Meeting Chelsea: How I Approached One of My Heroes on the Street

She had already passed me on the street by the time I realized who she was.

“Gotta go,” I blurted to my friend, and ended the call. It was a little brusque, but I knew she’d understand later.

“Excuse me,” I called out, loudly enough to grab her attention but gently enough to not come across as some aggro dude hollering at her on the sidewalk. She stopped and turned her head.

“Hey,” I offered. “Sorry to bother you, but did you tell a story at John’s dinner party a few nights back about being on the boat ride from hell?”

I couldn’t stop thinking about Chelsea’s story since that night. It was funny and embarrassing and awesome. She had stood up at John’s event and told us about this time she got trapped on a yacht with food poisoning, which was gross and bold and hilarious at the same time. Along the way, she sprinkled in a few details about her work projects, which were so enviable they basically made me want to be a male version of her. I’m not going to lie: She was kind of intimidating.

“Yeah, I did,” she said. She was facing me now, but glancing back to the restaurant down the block. Clearly on her way to meet someone.

“I just wanted to tell you how much I loved it. John and I work together. A bunch of us sat around talking about that story for a while after you left. Too funny.”

“Oh. Wow. That’s so sweet. Thank you for telling me that,” she smiled.

“Of course. I have to run, but I’m really glad I saw you. You going to John’s thing next month?”

“Actually, no. I live in New York.”

Bummer. So this was it.

“Well, have a great trip back and I hope we cross paths again some day. I need to hear some more Chelsea stories.”

“What’s your name?” she asked.

“Gavin.”

“I’m Chelsea.”

We shake hands. And then we part ways.

When I go home, I find Chelsea on Facebook and send her a quick message. “I’m the guy who ran into you on Fountain today. Very cool to see you again.” I don’t send her a friend request. I just take her back to that moment.

A few days later, she responds.

And then she adds me on Facebook.

And now we’re friends.

This little anecdote seemed so mundane, so random, that at first I didn’t even think about sharing it with you guys. But since that night, I’ve developed a really cool friendship with Chelsea, and I realized that more went into making that interaction a success than I consciously realized. To me, small moments like this capture the spirit of what we teach at The Art of Charm.

Because what we’re sharing here is about so much more than just the art of approaching. It’s really a philosophy of grabbing life as it happens and making it work to our advantage, in a fun, playful, meaningful way, often against the odds. It’s a process of rewiring our own beliefs about what’s possible, and rewriting social situations to capitalize on those beliefs.

Like getting over the idea that you can’t approach a stranger on the street, and reorienting that moment to make a new friend.

Which is exactly what happened with Chelsea.

In that split-second moment, I confronted two totally different choices: Continue my phone call and let her walk by, or simply stop and say, “Hey.”

My first instinct was to just continue my call. It would have been much easier to keep moving along and not break the pattern. Like most people, that’s my default setting.

But in taking the chance—that’s where the magic happens. So I did.

We can’t plan for those moments. They come to us. It’s our job to be ready for them, and to do the best we can.

“As Estha stirred the thick jam he thought Two Thoughts and the Two Thoughts he thought were these: a) Anything can happen to anyone. and b) It is best to be prepared.”

— Arundhati Roy, The God of Small Things

So if we had to break it down, what happened on that sidewalk?

Well, I don’t think we can reduce the magic of a spontaneous conversation to a set of stringent principles. That’s not really the point. But there was definitely a logic and a science to that exchange, so let’s isolate some of the principles that helped make the most of that moment.

As far as I can tell, here’s what went down.

First, the world brought us together. Most good things happen that way. I could never have orchestrated that scenario. The world did it for me. It’s important to notice when the world does that. The biggest part of taking a chance is recognizing when one has been given to you.

And yet, if you know anything about the art of approaching, you know that the dynamics were completely against me. She was walking the opposite direction, already late to meet someone. She didn’t know who I was. I was on the phone. None of this was conducive to striking up a conversation. In fact, a lot of experts would say to never approach someone under these conditions. The hurdles are just too great.

But something told me it was possible. And that’s part of the equation too: using your instinct. In this case, my instinct told me to go for it.

That was my experience. But what about hers? I knew a decent amount about this woman already, but she didn’t know me at all. As far as she’s concerned, I’m just some guy on the street. I had to call that out.

“Excuse me—hey—sorry to bother you, but…”

And that’s how I let her adjust to me before I jumped in. That’s a crucial step: to acknowledge the other person’s experience of you. It seems silly, but you have to let people know you’re not a psycho. Especially in a city like Los Angeles.

But that’s not enough. I couldn’t just not be weird. I had to also not be a total stranger. What did we have in common?

The dinner party. John. Her story.

More than enough.

So I told her where I saw her. I mentioned John. I complimented her story.

By sharing those things, we already knew each other. We just hadn’t met.

The compliment on her story, by the way, was real. It had to be. Smart people can smell falsity from a mile away. Authenticity is essential. If I hated her story, I wouldn’t have given the compliment. That’s important, too: Committing to honesty.

That’s when she asked me for my name. Interesting. That speaks volumes: You’re all right. You’re cool. I’d like to know you too. It signals a kindness and a curiosity that tell me we’re on the same frequency now. We’re both interested in talking to each other.

But even then—even after all that good stuff—it still could have been just a nice moment on the sidewalk. She might have gotten on the plane to New York thinking, “Hey, that was really nice.”

Which is great. If our conversation had ended there, that would have been superb. We deserve to be recognized. Sometimes a conversation is worthwhile for its own sake.

But these days, moments don’t have to end. With the right etiquette, Facebook is our best friend. That’s the glue that turned our conversation into a friendship.

In summary, here’s what I took away from my sidewalk exchange. Maybe it’ll come in handy the next time you want to walk up to an interesting stranger.

  1. Listen to the universe when it serves you up an opportunity. Really listen. It usually means you should take it. At the very least, you’ll learn something about yourself.
  2. Recognize that relationships are actually being built before and after you physically meet someone. There were three steps to meeting Chelsea: The dinner party, the moment on the sidewalk, and Facebook. All three were necessary.
  3. Don’t be afraid to break social norms in a polite and respectful way. Worst-case scenario: You come across as a little random. Best-case scenario: You put yourself in a situation in which you can shine.
  4. Textbook theory says not to approach people when the odds are against you. It’s definitely harder, but certainly not impossible. Done right, it can actually work even better. It requires confidence and self-awareness to take that risk. That’s the true art of approaching.
  5. Establish common ground as soon as possible. Jump over the barriers. Don’t feel the need to overly ingratiate yourself, but take a moment to signal that you’re part of the same tribe. On some deep evolutionary level, people need to know you’re cool. It helps if you are already somehow connected, but “tribes” can be built around humor, kindness, interests, and even a distinct lack of creepiness.
  6. Only pay real compliments. Commit to never giving false ones. Anything else is hollow or manipulative.
  7. Pay attention to body language and conversational cues. The most interesting things go unsaid.
  8. Finally, follow up. That is all. It’s the easiest part of an exchange, and yet most people fail to do it.

Because a great moment doesn’t have to end. It can actually be the beginning of something spectacular.

And it all begins with taking a chance.

For more on the art of approaching, be sure to explore our blog and subscribe to The Art of Charm Podcast.


in Approaching A Woman