273 Questions to ask to get to know someone beyond the surface level

If you’re here, chances are you’re looking for the best questions to ask to get to know someone new. Getting to know you questions are one of the best ways to break the ice, spark real conversations, and open the door to something deeper.

However, you need to know that it is not just about asking questions, it’s about asking the “right” ones. At the early stage of getting to know someone, keep the deeper questions for later and start with asking lighthearted, non-intrusive questions. These are the things to ask someone to get to know them that make the other person feel comfortable enough to show more of their personality, share their values, and open up about their backgrounds. From there, you can decide if you’re compatible enough to go into deeper conversations. As eharmony relationship expert Laurel House puts it, “The more you ask, the more you know, the more you grow—together or apart”.

Without a doubt, we know that asking questions to someone you have just met can be harder than it sounds (social anxiety can kick in). That’s why we’ve put together a list of questions to get to know someone in various categories, e.g., from fun questions to questions about hobbies and interests to self-reflection and even deeper questions. With these questions, you’ll always have things to ask to keep the conversation flowing.

Best questions to ask to get to know someone

Knowing which questions to ask can make all the difference. Experts emphasize that thoughtful inquiries about core values, lifestyles, and love languages can help you uncover compatibility early on and set the foundation for a healthy relationship. That’s why relationship expert Laurel House recommends the following questions to ask:

1. “What’s your dating purpose? What are you looking for and why? Do you want to get married? Do you want to have children? It’s essential that you find out if you are on the same dating purpose. Because if you don’t find out this essential information early on, you might connect with them, form an attachment, and then find out that you have different dating purposes and you have to break up. It’s better to reveal the essential must-haves and can’t-stands early on.
2. What does your lifestyle look like? Your average day, week, month? You want to know if your daily lifestyles align and if your lives can fuse together.
3. Are you an introvert or an extrovert? Are you a homebody or adventurer? This reveals if you prefer to be out with others or at home alone. How you choose to experience life is important when you are exploring the possibility of experiencing life together.
4. What is your work/life balance? And how do you like to travel? What your work life, relaxation life, and vacation life look like is another way to communicate what your life looks like and if your lives can align.
5. What makes you feel loved? What is your Love Language – Quality time, Physical Touch, Gifts, Words of Affirmation, Acts of Service, or the two additional languages that eharmony has developed: Shared Activities and Feeling Seen. More than what your love language is, how your love language is experienced is important to share. You are essentially giving your potential partner a road map to make you feel the essential 3S’s (Safe, Sexy, and Seen) in order to create the feeling of care and eventually love. People naturally give care and love in the way that they experience care and love. So, if two people have different love languages, they might not feel cared for or loved by the other because the other is giving care and love in the way that they feel cared for and loved and not the way that the other person experiences feeling cared for and loved.”

Questions to ask to get to know someone deeply

When getting to know someone on a deeper level, it is only right to ask questions that are in-depth and intentional. You wouldn’t want to ask “what’s your nail polish color” in moments like this. Carefully pick deep questions that would lead to a heart-to-heart conversation. And when asking questions like this, ensure your focus is 100% on the person, let them feel heard and seen. This alone is enough to leave a lasting impression and get them thinking about you. And who knows? A love story might just be brewing. So, let’s help you with some deep questions to ask:

1. What’s your biggest hope for your future?
2. How do you usually show love to the people you care about?
3. What experience shaped you the most?
4. Do you believe people meet for a reason?
5. What’s something you fear losing?
6. What’s your definition of true intimacy?
7. How do you usually process disappointment or failure?
8. What part of yourself are you most proud of?
9. What’s a dream you’ve kept secret until now?
10. Do you think love is more about passion, commitment, or both?
11. What does “home” feel like to you?
12. When do you feel most at peace?
13. What do you think makes two people truly compatible?

