Conversation

30 Questions to Get the Conversation Going

In her book, Captivate: The Science of Succeeding with People, Vanessa Van Edwards, separates conversation into three categories based on how long you’ve spent with someone: five minutes, five hours, or five days.

I believe everyone opens up at their own pace, so I categorize interactions into small talk, ice breakers, and connection builders with each one digging a little deeper to get to know the other person better.

Below, I’ve compiled ten sample questions for each section. 

Conversation is a delicate dance of leading and following. It’s a matter of giving and receiving information. There’s an art to being vulnerable and asking probing questions without crossing a boundary or oversharing.

If you’re going to ask about deal breakers, be cautious in how you do so. You don’t want to give off negative energy.

For example, don’t ask your date who she voted for or to which political party she subscribes. At the same time, don’t announce those things about yourself. It’s too direct and very off-putting. Instead, focus on sharing your core values and learning about hers.

If your values align, the rest will follow. 

Start Small

If you’re an introvert like me, small talk probably isn’t your area of expertise. Unfortunately, it’s a highly-valued social skill in our society. So, I find it helpful to have a few open-ended questions on hand, to get the other person talking and let them dominate the conversation.

This allows me and my anxiety a break so I can do what I do best—listen. 

  1. Have you read anything interesting lately?
  2. Do you belong to any organizations?
  3. Who is your celebrity crush?
  4. What is an average day like for you?
  5. Do you do any volunteerism or charitable work?
  6. What is your favorite/dream travel destination?
  7. Tell me about the best and worst parts of your day.
  8. When you visit your hometown, what is the one place you have to stop at?
  9. Do you have any pet peeves?
  10. What does your ideal weekend look like?

Small talk doesn’t have to be meaningless chatter about the weather. You can use it to really get to know someone on a deeper level if you ask purpose-driven questions and practice active listening.

For instance, by asking someone how they would spend their ideal weekend, you can discern things like:

  • Are they a morning person or a night person?
  • Do they prefer their alone time or group settings?
  • Are they an introvert or an extrovert?
  • What are their hobbies?
  • How do they like to spend their free time?

That doesn’t even include all of the inferences you can make from their non-verbal communication. And you didn’t have to barrage them with rapid fire questions. Also, be prepared to answer any question you ask in return.

Ice Breakers

I would advise you to limit yourself to one or two of these types of questions per date. They can range anywhere from whimsical to philanthropic, but one common thread is that they’re complex questions that require critical thinking.

These are those bizarre questions you see on interview lists like—What animal most closely describes your personality?

One question is fun, two is deep, three is just plain exhausting. They’re great questions, but like many great things, require moderation to be most enjoyable. 

  1. What skill or talent have you always wanted to master?
  2. Who is the most fascinating person you’ve ever met?
  3. Would you rather have the ability to speak any language or speak to animals?
  4. If you could pick a superpower, what would it be?
  5. Would you rather take several weekend getaways or one extravagant vacation?
  6. What do you do that other people think is annoying?
  7. Do you have any guilty pleasures?
  8. What is your most irrational fear?
  9. If you could solve one global crisis what would it be?
  10. What is the best gift you’ve ever given or received?

Connection Builders

These are deeper questions that can help you really get to know your date on a more intimate-level.

  1. What is your favorite book of all time?
  2. Tell me about your best friend.
  3. What do you want to accomplish in your lifetime?
  4. Are you close with your family?
  5. What do you love most about your work?
  6. Do you have any side-hustles or passion projects?
  7. How do you want your legacy to be remembered?
  8. What is the one thing that will put you in a good mood, no matter what?
  9. Who is the most influential person in your life?
  10. What is your primary Love Language?

Use your best judgement: if it’s your first date and you’re really hitting it off, these are pretty safe topics. However, if she’s not keen to open up, if her body language is closed off, if she’s giving you short answers—my advice is to stick to lighter topics of conversation until she’s more comfortable.

If your date is slow to open up in conversation, don’t write her off or hold that against her. You never know what she’s experienced in her past. Putting yourself back out there can be difficult. Again, if you share similar values, it’s likely a good match. Just be patient and give it time.