What I learned from over 400 Lyft rides and a self-imposed social experiment

May Pang
May Pang
Jul 15 · 16 min read
Photo by Tim Marshall on Unsplash

I have a question for you.

Yes, you — because this question applies to every single person.

It’s called the 3 am question, and it goes like this.

“It’s 3 am and you find yourself locked out of your house. No locksmiths are available and it’s freezing cold. Who can you call?”

The point of the question isn’t the practicalities of solving the problem (e.g. I live in LA, there are 24-hour locksmiths and it’s not even that cold) or even the likelihood of that problem occurring (e.g. I always have my super secret spare key) — rather, the question is a litmus test of the relationships you have in your life.

This question is essentially asking three questions:

1) Do you have high-quality connections in your life you can rely on?

2) Are these connections current, meaning that you can call them up today and it would not be the first time in 6 months you have called them?

3) Are these connections in close proximity to where you live, and not your childhood friends from your hometown thousands of miles away?

Most people I’ve asked give some variation of:

“Well…….I guess I could ask Brian whom I work with. He lives close. That probably makes the most sense and he’d probably do it.”

The point of the question isn’t who would do it. Most people would do it. It’s about how comfortable you would feel asking that person. What is the strength of this relationship that you wouldn’t worry that it’s a burden on them to respond to your urgent need?

There’s a reason I have thought about creating intimacy in such depth. As an avid traveler who has stayed in many cities for extended periods of time, I ask myself the 3 am question all the time. The quality of my connections in a city is what tips it over from a place I live to a place I call home.

So, when I found myself in yet another new city halfway across the world after moving from Australia to Los Angeles — once again needing to make new friends — I decided to set a challenge for myself to try to really understand how to consistently create intimacy with every person I met.

“But why?” you might ask. Why is intimacy of any kind important?

The Importance of Creating Intimacy in Our Relationships

The dying tell it best

Wouldn’t it be great if our dying selves could go back in time and tell us what the most important things in life should have been? We can’t do that for ourselves, but an Australian palliative nurse gave us insight into the wisdom of others who were dying. In her book, Bonnie Ware shares that of the top five regrets that people had — three involved the lack of intimacy in their relationships.

People (especially men) wished that they hadn’t worked so hard and had invested more in their relationships. They wished that they had stayed in touch with their friends and had given those friendships the effort and time that they deserved. They wished that they had the courage to express themselves and many developed illnesses as a result of not doing so — which brings me to my next point.

It’s literally a life-and-death thing

A meta-study summarizing 148 studies with 308,849 participants concluded that the quality and quantity of individual social relationships has been linked not only to mental health but also to both morbidity and mortality. People in the study were 50% more likely to live longer if they had stronger relationships — even controlling for age, sex, initial health status, cause of death, and follow-up period. There are dozens of other studies correlating loneliness with greater risk of cardiovascular disease, higher susceptibility to sickness, higher blood pressure, and increased pain.

We are programmed to want connection

These findings are unsurprising, as human beings are strongly programmed psychologically to need to belong to a community — something we have known for a long time and that has been described in many book and studies (such as this one). This programming is so strong that in his book, Sebastian Junger describes the irony of how some war veterans feel better in times of war versus peace because of the loss of the incredibly intimate connections of platoon life.

“A human is a social creature” — Aristotle

Life feels better

The mental health benefits of having friends are well documented, but did you know that having strong social relationships has the equivalent effect on your life satisfaction as increasing your income by 150%? This effect is described in a study on life satisfaction by the Gallup World Poll. Other, more commonly-known reasons are that relationships help us deal with stress better and provide comfort.

Created by the author

The impacts of the online world versus real life

This conversation on the importance of creating and maintaining intimacy is even more relevant today, in a world where we confuse Instagram followers or Facebook friends with real friends. This study describes the vastly different impacts the online versus real life friends have on your well-being. Whether we want to or not, the digital world is rapidly changing the way we connect, which makes it even more important for us to be intentional about creating connections with real intimacy.

If you are someone who finds yourself frequently reaching for your phone to find a sense of connection only to feel a sense of emptiness after a dozen left swipes and endless scrolling on feeds, then this article is for you.

