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.

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 docile demeanor, and an incredible work ethic.  I wasn’t really able to get out of him what exactly he does at my company but we did talk about how tired he was.  He works 10-20 hrs/day depending on the week and he gets Sundays and Mondays completely off.  He takes the MBTA trains into Boston every morning and then commutes on the commuter rail out of the city to go to work.  After spending 8 hours at work he goes to his bartender job where he commutes into the city and back out again.

He’s been doing the bartender job for more than 20 years at that particular bar and he’s just not willing to give it up.  He’s best friends with his usual customers and he enjoys the social aspect of it; meeting new people and hearing their life stories.  However, when he found that he needed more money to pay some bills, he picked up this second gig at my company through an old friend of his.  He looked exhausted and I made a comment about how he must have to drink a ton of coffee.  He said that he’s not much of a coffee drinker.  Surprised at how he works so hard without a pick-me-up I asked him how he does it.

He said he had a secret drink.  He mixes 50:50 orange juice and apple juice (or pineapple juice depending on what he’s got around) but then puts in 3 peppermint candies in the bottom of it.  He said it works like a charm.  Back in the day he use to use it as a meal replacement while traveling in foreign countries when he was scared to eat the food.  Many times he would be travelling through a sketchy area of some 3rd world country and when he didn’t trust the food he would find a place to get the OJ/Apple/Peppermint drink combo.  He seems to have a fixation with the peppermint candies because he pulled 10 of them out of the front pocket of his jeans to show me.  I’m sure he had a bunch on hand while travelling so all he needed was a place that sold OJ and Apple Juice, generally a safe choice in the 3rd world.

Today he was heading to the bar after work for an Oktoberfest celebration.  He expected things to get crazy, “As dey usually do bout’ dis time of yeayh.”  I asked him what was the craziest thing he’s ever seen at the bar.  He just kind of laughed and said he’s seen literally everything.  He almost seemed too tired to think about the antics of the past 20 years.  At this point we got off the bus and went our separate ways.

I see him every day on the train so I’m hoping that he’ll be another person I can at least waive to or maybe I’ll get him to tell me some crazy stories from his life as a bartender.  I’m also interested in his travels because it seems like he’s been to some interesting places.  I’m looking forward to trying his drink to see if it’s really as magic as he says it is.  You can’t loose with fruit juice as a pick-me-up but I’m interested in how the peppermint will help out.  He seems like a nice guy so I’m sure we’ll have a chance to chat again.

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 up my bike at the station and started to walk down the stairs to the platform.  Sort of under her breath she said something like, “Yeah last time I rode my bike here I almost died”.  I replied, “Sounds like almost every time I ride my bike in Boston”.  So instantly we had something in common so we chit-chatted while we waited for the train.  No deep life stories this time, just a 22 year old girl at warp speed talking about working, family, running, and exercising.  It went something like this:

She studied science and finance in school, graduated this past May, and is now doing marketing for a science-based company in the area.  Her company does her dry cleaning and she has a free personal trainer at the gym in the basement of her work building (how awesome is that!).  She bikes to work a few days a week, approximately 20 miles each way so she’s definitely pretty intense.  Her intensity for exercising was definitely correlated to her intensity for trying to cover as many topics in one conversation as possible (in a good way, but also in a take a deep breath and sit down to prepare yourself kind of way).

She’s training for a half marathon in Boston with the hopes of eventually running the Boston Marathon.  I ran the marathon in 2010 so we talked about training for a while.  I ran it through the Tufts Marathon Team which is a largely non-competitive fundraiser with 200 other students/faculty/family memberes.  Like me she knew that she would have to join some fundraising team in order to run the marathon as the qualification times are pretty serious for people in our age group (Men = 3hrs 10min aka 7:15 pace, Women = 3hrs 40min aka 8:24).

At the finish with former Tufts President Larry Bacow, huge stud and marathoner himself even though he left us to go teach at Harvard :(

We then went immediately to adventure-style races like Tough Mudder, Spartan Race, Ragnar, and Reach the Beach.  She had never done any of them but she has read about them extensively, in almost an obsessive compulsive kind of way.  I’ve done Ragnar three years in a row and definitely plan to make the Spartan Beast Race a yearly event.  Ragnar is very similar to Reach the Beach in that they are both 200 mile (ish) relay races where you have a 12 person team split into 2 vans and you run a relay over 24 (ish) hours. They have races all over the country but we’ve always done the one in the Northeast from New Haven to Boston.  Here’s a pretty sweet 10 minute video done by ESPN on Ragnar in case you’re interested and/or bored at work/school.  The video features the original Ragnar through Utah, looks AWESOME.

