5 Tips on Starting Conversations on Public Transit from the Young Urban Unprofessional

Over the past month I’ve met a wide range of people on the train and each person has a different story, it was truly an adventure.  I met a nanny for the children of two rich lawyers, a yoga instructor who also has a PhD in Computer Science, a tennis pro who offered me a free tennis lesson, a 90 year old man who worked at my job 30 years ago, people going to Boston for a booty-call, various compulsive travellers, and then people who moved to this country for a “better life” (Haiti, Peurto Rico, Sweden, and others).  All of these people had two things in common, 1.)  They all ride the train together and 2.) Despite their seemingly closed-off attitude, they were all willing to chat if I started the conversation.  Here are five tips that I learned throughout this month of starting conversations with strangers on public transit.  I’ve tried them elsewhere (i.e. bars, networking events, work, etc) and they work.

1.)  Have Something in Common – Starting conversations are awkward almost every time, especially when the other person seems uninterested in conversation.  However, if there’s something that you both have in common then things become much easier.  For me this month it was things like, bikes falling over on the train or just being in the way, the conductors being incompetent or extra friendly, a drunk or homeless guy making a ruckus, late/stalled trains/buses, and literally anything else that you both have to experience.

2.)  Tell a Story about Yourself First – After the initial conversation has started, share a personal story about the common thing you both just experienced.  For example, a bike falls over and you make a comment, share a story about a time you saw it happen somewhere else or that it once happened to your own bike.  This helps keep the momentum going.  I found that many people are unwilling to open up to you if you just keep asking them questions.  It gets pretty annoying to be bombarded with rapid questions right from the beginning, plus you’ll kind of look like a creepster.  So if you open up about yourself and your own experiences first, they will be much more willing to spill their guts as they most frequently did with me.

3.)  Talk about Work/School – These are always safe subjects to talk about with most strangers.  You don’t want to get too personal too fast, but people spend a majority of their life in school or at work so they’re generally willing to share their story.  Ask lots of questions and share little tidbits about your own school/work experience.  However, if you keep the emphasis on them and keep asking lots of good questions, they’ll elaborate just because someone is willing to listen.  There’s not much that’s more flattering than someone who’s interested in your career/degree.  Many of my conversations this month have revolved solely around the other person’s work even though I knew nothing about what they did professionally.  More often than not, their stories were fascinating.

4.)  Talk about the Local Sports Team – At least here in Boston this worked for me EVERY SINGLE TIME.  Granted people here, unlike other areas of the country, are OBSESSED with the Red Sox, Patriots, Bruins, and Celtics.  Perhaps I’m not a great Bostonian because I’m not a hardcore follower of any particular sports team (I prefer college sports anyway).  I’ve played competitive sports my entire life, I’d just rather play them than watch other people play them.  With that being said, I only know the highlights of games in the area.  This has been enough to start and keep conversations going even though I might not even know who won last night.  Guaranteed if you get on the train, you could pick out a random person, start talking about the Red Sox and you could have a conversation until the end of time, it’s an easy “in” toward a more meaningful conversation.

5.)  You Have Two Ears and One Mouth, Use Them Proportionally – This goes for any type of conversation; you should listen twice as much as you talk.  I generally have a tough time with this because I’m an extrovert who likes to hear myself talk.  So this month was definitely a challenge to sit back, ask questions, and place the emphasis on someone other than myself.  It was a great exercise in listening and as a result I was able to sustain many conversations.  I broke this rule a few times, simply going off about some idea or another  When I would get home to write a blog post I would realize that it was just me ranting with a stranger, not really an engaging post and not really the point of this month’s challenge.

Before this month, I found myself, like many others on public transit, slipping into autopilot mode; iPod, book, newspaper, sleeping, etc.  Does that sound familiar?  Mildly more fulfilling than driving, but still lacking that element of social connectedness that we all crave as humans.  As I said at the beginning of this month, I spend between 500-600 hours on public transit simply commuting to and from work, not counting just getting around the city after work and on the weekends.  I really just wanted more out of that 500 hours of my life.  Instead of lecturing on the pros/cons of public transit vs driving, I wanted to simply expand and improve my experience by getting to know the people I commute with every day.  I also wanted to test the hypothesis that even in a city, people are generally very friendly and willing to chat even though they might have a closed-off attitude.  I encourage everyone pick a stranger on the train/bus/air plane and try the tips above.  Leave comments below if you have additional tips, I’m always looking to improve.  Be sure to check out my October Challenge; Photographing My Non-Work Life Randomly Every Hour.

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