Basic questions to get to know someone

Let’s say that you connected with someone and you guys matched each other’s energy right away. Both of you have probably passed the small talk phase and you feel a deeper connection starting to build up, then here is where the basic question comes in. These are one of the first important sets of questions that are good to ask when building a relationship. Basic questions are not supposed to be intense, so you don’t have to be nervous when asking. They are just one of the necessary conversations to have, so you and the other person get to know each other beyond a surface level.  We have a list of engaging basic questions you’ll find useful:

14. Where did you grow up?
15. Do you have siblings?
16. What’s your favorite food you could eat every week?
17. Do you like mornings or evenings better?
18. What’s your go-to comfort show or movie?
19. Do you enjoy cooking or prefer eating out?
20. Are you more of a tea or coffee person?
21. Do you enjoy surprises?
22. What was your favorite subject in school?
23. Do you like pets? If yes, cats, dogs, or something else?
24. Do you enjoy trying new things, or do you prefer familiar routines?

Good questions to ask to get to know someone

To be able to establish a relationship with someone, you must ask certain questions or have conversations that make them comfortable enough to share and see you as a safe space. These questions are good for any level of relationship you intend to have so make them casual but at least exciting. As casual as they can be, they actually do give room for deeper bonds. And from there, the person loosens up to you and further conversation about other things can be had. To make it easier for you, we’ve collated some good questions to help you get to know someone better:

25. What do you look forward to the most in a typical week?
26. What does a relaxing weekend look like to you?
27. Do you prefer city vacations or nature escapes?
28. What’s your favorite way to celebrate small wins?
29. Do you usually make plans or go with the flow?
30. How do you usually spend holidays?
31. What’s a habit that makes your day better?
32. Do you enjoy trying new cuisines when you travel?
33. Who has been the biggest influence in your life so far?
34. What’s something you’d like to learn or get better at?

Questions to ask a guy to get to know him deeper

Just like every other person who wants to feel seen, a guy also wants to feel heard and loved. So when coming up with questions to ask a guy, go for open-ended topics that would encourage him to go into more details about himself. Aim for questions that ask more about his core values and past experiences, pay attention to his response, and this way you are on the right path to building a healthy bond with him. Study shows that men tend to be attracted to women who are aware of their feelings and listen to them. So, we’ve helped you with some good open-ended questions to ask like:

35. What kind of challenges motivate you?
36. Do you usually trust your instincts or logic more?
37. What kind of partner do you hope to be?
38. Who do you admire as a role model, and why?
39. Do you find it easy or hard to open up about your feelings?
40. What’s the best advice you’ve ever received?
41. Do you see yourself as more of a planner or a risk-taker?
42. What keeps you grounded when life gets busy?
43. What’s one thing you’re currently working on improving in yourself?
44. Do you think love should feel easy, or does effort make it meaningful?
45. What’s a dream you’ve never told many people about?
46. How do you like to celebrate personal milestones?

Questions to ask a girl to know her better

It’s time to ask a girl questions to get to know her better, but you aren’t too sure of what to ask. You want to make sure that the questions are respectful and comfortable to ask and engage her. Don’t worry because we compiled a list of questions to ask a girl that we think will help you have a great conversation. Keep in mind that if she isn’t excited to answer personal questions or is hesitant when you ask them, don’t push for more answers. Instead, learn to read her body language and if you get a negative reaction, put an end to the conversation. Else, here are some ideas for questions to ask a girl:

47. What qualities make you feel most respected in a relationship?
48. Do you feel more energized around people or when you have alone time?
49. Who inspires you most in your daily life?
50. What’s something you’re really passionate about?
51. How do you usually handle stress?
52. What do you value most in friendships?
53. What’s your favorite kind of date — cozy or adventurous?
54. What’s something that always puts you in a good mood?
55. Do you like surprises, or do you prefer knowing plans in advance?
56. What’s one thing you’d love to try at least once?
57. What’s your proudest accomplishment so far?
58. Do you think you’re more of a dreamer or a realist?

Personal questions to ask to get to know someone

Asking personal questions is important, but you should first reach a level of mutual energy in the relationship before bringing them up. By energy, we mean you both have spent time texting, calling, and getting to know yourselves to a certain extent enough to start asking such questions. It’s also good to remember that sharing goes both ways, you should also be vulnerable so that the other person doesn’t feel alone in the conversation. You wouldn’t want it to seem like an interrogation, so make sure to bond on experiences. Plus, a good conversation requires one person to listen attentively while the other speaks. So don’t interrupt while they are speaking. Here are some ideas:

59. What’s your happiest memory from the past year?
60. Do you believe people can really change?
61. What’s something you wish people asked you more often?
62. How do you usually make big decisions?
63. What do you want people to remember about you?
64. What’s a life lesson that stuck with you?
65. What kind of family traditions mean the most to you?
66. What do you find most attractive in a partner, beyond looks?
67. How do you like to spend your birthdays?
68. Do you think of yourself as more future-focused or present-focused?

