150+ Deep Conversation Starters

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It’s late, the lights are dimmed, you’re a little tired, but you’re not ready for bed yet—the perfect time for a deep late-night conversation. Worried about how to get the ball rolling? Don’t be! Here we have over 100 questions that are sure to spark meaningful discussions that will help you get to know each other better and build strong emotional connections.

1. What’s the latest thing you’ve learned?
2. What legacy would you like to leave behind?
3. What experience had the biggest impact on who you are today?
4. If you could live in any fictional world, where would you live?
5. If you only had 1 year to live, what would you do differently?

1. 

   Set the stage for emotional intimacy and connection. Ideally, choose a quiet, comfortable place where you can socialize with minimal disturbance or distractions. Soft, low light is great. You can also play some soft music in the background—just make sure it’s quiet enough that neither of you feel like you have to talk about it.[3]

   • It’s also best if you sit close to the person you’re talking to—you can reach out and touch their hand while you listen. Plus, you’re likely to feel psychologically closer if you’re physically close to each other.
   • Approach the conversation with a sense of curiosity. It can help add some fun to it and make it like a game! For example, you can take turns asking each other questions from this article.

2. Ask open-ended questions that allow elaboration. A question that can be answered with a single word will not be the easiest way to start a conversation. Better questions require the person to tell a story in the answer to discuss a big topic on a deeper level. When you ask open-ended questions, you’re also sending a subtle signal to the other person that you’re genuinely interested in whatever’s on their mind—you want to go beneath the surface.[4]

   • You can even turn a yes/no question into an open-ended question by adding an “and why” at the end—although these aren’t always the most interesting questions, they can still get someone talking!

3. Actively listen and ask for clarification when needed. Research shows that people feel more emotionally connected to each other when they are both present and aware during a conversation. When you actively listen, you prioritize what the other person is saying over what you might say next. Also make sure you understand what they meant before you respond.[5]

   • Remove any distractions and make eye contact throughout the conversation – this helps build emotional intimacy between the two of you.[6]
   • Give the other person your undivided attention to show them you value them and believe they are worth spending time with.
   • If you don’t understand something the other person said, asking for clarification lets them know you think it’s important to understand exactly what they’re saying.
   • The easiest way to make sure you understood someone correctly is to repeat what they said using their own words. It also gives you some time to think of your answer (assuming you got them right).

4. Share stories about yourself openly and honestly. People are often afraid of what will happen if they share something sensitive about themselves, but research shows that people are quite receptive. If you share something meaningful, most people will try to share something meaningful in return and continue the conversation.[7]

   • Don’t be afraid to admit if you are uncomfortable with an answer or if you need some time to formulate your answer before answering the question.
   • At the same time, if you feel uncomfortable answering anything, let the person know! Emotional intimacy can be difficult, and you may face some walls you didn’t realize you had—and that’s okay![8]

5. Sympathize and validate the other person’s feelings. Remember that even if you don’t agree with what someone says, their emotions are still valid. When you want to empathize with someone, focus on how they feel, not how they react as a result of those feelings.[9]

   • Acknowledge the person’s feelings and give them space to process the emotions that have come up, if they need to. You can even thank them for feeling safe enough to tell you.
   • For example, if your friend is talking about something he did as a child that he regrets, you might say, “You must have been terrified! It’s understandable that you would act the way you did—I’m sure a lot of people would do the same. you are very brave for facing it.”

6. Use follow-up questions for better understanding. The key to keeping the conversation going is to listen to what the other person is saying and find something in what they said to ask. If you can’t pinpoint anything specific that feels natural to expand on, try asking them how it made them feel or what happened next (whatever makes sense given what they said).[10]

   • For example, if a friend talks about their childhood and mentions that they watched cartoons with their dad on Saturday mornings, you can ask them what their dad’s favorite cartoon is.
   • If they are recounting a memory, you can ask them how they felt at the time or how they feel now thinking about it.

Categories: How to
Source: HIS Education