Toby: I’ve moved cities several times, and often found myself in situations where my social circle was limited or at parties where I only knew one or two people. Like many people, I sometimes found it difficult to be around a lot of strangers, however I always really enjoyed getting to know people and found that many of my best memories seemed to involve meeting new people and having some sort of unexpected interaction.

After a particularly interesting night out with my friend Jeff Beene at an Iron Chef Louie event, which involved a Chicago metalhead, a designer visiting from Germany and a 3am bike ride to Chinatown, we started discussing evenings past that really stood out in our minds. While we had many great times arguing about politics or going out with a group of friends, he also felt that these unexpected interactions were the most memorable.

Such outcomes could never really be planned for, but we decided to see if we could make them happen more often. We decided to try talking to people we didn’t know every time we were out¹. Of course, it wasn’t our intention to annoy people, so we also decided we would immediately leave people alone if they seemed irritated.

We stuck to this over the course of several months. There were several lessons that I took from the experience:

• Almost everyone is surprisingly receptive to a conversation from a stranger — if they aren’t they’re almost never rude about it
• Large groups of people are the most receptive, smaller groups are more likey to be having intimate conversations that they don’t want interrupted
• Since almost no one is out on Monday night, it’s best to find a “Service Industry Night” — these nights are really fun and full of very social people
• It’s good to find a balance between telling funny stories and asking questions
• Almost everyone is really excited about something
• It’s extremely challenging and really fun to avoid asking or being asked “what do you do?” for as long as possible²

As expected, the process led to several interesting outcomes:

• A journalist wrote about us in a local newspaper as part of a review of a bar
• I was given 3 unsolicited phone numbers
• We started getting complimentary food and drinks at several places
• We got in more fun arguments, only they were with people we didn’t know, which gave us new perspectives — I now believe that talking to people outside ones normal circle is very important for the development of new ideas
• We ended up at places in the city we would not have thought to go otherwise
• I met Dana Zemack, someone I would probably never have met otherwise, who eventually became one of my best friends

Most importantly, socializing at all times and making an effort to meet people became something of a habit, long after we decided to stop making it a rule. As a result, I actually have more fun when surrounded by new people and have a general feeling of connectedness, almost as if people who were once anonymous no longer seem that way.

Brooke & Toby: Later we had fun and surreal experience talking to strangers in clubs in Miami, which will be the subject of a later post…

1. I did live in the South and California for a while, so I know this doesn’t really seem like unusual behavior to some of you, but in much of the Northeast it’s much more unusual for strangers to talk to each other [↩]
2. this is particular to the USA, in other places it’s much easier [↩]

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