Fun questions are a great way to gauge someone’s sense of humor. Their response shows you if you both find the same things funny, or if you can make a joke and they laugh along instead of taking it the wrong way. According to ResearchGate, using humor in conversations with a partner was found to boost positive emotions.¹ The findings suggest that both people in the relationship, the one making the jokes and the one enjoying them, experience emotional benefits when humor is brought into their interactions. Now that you know this, it’s time to start asking some fun get to know you questions that would have the other person laughing so hard. Here’s a list of funny questions to ask that you can select from:

1. What are three random things that first come to your mind?
2. What’s your best dad joke?
3. What’s the weirdest thing you have ever eaten?
4. What’s the most embarrassing item of clothing you have ever worn?
5. What’s the weirdest thing you’ve ever Googled?
6. Would you rather be bald or have a mullet?
7. Would you rather be trapped in a room filled with snakes or spiders?
8. Do you have a completely useless talent? What is it?
9. What’s your favorite song to sing in the shower?
10. What’s the oddest dream you’ve ever had?

Unpredictable questions to ask someone to get to know them

It can be helpful to ask a date random questions to get to know someone deeply. Those types of questions the other person doesn’t expect. The good part of it is that they are not personal or have much depth to them (could even be hilarious), so you can ask at any point in your relationship. They also don’t have to be planned, they can just come out of nowhere, but as random as they are, they also give you insight into how the person naturally thinks and the perspective they see things from. These are unpredictable questions you can ask someone without having to stress about coming up with any:

1. If you could instantly master one skill, what would it be?
2. What’s a totally random fact you love?
3. If you had to eat one meal for a year, what would it be?
4. Would you rather live by the ocean or in the mountains?
5. If your life had a theme song, what would it be?
6. What’s the most adventurous thing you’ve done on a whim?
7. If you could trade lives with someone for a day, who would it be?
8. Do you think you’d survive a zombie apocalypse?
9. What’s the most unusual compliment you’ve ever received?
10. If you were a character in a movie, what role would you play?

Intriguing Questions to ask to get to know someone

Maybe you want to skip the small talk and be vulnerable to get to know someone— if so, ask intriguing questions. These unusual questions are fun and perfect for sparking conversations that can lead to unexpected insights about what makes the other person tick. They’re also a great way to discover new sides of someone, as they encourage people to express the daring and bold aspects of themselves that they don’t usually get asked about. For example, not many people get asked, “What do you think is your most underrated strength?” Asking this not only stands out but also makes them feel good that someone genuinely cares to know. Here are some interesting questions to ask someone:

11. What’s something you’ve always wanted to do but haven’t yet?
12. What’s the most meaningful gift you’ve ever received?
13. Do you think dreams have hidden meanings?
14. What’s a moment that changed the way you see life?
15. Do you think people are born with purpose or create it themselves?
16. If you could relive one day in your life, which one would you choose?
17. What’s something you think most people misunderstand about you?
18. Do you believe in fate, coincidence, or choice?
19. What do you think is your most underrated strength?
20. If you had a chance to live in another time period, would you take it?

Unique Questions to Get to Know Someone

Everyone has something that makes them unique and stand out from others. It could be a unique ideology, personality, fashion sense, or even something as simple as a go-to food choice. Asking someone questions about this can make them open up more easily because it shows you’re genuinely interested in what sets them apart. And when they share what inspires them, don’t judge (what makes them unique may be different from what you usually like), but that’s the beauty of it. Judging would only push them away. Instead, hype them up and even show interest by saying you’d love to embrace that style too. That’s a great way to bond more deeply. Here are some ideas for unique questions to ask:

21. If happiness were a currency, what would make you rich?
22. What fictional world would you most like to live in?
23. If you could instantly learn another language, which one and why?
24. What’s the oddest job you’ve ever thought would be fun?
25. Do you prefer to plan the journey or enjoy the destination?
26. If you had a personal mascot, what would it be?
27. What’s a food combo you love that others find weird?
28. If your younger self met you today, what would they say?
29. What do you think makes people truly magnetic?
30. If you could time-travel only once, would you go forward or back?