Created by the Author

In researching this article, it became apparent to me that the key takeaway in all the studies above is that the quality of relationships matters far more than the quantity of relationships. Relationship intimacy is key.

The Challenge

So when I found myself a new resident of the LA area, I decided to take some proactive steps to create quality relationships.

Armed with a rather generous travel allowance and instilled with the fear of driving through LA traffic, the challenge that I ended up setting for myself was that I would take Lyfts everywhere and try to create an intimate connection within every single ride.

This challenge was especially fun in LA because your Lyft driver could be an aspiring actor trying to make some extra money, a personal trainer to the stars, an inner-city single mom, a Fortune 500 executive, or an immigrant who had won the visa lottery (I encountered all of these). What’s more, because of LA’s unique non-correlation between distance and travel time, a ride could be 3 minutes or 40 minutes.

Lyft drivers come in all shapes and sizes in LA — from 18-year-olds to 70-year-olds, from Nordic skin colors to ebony black and everything in between. And sometimes, to keep me on my toes, I would do a shared ride, just to see if I could create the same intimacy with three, four, or five people in the car. Like Forrest Gump, I never knew what I was going to get. All I knew was that the city was bursting with ambition, rich life stories and, loneliness.

More than four hundred rides later in multiple states, and after extending my challenge to include airplanes, buses, and coffee shops, I learned that creating intimacy is actually easier than we think.

How to Instantly Create Intimacy With Anyone

For most people, the hardest part is how to start. Whether we want to create a familiar community, a friend, or a life partner, most people don’t know how to initiate a connection. So the opportunities pass us by, and we are doomed to the limited social networks of our work and recreational activities — or worse still, the infinite swipes on our phones.

There are thousands of books on how to create romantic intimacy—this isn’t one of them.

This is about how to start a connection and convert any conversation into one where you actually break past the superficial persona of a stranger and discover the real person underneath. It’s about turning the entire world into your community and creating the potential for every person to be your friend.

It turns out, the first step is simply to want to.

Phase 1: Be intentional

Let’s be honest, we’re not always in the mood to interact with people. Sometimes, it takes a little internal pep talk to get us going.

I would often sing the chorus in a song by Zhu called Automatic in my head before I entered a Lyft ride. If you look up the lyrics, you’ll understand why. Doing this set my intentions — it set my mood and how I wanted to show up in that interaction. It reminded me that I wanted to be curious, I wanted to make others feel good, and that I was open. Put yourself in the right mood and be the person someone would want to meet. Have zero expectations and be curious.

This almost never happens without conscious intention. Most of our intimate connections are rife with expectations. Society does not condition us to create random intimacy with strangers, but only with people who fulfill certain roles in our lives — partners, friends, family. These predefined roles also all come with pre-defined expectations. So, we forget to stay curious and allow interactions to play out. Often, the gap between what we expect from them and how they fulfill these roles is what causes the gap in intimacy. People can sense when you have an agenda and it detracts from their ability to open up to you.

So, don’t just talk to the cute guy at your coffee shop (or if you do, do it without expectations) — talk to the old lady who comes in to read every day, talk to the young mother who looks like she could use an adult conversation, talk to the hipster girl drawing in her notebook. You never know who you might meet. I once had a two-hour conversation about concrete and I wasn’t bored for even a second.

Phase 2: Breaking the ice

This is probably the scariest part for most people and the greatest hurdle to overcome. Yes, there will be awkward moments and no, the world will not end. Like exercising a muscle, it also gets much easier over time.

Make eye contact and smile.

That simple? Yes.

Most of us go through our daily lives with unconscious barriers — headphones plugged in that say, “Don’t talk to me”, distant or blank stares that say “I don’t really see you” and more often than not, eyes transfixed on our smartphones that say, “This mindless feed is more interesting than anything or anyone in real life.”

The easiest way to break that first barrier is simply to look up, make eye contact, and smile. Without exception, eye contact is the first point of connection. It’s simple, timeless and extremely underrated. If it’s powerful enough to make you fall in love (as concluded in this famous study over 20 years ago), it’s certainly powerful enough for you to make a friend.

