How to have better conversations at bars

I’m on a Tim Ferriss kick, and one of the things I notice about Tim Ferriss is that he asks great questions. They make you think about things you wouldn’t typically think of. They challenge you and excite you. He does this for business and lifehacking purposes, but I found another application for great questions: meeting new people. I did this tonight and it worked out wonderfully.

After the welcome party for We Roam at The Clubhouse in Buenos Aires, we went to another bar down the street. Here I met an Argentinean girl who spoke really good English. After 20 seconds of small talk I admitted I don’t like small talk in social drinking and partying environments. It just doesn’t excite me. I asked if she minded if I asked her a series of questions instead. She was intrigued.

The first question I asked her was one I learned from an amazing AirBNB host in Savannah, Georgia. She loved to party and have a great time and had sons as old as me. Anyways, she asked me who was in my immediate family. I told her my mom, dad, and sister. Then she asked me: Who would you rather do a cross country trip with, be stranded on an island with, or live with? And why?

The question in writing is unexciting, but when I was asked this I was intrigued. It’s because it wasn’t small talk. It was a way for me to open up to someone I had only known for an hour in a fun way. Last night I was on a roll with this question but couldn’t come up with any more on my toes to ask my new friend. Looking back I should have asked about something related to science fiction and time travel.

To make sure I don’t get stuck again, I’m going to create a list of “big talk” questions to ask to new people I meet. Thanks Ferriss, and thanks AirBNB mom.