21 Questions to get to know someone

Getting to know someone new is so exciting, especially when it’s your long-time crush. But while the butterflies are dancing in your belly, somehow, all the questions vanish from your head. Don’t worry, we’ve all been there. That’s why our classic go-to 21 Questions Game comes in. This is the perfect icebreaker to help you have any conversations without the awkward silence. So, take a deep breath, walk up to them, and once you can tell they’re vibing with the conversation, you can ask them any of the 21 questions we’ve put together for you. Here’s the extensive list of good get-to-know-you questions to help spark meaningful conversations:

31. What’s one thing people are often surprised to learn about you?
32. Do you believe in love at first sight?
33. What’s your favorite childhood memory?
34. Do you prefer mornings or late nights?
35. What’s your idea of fun on a Saturday?
36. Do you believe in soulmates?
37. What’s your favorite book or movie character?
38. What’s a personal challenge you’re proud of overcoming?
39. Would you rather always be hot or always be cold?
40. What’s your guilty-pleasure song?
41. Do you think opposites attract in relationships?
42. What’s your favorite holiday tradition?
43. What motivates you when you’re tired?
44. If you could relive one year of your life, which would it be?
45. Do you prefer texting or calling?
46. What’s the best trip you’ve taken so far?
47. Who do you go to for advice?
48. What’s your definition of happiness?
49. Do you like surprises?
50. If you had a warning label, what would it say?
51. What’s something on your bucket list you hope to do soon?

Questions to Get to Know Your Partner Fully

Do you know that in a relationship, you can never fully know your partner?. Let’s be honest, there’s so much more to a relationship than “I love you”. The truth is without communication, those sweet assuring words can feel empty. That’s why you’ll always hear that communication is the key to a successful relationship. So how do you communicate? By asking deep questions that reveal more sides of them. Here’s a quick tip: if you notice your partner isn’t being genuine or is holding back, you might need to pause, reflect, and gently call it out before moving forward. We recommend asking these relationship questions, so you are on the right path to knowing your partner better.

52. What’s your favorite thing about how we spend time together?
53. What habits of mine do you secretly appreciate?
54. What’s something you’d love for us to try as a couple?
55. What’s your biggest dream for our future together?
56. Do you think we balance each other well? How so?
57. How do you feel most supported by me?
58. What was your first impression of me?
59. What small things make you feel loved daily?
60. What’s something you want us to keep doing as we grow together?
61. What do you admire most about our relationship?
62. What’s something we could work on as a team?
63. Do you feel we challenge each other in healthy ways?
64. What does “home” mean to you?

Questions to get to know someone through online dating

According to Pew Research, over 10% of partnered adults, whether married or in a committed relationship, met their partners through online dating platforms.²  eharmony itself has helped singles build lasting relationships. So, if you have someone you met on a dating app and you matched each other, then clearly, asking the right question can help you build a solid love story. Before asking the question, ensure that they are also on the same page as you, and that you can ask these questions smoothly without making them feel you are coming off strong. Try asking some of these dating app questions we highly recommend:

65. What made you like my profile?
66. What’s your favorite way to spend a lazy Sunday?
67. Do you enjoy cooking, or do you prefer takeout?
68. What’s the best concert or event you’ve been to?
69. Do you like planning trips or going with the flow?
70. What’s a hobby you’d love to share with a partner?
71. What’s your favorite way to relax after a long day?
72. Are you more of a “stay in and chill” or “go out and explore” person?
73. Do you enjoy meeting new people, or do you prefer smaller circles?
74. What’s a fun fact about you that’s not on your profile?
75. What’s the best date idea you’ve ever had in mind?

Good questions to ask to learn more about their expectations

Being clear about your and the other person’s expectations right from the start is the best way to have a functional, healthy relationship. It can also help you sidestep the heartbreak that’s inevitable when you and your partner just aren’t on the same page.

