Deep Conversation Starters: 30 Questions Worth Asking

Thirty minutes in, you know their favourite season, their commute and their opinion of the weather. And still you have no idea what they are like. It is a common trap: small talk is easy, so we stay in it long after it has done its job. The deep conversation starters below are built to get you out. They are open, they are kind, and none of them can be answered with a single word.

Conversation Starters That Skip the Small Talk

Good conversation starters share a pattern: they ask for a story, not a fact. "Where do you work?" gets a title. "What do people misunderstand about your job?" gets a grin, a pause and then a story.

They also assume the other person is interesting, which they are. When you ask as though you want to hear the answer, they can tell. That alone makes most people more generous than they planned to be.

Deep Questions About Life and Choices

Start here when you want to hear how someone thinks.

1. What is something you changed your mind about in the last few years?
2. What is a decision you almost did not make that turned out well?
3. Which person has shaped how you see the world most?
4. What does a good day look like for you, from start to finish?
5. What is something you used to worry about that no longer matters?
6. When do you feel most like yourself?
7. What is a risk you are glad you took?
8. What is one thing you would tell your younger self?
9. What do you think people misunderstand about your job or your hobby?
10. What would you do differently if nobody were watching?

Good Conversation Starters About Memories

Memories are safe and warm. Nobody gets defensive about a childhood smell, and the answers are as different as the people giving them.

1. What is a smell that takes you straight back to childhood?
2. What was the best day of your school years?
3. Which family tradition do you miss, or still keep?
4. What is the oldest thing you own, and where did it come from?
5. What is a small kindness from a stranger that you still remember?
6. What was your favourite place to hide as a kid?
7. Which meal tastes like home to you?
8. What is the best story your family tells about you?
9. Who was your first real friend, and what happened to them?
10. What is a memory you would relive if you could pick one?

Questions About Where You're Headed

Forward-looking questions are hopeful by nature, which makes them a good way to end a call on a high note.

1. What is something you want to learn in the next year?
2. Where do you hope to be living in five years?
3. What would you build if you had a free month and a small budget?
4. What is a goal that scares you a little, in a good way?
5. Which habit are you trying to build right now?
6. What would make this year a good one for you?
7. What is one thing you would like to be known for?
8. Which country or place is next on your list?
9. What is the bravest thing you want to do this year?
10. What would you like more of in your life?

How to Ask Deep Questions Without Sounding Like an Interview

Even the best question can feel like a job interview if you fire three of them in a row. Mix them in, share your own answer first, and let the conversation wander.

• Warm up first. Start with something light. If you are not sure how, our guide to starting a conversation online covers the first thirty seconds.
• Answer your own question. It shows the level of detail you expect, and it makes it safe to be honest.
• Follow, do not script. The next question should come from their last answer.
• Let them pass. "Ask me later" is a perfectly fine answer.

Where These Work Best

Deep questions are at their best in a private 1-on-1 video chat, where you can see a face change as it thinks. Just keep in mind that depth does not require detail: you can talk about values, memories and plans without ever sharing your address or workplace, which is the idea behind anonymous video chat.