Babies do this all the time and will often hold eye contact with you for a much longer time than adults feel comfortable doing. So, practice with them if it makes you super uncomfortable to start with an adult.

Observe something specific about them then ask a question about it

You smiled, they smiled, now what? One of the easiest ways to open a conversation is to notice something specific about that person and ask a question about it. It can be a book they’re carrying, something they’re wearing, somewhere they’re going, or something they’re looking at.

Created by the author

In time, you might progress to more intimate openers.

“I love your tattoo, what does it mean?”

“You’ve got an interesting look. What’s your heritage?”

I recommend not using the classic opener “How are you?” and I’ll explain more below.

Ask for/offer a favor

Ask for directions, ask for the time, ask for someone to help you reach something, or ask someone to help you hold something for a second. Not only is it a lot less awkward than most other openers, but it’s also actually known to deepen relationships.

There is a famous Benjamin Franklin story of winning over a political rival by asking for a favor, a feat he could not achieve with any amount of kindness. Two of my favorite media on this topic is the 100 days rejection therapy and the Ted Talk called “The Art of Asking” by Amanda Palmer. Watch these if you are skeptical about the magic of asking.

The reverse works as well. You can ask someone who looks lost if they need directions or offer to help a stranger lift something they are struggling with.

Follow up with “feeling” questions versus fact-based questions

After their initial response, it’s best to follow up with a question about how they feel about something instead of a fact-based question.

“Feeling” questions like “What makes you happy?” or “What are you passionate about?” will have a much higher potential of creating intimacy than a fact-based question like “What do you do?”.

If that seems way too awkward in the beginning, ask “What do you love best about <insert city>?”. They will usually fill in the why, and that will give you a pretty good insight into what they love doing.

“My favorite place is this club nearby where a lot of local indie bands play.” “Oh, what kind of music are you passionate about?”

“My favorite place is this park that my dad used to take me to all the time.” “Sounds like your dad is an important person in your life.”

“My favorite place is the beach. I try and get out and surf as much as I can.” “What is it that you love about surfing?”

Here are a few more examples of some easy “feeling” questions:

“What is your favorite music, book, cuisine, movie, etc.?”

“What do you do for fun?”

“Tell me about your culture/where you are from” — Though this is fact-based, it is often linked to strong emotions.

The quicker you can drive the conversation into something they love or hate, the better chance you have at creating intimacy. Favorite books and music also tend to have a deep emotional connection for most people and can often be linked to significant life events.

Don’t ask small talk questions

What you don’t talk about is just as important as what you do talk about. I’ve decided that small talk questions are almost designed to kill intimacy. Aside from the fact that they are almost always fact-based, the biggest problem with common small talk questions is that people have standard responses for them so their response is automatic and they are not engaging in this specific conversation with you.

If you meet a pretty girl in a club, she has likely been asked dozens of times that night, “How’s your night going?” or some other variations of “How are you?”

It’s hard to drive a conversation to somewhere different if the response is simply “Pretty good!”

Instead, try asking them something novel. Challenge yourself to ask them a question they might not have been asked that night. It doesn’t have to be something hard. An example could be:

“What’s been your favorite part of your night?”

“What was your favorite song from the last set?”

“Give me three words that describe your night.”

Phase 3: Connection

Listen. No, really listen.

Listen without trying to formulate a response. Listen without trying to make an impression. Listen to understand their story and what they care about. It’s hard, and anyone who says otherwise is a liar. Most people will reveal things they care about pretty quickly and you should follow their lead. Try making the first three responses you make about the other person and what they just told you.

“Friends are those rare people who ask how we are, and then wait to hear the answer.”― Ed Cunningham

Identify their passion and talk about it

People remember things that create a strong emotional response. They are more likely to engage more deeply with you and remember you if they were talking to you about something they’re passionate about.

If you were listening, you should be able to identify it as most people will pretty quickly reveal their passion. Ask questions about it.

This is my favorite part. Passion is energizing and it’s a joy to listen to. It’ll make your life easier because they can do all the talking but you’ll also find yourself in a more upbeat mood after the conversation.