76. What does a balanced relationship look like to you?
77. What are your goals in a relationship?
78. How do you like to receive affection?
79. What would you like to see more of in a relationship?
80. What would you like to see less of in a relationship?
81. Do you prefer staying in or going out?
82. Where do you see this relationship a year from now?
83. What can we do to make this relationship easier for each other?
84. What is your love language?
85. What’s your idea of a perfect date?

Core values questions to ask to get to know someone

Your core values in a relationship are the things that are most important to you, the principles that guide your life. Shared values are often the key to what makes a relationship work; while opposites attracting is great in theory, in reality, people are far more likely to find happiness with partners whose values match theirs. Here are some questions to figure out your partner’s core values:

86. What is important to you?
87. What do you spend your free time on?
88. What do you talk about doing but don’t actually do?
89. If you could live anywhere, where would it be?
90. In your opinion, what are the three things a person should be?
91. In your opinion, is lying ever acceptable? In what circumstances?
92. What are your political beliefs?
93. How important is religion to you?
94. Find a list of values and pick your top three. How do you define each of those values?
95. If you were in a situation that caused conflict between your most important values, how would you proceed?

Thought-provoking questions to ask people

It’s fun to laugh with your partner, but you’ll want meaningful conversations too. These ten questions will push you both to really think about the answers.

96. What keeps you up at night?
97. If you had one day left to live, what would you do?
98. If you could ask me anything and have me answer truthfully, what would it be?
99. What does love mean to you?
100. If money didn’t matter, what would you do with your time?
101. When you were a kid, what did you think being this age would be like? Is the reality different?
102. If you had unlimited confidence, what daring things would you do?
103. If you were going to transport us into any era (either forward or back), where would we go and why?
104. Who inspires you to be a better person?
105. If you could fix one of the biggest problems in the world, what would that problem be?

Questions to ask to get to know their future, ambitions, hopes, and dreams

No matter how great the present is, thinking about the future is important, too. Questions about the future let you find out if you have a common vision of what that future is and are best asked early.

106. What would you do with your life if you were suddenly awarded a billion dollars?
107. What’s one thing you want to do together that we’ve never done before?
108. Where do you see yourself in five years?
109. Do you think elderly parents should move in with their children once they can no longer live on their own?
110. What are your thoughts on having kids?
111. What does retirement look like to you?
112. What does your dream house look like?
113. Do you plan on staying in this city forever? If not, where would you like to move?
114. What are your financial goals? What steps are you taking to achieve them?
115. Do you have a bucket list? What are your favorite items on it?

Our families make us, and our childhood experiences can shape who we are as adults. Besides all of that, it’s just fun to hear stories about when they were younger. Here are some questions to ask to get to know about their past:

116. Where did you grow up?
117. Do you have siblings? Are you close to each other?
118. How often do you talk to your parents?
119. Is there anything about the way you were raised that you would like to replicate with your children?
120. Is there anything about the way you were raised that you do not want to pass on to future children?
121. Do you have a favorite family tradition? What is it?
122. What’s a childhood treat you still enjoy as an adult? Is there one you miss?
123. Were/are you close with your extended family?
124. What was your favorite activity as a child?
125. What was your favorite subject in school? Your least favorite? Why?

Questions to ask about hobbies and interests

When you think of questions to ask to get to know someone, a person’s hobbies aren’t just how they spend time, they can also be a good indicator of their values and personality. These kinds of questions work well as icebreakers, and are a good option when it comes to thinking of great first date questions. You can also ask follow-up questions if something piques your interest.

126. How do you spend your free time?
127. What’s your favorite thing to do on a rainy day?
128. Do you have a passion project?
129. What’s your favorite thing to do after work?
130. Would you rather have a quiet dinner with a few friends or a massive party with lots of people?
131. Do you think hobbies should be monetized? Why or why not?
132. Do you prefer hobbies you can do on your own, or ones you need other people for?
133. What’s the oddest hobby you’ve ever heard of?
134. Is there a hobby you pursued as a child that you’d like to take up again as an adult?
135. Would you be okay with sharing a hobby with your significant other?

Travel is a big part of some people’s lives… and something to be avoided at all costs for others. Even if you both love to see the world, you might have very different travel styles. Here are some questions to gauge if your travel habits will mesh well.

