Category Archives: September – One Conversation per Day on Public Transit

September’s challenge is to start one conversation with a stranger every day on public transit in Boston. I commute on the train as my primary mode of transportation and last year I spent somewhere between 500-800 hours using public transit. Now it’s time to get rid of the iPod, the book, and the auto-pilot attitude in order meet some of those people I see every day. I’m hoping that this 30-day experiment will improve that 500-800 hours/year of my life I spend commuting around the city. I’ll blog about my experience and tell the stories of people I encounter.

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 … Continue reading

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Mr. Bartender and the Peppermint OJ Pick-Me-Up

Mr. Bartender has two jobs, one of which is with the company I work for and the other one is as a Bartender just outside of Boston.  He’s got a pretty thick southern accent (hard to understand at times), a … Continue reading

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Miss High Speed Adventure Racer

This was the first time I’ve seen Miss High Speed Adventure Racer on the train.  I recognize pretty much everyone who waits for the train every day so it’s always pretty obviously which people aren’t the usual commuters.  I locked … Continue reading

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Mr. Small World’s 90th Birthday

Today I sat down on the commuter rail across from someone who seemed like they’d be talkative but was really just into reading their book.  So I decided to respect their privacy and move on.  At the next train stop I … Continue reading

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Miss “Real” Mom

On the way home from work I got to the train station early and started talking to this guy sitting next to me on the bench.  I thought it was going to turn into a great story for my blog … Continue reading

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Mrs. Major from Harvard

Today I started to see results from my month-long quest to meet new people on the train.  People I’ve met have sought me out and I’ve been able to interact with more than one of them at a time.  This … Continue reading

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Misters and Misses-es of the Military

Today I sat down alone on one of the fold-out seats on the commuter rail and I leaned my road bike up next the the other seats, i.e. blocking four usable seats per the usual.  As the train was about … Continue reading

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