Be their mirror

Being someone’s mirror means to reflect something meaningful back to them that they may not have been aware of. Typically, it’s to describe more subtle things back to them, to make them see that they are brave, passionate, considerate, determined, etc.

Trying to be a mirror forces you to really pay attention and find something about them you respect. This is a bit of an art but it’s a really powerful thing to do. It says to the person, “Hey, I see you and you are more than you think you are.”

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It may seem disingenuous but it’s not. EVERYONE has something about them that they don’t see. Make them see themselves in a different way.

Make them laugh

If you have a quirky sense of humor, strangers are the best people to be yourself with. They won’t judge and even if they do, it doesn’t matter. So, go ahead, be the sarcastic, funny self you always hear in your own head. They will remember you for it.

Be willing to be vulnerable

Obviously, exercise this one in the right situations and as the conversation calls for. If someone is struggling with loneliness after just moving to a big city, you can express times when you felt the same when you first moved. Having shared emotions or experiences is a very bonding experience.

Phase 4: Conversion

If you’ve successfully made a connection, the next hurdle is to try to continue the relationship outside of the coffee shop, bus or park that you met them at. You may not want to do this with everyone, but here are some tips if you do.

Link the conversation to a location or activity

If someone says they love coffee, ask them what their favorite coffee shop is (location). They will say X coffee shop then you can respond by saying, “Oh, I’ve never been there before! Would you like to go with me?”

If you say, “I love rock climbing” and they have never done that before, you can say, “Oh, I’d be more than happy to take you. I know this great place for beginners.” (activity)

Created by the author

Listen for opportunities

If someone says, “I’ve always wanted to…”, that’s your cue to say, “That sounds like fun! I’d do that with you if you want.”

If someone tells you about their favorite book/song/movie, that’s your cue to say, “Hey, I’d love to read/hear/watch that. Would you mind texting it to me?”

Just ask

By this point, hopefully, they’ve told you their deepest darkest secrets and you can just come right out and say, “Hey, I’ve really enjoyed this conversation. Can we continue it another day?”

Seriously, the worse they can do is say no and it is literally impossible to die of embarrassment.

How Did It Work Out?

First, let me say — I had a blast.

Working through this challenge basically improved every aspect of my life. The ability to create intimacy meant that I could navigate complicated work situations because I could make a cantankerous engineer (that no one else could work with) laugh, or because people would confide in me and tell me the real issue so I could solve it. It meant that I got taken on the best hikes or to the best restaurants, even if I was only in a city for a few days. It meant that I got introduced to the most obscure experiences and learned a lot about other cultures. It meant that people would randomly give me discounts or invite me to their homes.

More importantly, it taught me a lot about myself and how I want to navigate the world.

If you want a more detailed account of all the Lyft drivers, I wrote another article chronicling the people I met.

Still, there are many days when it feels easier to plug in my headphones on the plane. To read my book and forgo eye contact. I had one of these days recently.

I was jet-lagged from a trip back from Asia and was stuck in an airport for 8 hours because of a snowstorm. All I wanted was a coffee and to disappear into my own world. I was searching for a power outlet when two airline employees saw my eyes scanning and asked me what I needed. After establishing that there were no power outlets around, they struck up a conversation.

They did everything I had always tried to do — they made me laugh, they made me feel interesting, they made me feel beautiful, and they made me bare my soul. They surprised me and put me in a good mood despite myself. It reminded me of an article by John P. Weiss where he articulates the immediate joy you can get from connecting with strangers.

After that encounter, I couldn’t help smiling. I knew that somehow, I had attracted that encounter to me. I had created a friendlier world, and it had embraced me.

I hope that you too take the step to connect with the world because there is something magical about knowing deep inside you — that the world is a friendly place. That there is trust, warmth, laughter, and friendship everywhere there are people. That you can fall into the world and it will catch you.

On a side note, I have an idea to host dinner parties filled with random guests who are seeking to connect in a meaningful way. If you can make it to Boulder, Colorado — reach out and you can have a seat at my party! Lyft rides are optional.

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

May Pang

Written by

May Pang

I like being at the intersection of opposites — Rock climber. Corporate executive. Self-experimentor. Traveler. Learner — Come play with me. www.mojomint.com

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

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