136. Do you like to go full speed ahead or are you a more relaxed kind of traveler?
137. What’s your favorite kind of destination? Cities, mountains, beaches, the countryside? Or a mix?
138. What kinds of things do you think it’s important to spend money on while traveling?
139. What’s something embarrassing that happened while you traveled?
140. Do you prefer to be the one doing the planning, or would you rather someone else do it?
141. What’s your dream destination that you haven’t visited yet?
142. What’s a popular travel destination that you think is really overrated?
143. What’s your packing style? Carry-on only or all the checked bags?
144. What kind of activities do you like to do when you travel?
145. What’s your favorite trip you’ve been on so far?

Good questions to ask to get to know someone about friends and social life

Friendships are important not only for you but for a healthy relationship as well. You also don’t want to end up with somebody whose social life is incompatible with yours, so it’s especially important to ask these questions before you get too serious.

146. Would you rather have a few close friends, or many acquaintances?
147. What is your favorite way to spend time with your friends?
148. Are you more of an extrovert or an introvert?
149. What do you value most in a friendship?
150. How often would you ideally go out every week?
151. Have you ever had a friendship breakup? What happened?
152. Do you think people with vastly different viewpoints can be friends?
153. What is your favorite thing about [Friend’s Name]?
154. What would it take for you to end a friendship?
155. What would you do if your friends didn’t like me?

Career questions to ask

Given that a large part of our lives is our jobs (as well as the whole needing money to live thing), it’s important to be aware of your partners’ stance on things like career and work-life balance. We’ve outlined some questions to ask to get to know someone about their 9 to 5:

156. If you could choose any career right now, what would it be?
157. Would you rather have a fulfilling but low-paid career, or one that paid well but wasn’t your passion?
158. What’s your favorite thing about your job?
159. How many hours do you work? Are you okay with the amount?
160. How would you feel if I made more money than you?
161. Would you be willing to stay home with the kids while I work?
162. If I had to move for work, would you be willing to move with me?
163. What are your long-term career goals?
164. How do you think your work-life balance will change once kids are in the picture?
165. What do you see yourself doing after retirement?

It is incredibly important to know yourself, as self-awareness leads to making better life choices. Introspection isn’t always easy, however. You and your partner can help each other through the process, using these questions as a guide.

166. Am I using my time wisely?
167. Is there anything I’m taking for granted?
168. Are my actions in line with my values?
169. Am I allowing things out of my control to control me?
170. What am I most scared of?
171. When did I last try and step out of my comfort zone?
172. What is worse: failing, or never trying?
173. What am I most grateful for?
174. What would I like to change about myself?
175. If today were my last day, would I be satisfied with my life?

Books, movies, games, and other media questions to ask to get to know someone

For most of us, books, movies, and other media are how we relax – and how we connect with other people. Some questions to ask that will get the ball rolling are:

176. What is your favorite book? Why?
177. Do you think movie adaptations are ever as good as the original book?
178. What’s a book or movie that everyone loves but you don’t?
179. If you could change the ending to any book, movie, or TV show, would you? How would you change it?
180. Have you re–read any of your childhood favorites recently? Did you love it as much?
181. Would you rather read a physical book, use a Kindle, or listen to an audiobook?
182. Would you rather binge a TV show all at once, or watch new episodes once a week?
183. Do you like video games? How do you play – on your phone, a console, or your computer?
184. Would you rather go to the theater or watch a movie at home?
185. Which movie have you seen in the theater that remains unforgettable for you?

Questions to ask about likes, dislikes, and pet peeves

Everyone’s got them – likes, dislikes, and those irrational pet peeves that make no sense to anyone else, but are a great conversation topic.

186. What’s something you like that most people don’t?
187. Conversely, what’s something you dislike that most people are a fan of?
188. Do you have any pet peeves? What are they?
189. Do you think it’s important for partners to share the same likes and dislikes?
190. If someone has a habit you dislike, how do you deal with it?
191. How comfortable are you with awkward conversations?
192. Are there any societal norms you think are stupid?
193. What would you like to spend more time doing?
194. What is something you wish fewer people did?
195. What is your ideal day like?

