Talking to a stranger sounds super scary for many people. But it’s a necessary thing to do in many cases. Some of the most insightful conversations that I’ve had were with strangers, e.g., a marine lawyer sitting next to me on a bus, a factory worker waiting in an airport queue right behind me, a speaker seller sitting next to me on a flight. By definition, a stranger lives a different life and has different perspectives. Therefore, there’s so much we can learn from them.

Remember

• A stranger has more in common with you than you think. Even if you are meeting a celebrity or very succesful person, remember that he/she is a human first of all. He/she probably has interests, preferences, and quirks, just like you do
• Be yourself and be open to share your own stories. If you don’t open up, the other person likely won’t either
• There will be awkward and even uncomfortable moments. That’s totally fine
• You can memorize some questions to have in your pocket and use them flexibly as you see fit

Strategy

• Find a common ground to build a connection
• Find out about what the other person cares about or are passionate about. Then ask them to talk more about it
• Ask open-ended questions: What? Why? When? How?
• Ask about things that you are genuinely interested in. If I have a decision or topic that I am learning about, I usually bring up to ask about thoughts and opinions of whomever I am talking to, either a friend or a stranger
• Take some risks to explore new grounds with out-of-the-blue questions (examples below)

Sample questions

• Opening questions: open-ended and easy to answer
  • Have you visited Boston before?
    • [If yes] Are there places (e.g., restaurants, museums, shops, café, etc.) that you’d recommend?
    • [If no] Are there places that look interesting?
  • What did you do this summer?
  • What are you up to in the next two months?
• Space
  • Do you already know someone in Boston?
  • What do you look forward to the most in living in Boston?
  • What are you most concerned with?
• Hobbies
  • What do you enjoy doing in the weekend?
  • When you have free time, what do you enjoy researching or learning more about?
  • What’s your favorite guilty pleasure?
  • Any favorite fall activities now that fall is coming up?
  • What are your favorite movies or TV shows? Music? Books? Podcasts?
• Work/Career
  • What do you do?
  • How does X work?
  • What do most people misunderstand about your field?
  • If the other person is starting an MBA soon, you can ask:
    • I’m not familiar with an MBA. Can you tell me more? What are some paths that people usually take out of an MBA? What paths are you considering?
    • When did you know that you wanted to do an MBA?
    • Why do you want to do an MBA?
    • How does an MBA program work (e.g., types of courses, etc.)?
• Personality
  • How would your best friend describe you?
  • What do most strangers get wrong about you (e.g., personality, thought process, strengths, weaknesses, etc.)?
  • What are you most confident about?
  • What do you secretly want to brag about but you don’t to most people?
  • What are you not so confident about?
  • What excites you these days?
  • How can careful planning and rational thinking save your brain from being exhausted?
  • How much spontaneity vs planning do you prefer in planning a trip or your every day life?
• Family
  • What do your parents say about your current plan?
  • Do you have any siblings?
  • Who influenced our thinking or personality the most?
  • What do you usually debate or disagree with your parents?
• Explore new grounds: When you feel a bit more comfortable with the person, you can choose to ask any of these random questions to explore new topics.
  • What do you have an abundance of?
  • What do you want more of?
  • What do few people know about you?
  • What have been on your mind in the past month?
  • What have kept you up at night recently?
  • In the past few years, what new beliefs, behaviors, or habits have most improved your life?
  • Putting money, career, and family aside, which city or country would you love to move to for a year?

Hopefully these tips and sample questions allow you to more easily enjoy conversations with strangers. If you are an introverted person, it feels intimidating at first. But once you step out of your comfort zone a few times, you’ll realize that it’s not that uncomfortable.