So we talked about this quite a bit and then shifted to the obstacle course type races and the differences between them.  I recently did the Spartan Beast race in Vermont up and down Killington Mountain.  It was absolutely the most SAVAGE race I’ve ever done, there’s no other way to describe it.  You can be good at running, you can be good at other sports, i.e. there’s talent involved, not with this race because it’s pure grit.  It’s 13 miles running up and down Killington with 20 (ish) obstacles.  Definitely tougher than the Tough Mudder because with the Spartan races they actually crush you when you fail to complete an obstacle, the penalty is 30 burpees, Tough Mudder you can just walk around the obstacle with no penalty.

Anyway, we talked about all of these cool races and I could see her eyes light up.  Not with mere interest or excitement, but rather with some sick, twisted sort of self-punishment you can only find in people who enjoy these types of events.  Our conversation covered school, family, where we were raised, jobs, athletics, different exercises, different races, a little bit of politics, and some about riding public transit.  Definitely a whirlwind conversation but I’m glad that me and Miss High Speed Adventure Racer got to “bro-out” about different races and whatnot.  She just started working out on the same train line as me so I’m sure we’ll have the opportunity to talk 1000mph again, I’m sure it’ll be sooner rather than later.

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 scoped out my next (victim) new friend.  It happened to be an old man who was reading a Boston Metro with the headline of, “Boston Tear Party” due to the Red Sox closing out the season in a blaze of NOT glory.  He was a tough shell to crack, largely because he was an old man who was hard of hearing and it was also early in the a.m., not a time that people are particuarly approachable.  I practically had to yell to him so I’m sure the other a.m. commuters were not amused.

I don't follow the Sox as well as a Boston yuppie should but you can't avoid hearing about them getting obliterated this September. It really takes a toll on the whole city.

I asked him if he watched the game, usually a quick win with strangers in Boston, but he said no.  After a few moments of me pretending to read my book I asked him if he was from around here.  He told me he lived in the same town that I work in.  Not sure what he was doing travelling home at 7am in the morning but oh well, I’m sure he had a good reason so I didn’t bother to ask.  I told him where I worked and it turns out that he worked at the same company 35 years ago as a pulp and paper engineer (he retired then too, crazy to think that he’s been retired for 10 years longer than I’ve been alive).  Then due to us having worked for the same company (i.e. common ground) the conversation became easy and natural.  Thus he launched into his life story…

He started by going to school at Syracuse University for free because he decided to study pulp and paper engineering.  Then years later, his/our employer sent him to the University of Maine to get a masters degree in pulp and paper engineering, also for free.  I was familiar with the program because it’s heavily endorsed by the state despite the fact that it’s a dying industry with mills closing all over the state, leaving behind nothing but ghost towns and poor people.  It was there that he started looking for property.  He had found a good lot in Unity, ME with 100 acres of land for next to nothing.  However, he didn’t put his money down in time and some family from California bought it without ever even visiting the place.  Then he looked around the coast figuring that ocean-front would be a good alternative to having 100 acres (in the middle of nowhere Unity).  So he finally rested in a great little coastal town where he still owns a house.

That's one huge ream of paper. Too bad pretty much all the mills in Maine have closed, they unfortunately left behind many ghost towns.

He then met his wife, a 35 year old widow with two kids who lost her husband when he was 33.  She had gotten a job at the University of Maine as a researcher after his death to try and pay the bills.  He had met her there while he was in his masters program but it wasn’t until he came back a few years later that things really took off.  They ended up marrying and having three more kids, five in total.  He said his wife was the best wife he could ever imagine and that she passed away a few years ago.  It seemed very much that he was simply biding his time until he would too pass away. 

At this point he mentioned that his 90th birthday was on Saturday, October 1st (aka, born 10-1-1921!!!).  He said he had family far and wide who were coming to celebrate with him on Saturday.  For whatever reason his extended family has settled in each of the four corners of the U.S.; northeast, southeast, southwest, and northwest.  He told me that his biggest concern about his old age and eventual death was that his kids would misuse and fight over his oceanfront property in Maine.  It was a nice property and worth some pretty good money these days.  He could see them fighting over who got to use it on the weekends/vacations or whether or not to sell it and make a boat-load of money.  He said that he didn’t worry about his kids because they were pretty congenial but he was worried the most about his grandkids and how they would behave with each other.

A quintessential Maine lighthouse on a rocky shore, Maine's not much for beaches. Fun fact: If you stretched out Maine's coastline, it would reach the entire length of the east coast.

I was able to keep the Maine conversation going for quite a while because I was able to add in comments due to my being raised there.  I have family all over the state and his family had come to rest there.  Despite the fact that everyone in Maine is somehow related or best friends with somebody’s brother, neither of us recognized the other’s family name, oh well we tried.  The world is small just the same. What are the chances that I’d meet an engineer who worked for my employer (albiet 35 years ago) and also lived in Maine for much of his life, all on the commuter rail train at 7am.  The train got to our stop, we shook hands, I wished him a happy birthday, he said it was nice talking, and we went our separate ways.  A very happy 90th birthday goes out to Mr Small World, nice hustle.