Tips for selecting good questions to start conversations

When wanting to date online, one of the first things to learn is how to start a conversation on a dating app. Then after you’ve chosen the right questions to ask, it’s important to also think about how to ask someone out to make the conversation enjoyable and meaningful. Remembering the way you select and ask these questions can significantly impact the experience for both of you, helping to foster a genuine connection and ease any nerves. We summarized some of the most important tips to keep in mind:

• Tip 1: When asking thought-provoking questions, especially in anxiety-inducing situations, it’s crucial to create a comfortable and welcoming environment. Start by choosing a relaxed setting where both you and the other person feel at ease – think of a cozy café, a quiet park, or any place that naturally encourages open conversation. Pay attention to the body language and signs of attraction, both yours and theirs. If you notice signs of discomfort, such as crossed arms or lack of eye contact, be ready to gently steer the conversation in a different direction. “However, it’s also important not to create a narrative that the other person isn’t interested without asking directly. Assumptions like these often stem from our own fears, and they can lead to unnecessary misunderstandings. Instead, approach with curiosity and openness — ask how they feel or what they think, rather than letting anxiety drive your interpretation. This way, you create clarity and connection, rather than feeding into self-doubt or miscommunication.”, relationship expert, Dr. Lalita Suglani adds.
• Tip 2: Pacing is key—don’t bombard the other person with questions. Allow time for them to respond fully and avoid rushing the conversation. This not only shows respect, but also gives both of you the chance to explore the topic more deeply.
• Tip 3: Active listening is just as important as the questions themselves. Engage with their responses by maintaining eye contact, nodding and offering thoughtful follow-up questions. This demonstrates genuine interest and helps keep the conversation going naturally, deepening the connection between you.
• Tip 4: Share a bit about yourself, too. Conversations are a two-way street, and offering some insight into your own thoughts and experiences can encourage the other person to open up as well. It helps to build trust and makes the dialogue feel more balanced and reciprocal. Relationship expert Laurel House states: “The key is to lean in. Answer the questions unapologetically, confidently vulnerably, and without fear of judgment. Once you have answered the questions – being the example of your expectation, you ask the same questions of them. Look at conversations as opportunities to explore – yourself and them. These questions can help you to get clear on who you are, what you need, what you dream, and how you connect with others. Don’t afraid to go deep, get raw, and have fun.”
• Tip 5: Lastly, approach the interaction with an open mind and a sense of curiosity. Be flexible and ready to adapt to the flow of the conversation, enjoying the process of getting to know someone on a deeper level. The goal is not just to gather information, but to create a shared experience that both of you can enjoy and remember fondly.

Expert Tip: Ask for the “Where” and “Why”

“Remember to extract ‘where were you, where are you, where are you going?’. By asking and answering questions from these three perspectives, you will allow for deeper understanding of who you both are, how you came to be, and what you are looking for moving forward.

And remember to ask ‘Why?’. It is the ‘why,’ not the ‘what’ that allows for understanding and connection. Because it’s not what we do, but why we do it that is truly illuminating. ‘Why’ is also where feelings lie, and that is where vulnerability lives. And it is in vulnerability that the heart opens. Daters who are communicating with an open heart, are open to feeling for each other.”

Laurel House

eharmony Relationship Expert

How to start asking the right questions and build deeper connections?

As said earlier, asking the right questions is the secret to building any meaningful relationship. People love feeling seen, heard, and understood, and the questions you ask can make that happen. Here are a few strategies for how to start asking the right questions:

• Think about what you’d really like to know about the other person.
• Keep in mind how far the relationship has progressed.
• Be clear on what you want out of the conversation.
• Make sure the setting feels relaxed and comfortable.
• Ask your questions at a natural pace.
• Listen closely to their answers.
• Open up and share about yourself, too. According to eharmony relationship expert Laurel House, “Asking questions and answering those same questions is one major way to learn about them and teach them about you”
• Stay genuinely curious.

You can also use eharmony to meet potential matches and put these tips into practice.

Is it okay to ask personal questions on a first date?

Yes, it’s completely fine to ask personal questions on a first date. But firstly, ensure they are open to answering personal questions. However, personal doesn’t have to mean going overboard. Don’t pressure them to speak on a topic they are uncomfortable with. How do you know which first date questions make them uncomfortable? Pay attention to their body language. In summary, make sure the questions you ask the person are respectful. This makes them have a good impression of you and the date.

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