Whether deep and detailed or lighthearted and limited, conversations are how we create connections with other people. These bonds not only warm our hearts, they can also expand our perspectives in compelling ways. Sometimes though, the idea of trying to start and maintain a conversation can feel intimidating. Keep in mind, comfortably connecting to other people through discussion is a skill that can be learned and improved.
- Practice noticing both the verbal, and nonverbal, ways that people communicate. When you’re somewhere that you can comfortably be in “observer” mode (coffee shop, airport, etc.), unobtrusively take note of how people interact with each other. How do they signal interest in having a conversation? How do they indicate that they’re done? What do you notice about how much (or how little) eye contact people are comfortable with? What about other body language? Tone of voice? How do these communication details show up in your conversations?
- If you know you’re going to be talking with someone you’ve previously met, remember what you learned through those conversations. What are their interests, challenges, etc.? Develop a couple of questions around those. If you’re talking with someone you haven’t met before, start with something pleasant and low-stakes. Maybe offer a compliment plus a question: “Your jacket looks perfect for this weather. Where did you get it?” or “This is such a great coffee shop. Do you have a favorite item?” A shared observation is also a good place to begin: “The turnout for this event is wonderful! Have you come before?” or “The weather is glorious! What do you enjoy doing on a day like today?”
- “Yes or no” questions can block conversation, while open-ended questions help keep it flowing. Starting a question like a journalist—who, what, when, where, or how—invites your conversational partner to fill the blanks.
- It’s been said that for good conversations, it’s more important to be interested than interesting. This means slowing down and really listening, not so that you can prepare a sparkling response, but because you’re offering the gift of your attention. Author Maya Angelou believed that in every interaction, we all are looking for answers to four unspoken questions:
- Do you even notice I’m here?
- If you do notice that I’m here, do you care…or not?
- Am I enough as I am, or will I have to change in order for you to care about me?
- Can I tell that I’m special to you, just by the way you look at me?
Real listening is part of how we answer these questions with care and consideration.
- What about when you want or need to end a conversation? One way is to signal the upcoming transition. This can sound like, “I’ve got to leave in a second, but could you tell me a little about___?” or “I need to go, but before I do, could you quickly update me on___?” This allows you and your conversational partner a chance to close out the conversation together instead of abruptly cutting it off. A simple, “Nice chatting with you. Take care!” is also a straightforward and respectful way to wrap things up. If someone indicates that they’re leaving the conversation, honor their need to move on. Don’t keep talking or asking questions.
- It’s possible that when you try to start chatting with someone, the other person may not be interested. This doesn’t mean that you’re not worth talking to or that you should avoid initiating conversations. It means that this specific person at this specific time wanted something else. Congratulate yourself on recognizing and respecting their cues and know that your social awareness will serve you well in future conversations.
But once you’re visiting, how can you get past “What do you do?” Novel questions can help develop the dialogue:
- Who’s your biggest role model?
- What’s your favorite thing that you’ve read or watched lately?
- What’s some solid advice you’ve learned? How did you apply it?
- What are your go-to comfort foods?
- Where’s your dream travel destination?
- When do you feel most “yourself?”
- Do you have a favorite quote or motto that you live by?
- If you could instantly become an expert in something, what would it be? Why?
- If you could have dinner with anyone, alive or dead, who would you pick? What would you want to discuss?
So, take a chance and break the ice. There could be warm conversations on the other side.

