authentic with them. This will naturally make the questions you ask feel more sincere. And at the end of the day, they should accept and appreciate the real you if you want the relationship to develop.
• Always start off with more casual deep questions initially to gain rapport and get the conversation going. For instance, “What does your perfect Sunday look like?”
• When they answer, listen actively so that you can take the information on board. This won’t just help you with follow-up questions but also make future questions more suited to their personality and communication style.
• Be vulnerable with them first to show openness and sincerity. This will help them trust you more with their deeper thoughts.

What makes a question deep?

A question can be considered deep when it addresses not just a topic but the concepts and emotions that form the basis of that topic. They are very much like the other things you ask to get to know someone, except that they create depth through genuine interest and complex enquiry.  

A good way to judge the depth of a question is to look at whether it leads to emotional vulnerability and a deep conversation. A study published in Heliyon found that people tend to judge the quality of a conversation by how much was exchanged rather than the topic discussed.¹⁰

There are simple ways to make even small talk seem deeper and less mundane. For instance, on top of asking them how many siblings they have, ask about their favorite memories with their siblings or explore their family dynamics.

How to ask deep questions?

In general, communication is an essential part of any healthy, functioning relationship. So, keep these aspects in mind when trying to pose a deep question successfully.

• Always make questions open-ended when going deep so that they leave room for the other person to elaborate and share more.
• Focus less on experiences and more on how those experiences made them feel. For instance, instead of asking how someone’s holiday was, ask them what their favorite part of the trip was.
• Pay attention to their tone and body language when discussing certain topics. This will give you an idea of which deep topics they’re open to discussing and which ones may cross a boundary.
• If they seem uncomfortable discussing their feelings, try to instead focus on their values and beliefs.
• Give cues to show that you’re present and actively listening when they answer to positively reinforce any disclosure. This can be as simple as nodding your head occasionally or verbally expressing something like, “That’s an interesting perspective.”
• Make the exchange reciprocal by also being vulnerable in your responses.

How to follow up after asking deep questions?

Asking a deep question is only the first step. For the interaction to feel meaningful and rewarding, you need to follow through with the gesture. Here’s how you can do that.

• Take a certain point they made or an interesting line of thought and simply ask them to elaborate more on that aspect.
• Ensure that follow-up questions focus on emotions and perspective rather than asking for further self-disclosure.
• If they miss a cue and answer a deep question quite shallowly, you can try following up by phrasing the questions differently. A good way to do this is to pose it as a request for advice. For example, “It sounds like you handled that problem really well. Any tips for me if I’m ever in the same situation?”
• Make follow-up questions relevant to the topic and simple, so the other person doesn’t feel like they’re being cross-examined.
• Express what you think the takeaway of their answer was and ask whether they think that summation is correct.

What are the risks of asking deep questions?

Every deep social interaction comes with some degree of risk to the harmony of that relationship. But by structuring the deep questions you ask the right way, you can easily mitigate it.

• Creating discomfort – Asking questions that are too personal or invasive can end up having the opposite social effect of making you seem socially awkward.
• Seeming deliberately obtuse – Don’t ask questions where you already have an idea what the answer will be, or the questions may come across as performative or disingenuous. This is particularly a risk with follow-up questions.
• Harming a good vibe – Deep questions tend to broach more serious topics, even when posed humorously. If you’re already having an active conversation, building rapport and making each other laugh, dropping a meaningful question can potentially diffuse that positive energy. 
• Coming across as oppositional – Phrasing a question incorrectly can make it seem like you’re on the other end of the issue they’re discussing. A good question should always convey support and understanding.

How can deep questions improve friendships?

Deep questions improve friendships because they improve interactions. On the face of it, relationships are nothing more than a string of interactions that are given meaning through deeper and deeper exchange and our perspective on the interaction in retrospect. 

A study found that deep conversation invites personal reflection and mutually explores each other’s core values, past experiences, hopes and anxieties about the future. It’s through this mechanism that intimacy is created. They tested this view by having half of the study sample have two-person interactions in a highly structured, reciprocal way, with predefined deep questions to ask. The other half was also divided into pairs but weren’t given prompts and had natural, free-form conversations. The group that had a deeper conversation reported significantly higher degrees of closeness to their conversational partner, even though the questions were predetermined and didn’t come from a place of genuine curiosity.¹¹ That’s how potent depth can be in an interaction. 

How can deep questions increase intimacy in partners?

Asking our partner deep questions expresses continued interest and curiosity. It also helps evolve our own communication style to be more curious. A study in the Journal of Personality found that being curious in a relationship was strongly linked to a host of positive adaptive traits that support bonding. These include: increased tolerance of uncertainty, emotional expressiveness, use of humor, inventive thinking and a conversational attitude that isn’t critical or defensive.¹²

The fact is that while romantic relationships can sometimes fall into an interactional rut, they never stop growing and evolving. Coming up with deep questions to ask your partner not only expresses your desire to understand them on a more meaningful level but also invites them to take an active part in improving the relationship and fostering true intimacy.

As you ask more and more meaningful questions, either in daily or as a structured bonding exercise, this deeper curiosity will come to shape how open you are with each other and your overall communication dynamic.

How can deep questions strengthen bonds within a family?

Deep questions help you communicate more healthily and strengthen your bonds with your family through authentic exchange. A recent study looked at family cohesion and found that it was determined mostly by four main factors: communication, emotional bonding, adaptability and support.¹³

The great thing about all of these factors is that finding deep questions to ask your family addresses all of them, to some degree or another. As we showed earlier, being actively curious about people’s lives makes us more inventive and socially flexible. Deeper questions can similarly improve your communication style with family, over time. 

We’ve also shown how empathy and self-disclosure are a fundamental triggering mechanism for feelings of closeness and emotional bonding, even between strangers. Lastly, asking the right deep questions expresses support for family members by giving them a platform and inviting them to vent and share their current issues with you in a more meaningful way.  

How can deep questions improve communication between coworkers?

Deep questions help you interact with your co-workers in a more empathic and purposeful way. Coworkers aren’t bonded in the same way as other relationships in your life. They tend to involve a lower degree of attachment and greater emotional distance. This is why studies have found that Social Exchange Theory (SET) is felt most prominently in professional relationships.¹⁴ SET posits that we are constantly running a cost-benefit analysis during interactions, where people try to maximize what they get out of it while keeping the risk and cost of those rewards down. In less mercenary terms, we want a fair and reciprocal exchange of respect, information, trust and support with people.

In this sense, asking a colleague deep questions adds more weight to the benefit side of the equation by making each interaction feel more pleasant, productive and inherently rewarding.¹⁵ The only cost is some vulnerability, which can feel negligible with the right rapport and a non-invasive question.  

It’s important to understand that questions aren’t a life hack for intimacy. It’s very much a conscious interaction where you’re both aware of the social gears in motion. This is why phrasing and content are so important.