Whenever I meet someone for the first time, I ask them the same question.

“Where do you see yourself in five years?”

I get mixed responses. Some people awkwardly make a joke, while others just look confused and give the standard, “Uh, I don’t know…”.

I love the people who jump right in.

Like the young southern entrepreneur who tells me about the family he wants to start with his future wife, or the bright eyed, joyful Christian who excitedly talks about how she wants to open a wellness center.

You really get to know someone when you ask them that question.

I’m always full of questions. It’s a defense mechanism against my natural inclination to be shy. When I was young, I was severely speech delayed, causing years of insecurity and anxiety around public speaking, as well as an occasional stutter.

I’ve devised ways to work around it. I’ve forced myself to be outgoing and social. So much in fact, at times, I worry I seem like I’m trying too hard.

So in a crowded bar, when I’m stuck talking to a guy that I’ve only met a few times, and don’t really know anything about, I just bluntly ask something like:

“So, why do you live in North Carolina?” or “Do you like your job?”

This usually ends with me encouraging them to move out of North Carolina, where they were born and raised, thus afraid to leave. Other times, to quit their job to pursue their passion of making their own surfboards, or moving to Berlin.

I’m a girl that fully encourages the idea that YOLO, although I really hate that acronym.

But other times, it’s not a forced question. It’s out of pure curiosity, or a desire for intimacy.

“Tell me a secret,” I’ve mumbled, multiple times, right before I fell asleep besides someone.

The answers have always been different.

There was the murmured, and slightly lazy, “I can’t think of anything…” with a slight chuckle. Then there was the silly, lighthearted, “I like you,” to which I sleepily contested, that it wasn’t a real secret.

And finally, after being asked the question on multiple occasions, after struggling to think of something he considered to be a “secret”, my boyfriend at the time surprised me.

“You tell me a secret,” he said.

“No one has ever asked me that before,” was my reply, before dozing off.

You really get to know someone when you ask them that question.

I wanted to write this book, if you can even consider it one, because that incessant need to ask questions and get answers has inspired a lot of incredible conversations.

You know that conversation – the one that evolves from a common bond. It can be anything you consider special or sacred. Most of mine start with realizing we’re both from Philadelphia and/or despise American cheese.

Or perhaps something more controversial, like whether or not Hillary Clinton should run for office, or how the other person feels about abortion, or the death penalty.

It’s the conversation that engulfs you into your own little bubble, where it’s just you and this other person, and everything around you has ceased to matter or exist. It seems to go on for hours, when at times, it’s no more than just twenty minutes.

It’s only broken by outside circumstance, such as the flicker of lights, when you realize the bar you’re at is about to close, or the realization you’ve been on the phone for two hours and it’s about to die.

But the conversation is too good. You either head down the street, to a gourmet hot dog place on Fayetteville Street you know is open until three, or you just plug in your phone, and lie on your bed at an incredibly awkward angle, just so you can continue talking for the next three hours.

In my lifetime, I’ve been forced to master the art of conversation. Because over the span of ten years, I’ve had over thirty roommates. I’ve lived and traveled all over the U.S. and internationally.

I’m what my friend Susan calls a free spirit. I’m what my parents refer to as indecisive. I’m the person to call if you want to jump onto a cargo train, or hop a last minute flight to Capri.

I’ve worked at two e-commerce companies, one start-up, and currently, an advertising agency in downtown Durham. I spent a summer in South Jersey waiting tables, another summer interning at a record label in Raleigh, and an entirely separate summer at a radio station in Rochester.
Then there was the time spent hitchhiking around Iceland, where I got picked up by at least 15 people, forcing very interesting, and occasionally drowsy conversations, which is a completely different story, and well… book.