Talking to strangers

The Internet has tons of resources to help you develop your conversation skills, not to mention your confidence (it’s so nice to learn that you’re not the only one who is apprehensive about talking to strangers). I’ve also listed some articles/projects where people document their attempts to talk to strangers, some funny articles that tap into the real trickiness that can accompany interactions, some videos, and even some articles that argue against talking to strangers. Finally, I’ve listed some organizations that encourage people to talk to one another, and various reports that do the same. If you have suggestions for further resources I should list (or any links are broken), please email me. If you find these helpful, let me know – I’d love to hear from you. Good luck in your adventures!

NOTE: Press coverage of my research, blog posts that I have written and podcast interviews with me can be found in the Research area of the website

Tips on how to talk to strangers

  • Article with TONS of useful links, with tips from what to talk about to, importantly, how to end conversations.
  • The Art of Manliness (which, as a woman, I prefer to think of as the Art of Living Well) has tons of great resources about how to talk to strangers.  Start with this ultimate guide on “How to Make Small Talk”, full of great advice, and then check out the resource lists for these two podcasts (1 and 2).
  • Conversations with strangers almost necessarily start with small talk, but you can learn ways to enjoy these conversations more, and to turn them into something deeper. Time management guru Laura Vanderkam shares tips learned from small-talk expert Debra Fine, who is also mentioned in this New York Times article with “3 tips to have better conversations” and this podcast
  • Laura Vanderkam’s “7 ways to gracefully exit a conversation”, including having a wingman.
  • The author talks about she’s always been shy, why she decided to “get it under control”, and how she did it (though it’s still hard). link
  • The same author talks about how to survive a party (or other event) where you don’t know anybody. She talks about how to find someone to talk to, and what to say once you do.
  • An introverted business school professor shares “how I’ve managed to strike the balance between meeting new people – and being exposed to interesting new ideas – and not having to initiate awkward conversations”. link
  • Another introverted author talks about how to connect to people at a conference (“a massive space with lots of people, noise, and activity”). I love her tip on helping yourself by making others feel comfortable – that’s a trick I use myself.
  • The insightful Jeff Haden’s “10 habits of genuinely charming people” could be co-opted to help grease the wheels during your conversations with strangers.
  • Similarly, you might want to adopt some of these “10 rules of a great conversationalist”, including being genuinely interested in your conversation partner.
  • TED article with 3 tips on how to prolong and have more interesting conversations (tip 1 is “Ask for stories, not answers”).

People reporting on their attempts to talk to more strangers

  • The not-so-successful experiences of a reporter who challenged herself to talk to fellow commuters every day, as part of Loneliness Awareness Week.
  • Results of a 21-day experiment to talk to more strangers. I love how the author discusses how difficult it was at times – I’ve felt all those things. At the end he offers 4 tips for starting conversations. Bottom line: “Almost every interaction left me feeling a little happier. I also felt like I learned new things by talking to people from different walks of life who I wouldn’t normally meet.”
  • Results of a week-long experiment to talk to people on the train. Again, I can relate to the authors difficulties in getting started and maintaining a conversation, and to the fun in the successful ones. Her conclusion: “When there was an actual jumping-off point for a conversation — a book, coffee-flavored chips, super-cool pants — the other person was very receptive, and it resulted in an actual back-and-forth. As nervous as I was to break the ice, those experiences were surprisingly fun.”
  • After a long flight, during which she observed two men bond (to the extent that one invited the other to his birthday party), an introvert wondered what she was missing out on by forgoing conversations with strangers. Read about the hilarious Jessica Pan‘s journey to overcome a fear of talking to strangers. Also, check out her brave, honest, funny book “Sorry I’m late – I didn’t want to come”, describing her adventures in extraverting.
  • Projects telling the stories of average people, encounters with strangers




  • Funny article (with cartoon drawings!) about some of the awkward situations that arise when interacting with friends and family (e.g., “The Handshake/Hug Decision of Doom” – “There are different rules for everyone and nothing’s clear—Do I shake my grandfather’s hand or go for the hug?”), acquaintances, and strangers (e.g., “Nice to Meet You / Nice to See You Disaster” when “you’re not entirely sure of whether the person you’re introducing yourself to is actually a stranger”).
  • Funny, because oh so true. “Everything I am afraid might happen if I ask new acquaintances to get coffee”.
  • Fake news in the Onion, “a new report…revealed Wednesday that it’s never okay to just start talking to someone you don’t know”. Ironically, it lists many effective ways to connect with strangers (e.g., sharing a common situation or an interest).

Articles arguing against talking to strangers

  • “Surely the point of living in a city is that you don’t have to talk to anybody. That’s certainly a big part of why I moved to one.” link
  • Number 1 on this list of 11 ways to embarrass yourself in London is “Speaking to anyone you don’t know on public transport”. According to this article, “most people will think you’re either crazy, chatting them up, or are about to rob you.”

Organizations encouraging people to talk to one another

Reports and white papers that encourage talking to strangers