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How to Start Conversations with Strangers

Connecting with StrangersHow do you enter conversations with people you don’t know?

I grew up with gregarious parents and have enthusiastically emulated them. Although my mother referred to herself as shy, I never observed her that way. She seemed to be able to engage with people in various scenarios. My father was raised in South Philly (home of the iconic pugilist character Rocky) where talking to people on the stoop or street corner was commonplace. He learned how to communicate with those from all walks of life from his own blue collar, working class sensibilities. No matter where our family went, it seems my father always knew someone, and it took forever to say goodbye as we attempted to take our leave. I would also marvel as he would strike up conversations with people he had never met. 

As a therapist, I work with clients who, in some cases, experience social anxiety, which is defined by the Social Anxiety Institute as “the fear of interaction with other people that brings on self-consciousness, feelings of being negatively judged and evaluated, and, as a result, leads to avoidance,” and don’t have the comfort level that would allow them to do that. The jury is still out about whether it is nature or nurture.

What some tell me is that they don’t know how to initiate or join in. I think of it like jump rope and knowing when and how to jump in without tripping over the rope held on either end as it spins over your head and on to the ground.

Call out your inner nerd

I have also used a tool with my teen clients who often walk down the hallways at school, head down, as they avoid eye contact, wishing themselves invisible. I ask them to imagine cartoon character-like thought bubbles above the heads of their classmates as they make their own way to classes. In each one is a self- deprecating message, like “OMG, I can’t believe I’m such a dork.” “How could I have blown that test?” “She’s never going to go out with me, since she’s out of my league.” “Why did I wear this dress today? I look so fat.” By the time we get through this exercise, they are usually laughing as they realize that everyone harbors an inner nerd who thinks others are way cooler than they are.

I add to it that when I was their age (more than four decades ago), I never felt like one of the cool kids. It wasn’t until I attended my 35th high school reunion that some of those I looked up to and wanted to be like, informed me that they thought I was one of the cool kids and wanted to be like me, including one who said he had a crush on me. I asked, “Couldn’t you have told me that back then? It would have prevented a lot of adolescent angst.”

What keeps people from throwing caution to the wind and jumping in?

  • Fear of not having anything meaningful to say.
  • Stumbling over their words or stuttering. I tell my clients the story of actor James Earl Jones whose stuttering was almost debilitating until a teacher helped him to recover by having him read poetry aloud. Jones was featured on the website for The Stuttering Foundation.
  • Fear of forgetting what they want to communicate.
  • Poor self-image and a belief that they are not worthy of another’s time or attention.
  • Reinforcement by caregivers and other adults of their worst perception of themselves.
  • Not wanting to be rude by joining a conversation without invitation.
  • Feeling under-educated about current events.
  • Somatic symptoms such as dry mouth, heart palpitations, perspiration, facial flushing, and dizziness.

Recently, when I walked into a local gathering place to hear a friend perform, I asked to sit at the end of a table where a few others had already made themselves comfortable, beverages in front of them. A woman smiled and motioned me to be there. I enjoyed the music and then overheard part of their conversation about having been married by a monk in Thailand and (with only a slight hesitation), I invited myself in and inquired about the experience. As an interfaith minister, I am fascinated about how couples meet as well as their unique wedding ceremonies. They welcomed me in and a conversation ensued about the state of the world, relationships, The Dalai Lama — who I interviewed in 2008 — spirituality, life in our town, and serendipity/synchronicity. None of that would have happened, had I not been willing to ask to sit with them or initiate conversation. I am also an adept listener who is truly interested in hearing other people’s stories.

I had inquired of others on social media: “What allows you to converse with strangers?”

“I am good at interviewing people, so I like to ask them questions but not private stuff. Many people like to talk about themselves and like knowing someone is interested. I am not good at walking up to people and introducing myself. I do like to listen though.”

“I am very good at walking up to people and introducing myself, but insecurities immediately set in — about people being silently turned off by what I’m saying, about talking too long, about dragging out unwelcome topics — which sends me into a communication death spiral of anxiety & self-consciousness.”

“I can go into a ladies’ room and come out with three new friends.”

“I’ll talk to anyone. My husband says he’s learning to do the same thing. It can be the weather, kids, or anything. Went to the post office for my house and a woman came in. We ended up taking about kids, grandkids, her thyroid issues, my thyroid issues, her recent bone scan.”

When I moved from CT to PA, I knew almost no one and had no ready-made social circle. I am naturally introverted and have some social anxiety, so I would bring yarn with me most places. I crochet and often people would stop to talk to me, comment on what I am making, and then sometimes start a longer conversation. I still bring yarn with me a lot of the time. Most of what I make are gifts for people, usually new babies. If no one talks to me, I am still enjoying something I love and making something beautiful for someone.”

Remember that everyone you now know, and love was once a stranger and your relationship with began with a conversation.

How to Start Conversations with Strangers

Edie Weinstein, MSW, LSW

Edie Weinstein, MSW, LSW is a journalist and interviewer, licensed social worker, interfaith minister, radio host and best-selling author.

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APA Reference
Weinstein, E. (2018). How to Start Conversations with Strangers. Psych Central. Retrieved on October 30, 2020, from
Scientifically Reviewed
Last updated: 8 Jul 2018 (Originally: 17 Jan 2018)
Last reviewed: By a member of our scientific advisory board on 8 Jul 2018
Published on Psych All rights reserved.