Alice Lee | 30 days of coffee and conversation

When you ask a random person out to a platonic coffee chat, you begin as strangers.

Thirty minutes of conversation pass, sprinkled in with caffeine and laughter. You listen to his or her story — background, what he or she enjoys doing and maybe even a little bit about how his or her day went. Then you share a little about yourself. There is no fluff, because these few calm moments in our busy lives don’t contain an ulterior motive. You’re just there to get to know the other person in the most “you seem interesting so let’s be friends” way possible.

By the end of it, you’re no longer strangers. You’ve become acquaintances, maybe even friends.

Some people might find the idea of grabbing coffee with a stranger a rather weird and awkward activity. If someone I didn’t know had approached me a year ago, I would have been weirded out. But then I got involved in the world of start-ups and tech, where — contrary to what outsiders might think — it’s acceptable to ask a stranger out to a friendly coffee if you’d like to get to know them.

It’s a mutually beneficial interaction. Through coffee dates, I’ve found mentors, fellow photographers and some great friends.

Last month, I set myself a challenge to get coffee with a new person every day for 30 days. The coffee, to be honest, was the vehicle. My real goal was to forge connections with people I’d normally never interact with.

By the end of this week, I will have completed my 30-day challenge. Every interaction, every new acquaintance and friend that I’ve found so far has made those 30 cups of coffee completely, undeniably worth it.

Most vividly, I remember my chat with Wharton and College junior Katherine Long — who I’d always wanted to get to know after taking the same Legal Studies class. Our original 30-minute coffee stretched into three hours of lively conversation, dinner and the unexpected discovery that we share a ton of mutual interests.

On Tuesday, I sat across from Engineering sophomore Isaac Sukin at Capogiro and talked about our shared experiences in freelancing. We ranted about pricing (or really, I did) and talked about tech for an hour.

Before spring break, I started talking to a guy while standing in line at Hemo’s. He was wearing a T-shirt with the Twitter logo and I was wearing a foursquare tee. That’s how the conversation started.

A week later, I met with 2004 College graduate Alex McCauley in the gorgeous Twitter headquarters in San Francisco. Next time I’m back in town, we’re getting burritos.

I would have missed out on getting to know Katie, Isaac, Alex and the dozens of wonderful people I sat down with had I relied on the traditional ways of meeting people.

Just take a moment to think about the last 10 people you met: maybe you were introduced by a mutual friend. Maybe you share a hobby, class or belong to the same sorority. Maybe you met because you were at the right place at the right time — you just happened to be placed in the same hall freshman year or you drunkenly crossed paths at a bar last week.

But these seemingly random connections are largely forged through pre-determined structures in our social environment — which is actually quite limiting.

Most coffee dates I’ve have last around an hour. And in that hour, most people have had something interesting to say whether he or she was a stranger or a friend. On some level, everyone wants to tell and share his or her personal stories with others. Our social structures just make it hard to forge meaningful conversations with the people in our peripheries. Meeting at a neutral place like a coffee shop is a great way to cross that bridge.

So if there’s ever been someone you don’t know but would like to meet, I challenge you to reach out to him or her. You won’t regret it, though it might be difficult to get started. So hey, if it’s any help, I could be your first random meet-up — just shoot me an email.

I’d only have one request: let’s hold off on the coffee. We can do something else — I’ve had enough caffeine for a while.

Alice Lee is a Wharton junior from Cupertino, Calif. Her email address is leealice@wharton.upenn.edu. Through The Looking Glass appears every other Friday.

Please note All comments are eligible for publication in The Daily Pennsylvanian.