“Who are you going to draw next?” the curious lady asks. Um…I don’t know. Maybe I’ll draw- “-You should draw that lady over there.” She interrupts, pointing to an older woman sitting across from her. “She’s not going to get off for a lot of stations.” The woman with many stations giggles. She and the curious lady are probably friends. I draw her portrait, then turn to see who’s next. I nod to an Indian man sitting next to me. He shakes his head. “I alight at the next station.” Seeing an opportunity, a Chinese tourist sitting behind him hops up: “Please, then, draw me next!” He tries to find a seat across from me, squeezing between commuters. I do my best. I hand it over. His smile grows so big, he asks his wife to come over and take a photo of us together. I can’t stand and go to him—I have too many things. He comes to me instead. There is nowhere for him to sit so he kneels on the floor beside me. His wife snaps a photo of us together, posing with his portrait. His English isn’t good—but his Thank You’s are emphatic.

The lights above the train doors show my stop is coming soon. This train is nothing like I expected Singapore to be. I wasn’t expecting a country that outlaws singing loudly in subways, chewing gum in public, and bringing smelly fruit on the train to have some of the friendliest commuters I’ve ever seen.
I’ve drawn quite some people in this train car now. “Can you draw me too?” I’m surprised to look up and suddenly see an excited university student in front of me. “And do you mind if I film you?” her sister asks, holding up a smartphone and a smile. She’s wearing a yellow pullover dress. They’re a family, with parents in tow. They saw me from a different train car and came over to be drawn.

Sure, I say. No problem. “Oh! But you’ll have to hurry! We’re getting off at Outram Park. That’s the next station!” the student realizes. “Can you draw someone that fast?” No, I can’t. But we work out a plan. When the stop arrives, I get off the train with them. There’s a bench by the tracks. We take a seat, and I can take my time. Because I want to do a good job for this student and her family. Because they look like they really appreciate it. The whole family—mom, dad, daughter, sister—ask me questions:

“Why do you do this for free?”
“How long have you been drawing for?”
“Do you like Singapore? Will you miss it here?”
“What should I do to make an impact on the world?”

…How am I supposed to know that? What am I supposed to answer to that? I don’t know this family, I don’t know the secret to making the world a better place, but this student and her sister ask me life advice anyway. They listen in rapt attention to everything I say. And it is so heartwarming, to see the faith they have in me. Their earnestness, their curiosity, their deep respect in me feel so…good.
We talk for ten minutes. I draw the one university student, then the other. They say a million Thank You’s. They ask for a selfie, all five of us together, grinning wide as the Pacific Ocean.

We part ways.

I told them I wasn’t sure I’d miss Singapore. It’s just a city. But nearly one year later, I find I was wrong. Yes, I do miss Singapore. I miss its commuters, and I miss that beautiful ride in February.

It’s quite late. I sit in the quiet waiting room of the central train station. The walls are painted a dark color and the lamps aren’t all that bright. A few people are trying to sleep behind me, in the time before their train arrives. There’s an older Thai woman and her adult daughter with their large luggage rollers sitting to one side. There’s a man with a scar on his face, one eyelid drooping lower than the other, with hollow cheeks. He’s unfolding a newspaper and reading. I sit down, lay my bag on the seat next to me, and pull out my paper and two pens.

I draw the man. Actually, he’s a little bit scary looking. I’ve learned through drawing seven-thousand-four-hundred-and-eleven people that the order you draw people in is important. Everyone can smile when they get a portrait—but it’s safest to draw the scary looking people last.

Tonight, though, I take a chance. I draw him first. While his scarred face looks like it’s been through a lot, he doesn’t act scary—he’s even reading! My two hands start to move, gliding the ballpoint pens across the surface of the paper, this way, then that.  As I’m about to finish, the man takes note. He looks up from his newspaper. He looks at me, then his watch. He gets up to leave. Just before he can, I hand him his portrait. It’s for you, I say, wearing a smile. It doesn’t cost anything. He looks at it for a while. He puts his things back on his seat. He walks over to me. “Do you think I look friendly?” he asks. There’s no smile on his face. I don’t understand his question. I’ve never been asked this before. Well, I didn’t draw you because you looked friendly, I drew you because you were in front of me. I like to draw people, so I draw everyone. It doesn’t matter what they look like. “I see,” he said. “But…when you drew me…” he thinks over his words, “…did you think I looked friendly?” I still don’t understand his question. I still don’t understand his tone. Does he not like his picture? Did he not want to be drawn? I don’t say yes. I don’t say no. I’m not sure what to say. At my reaction, he looks a bit disappointed. “My friends tell me that I’m not a friendly looking guy. I thought maybe…you thought different.”

Just then I realize what he wanted. Just then I realize that he’s just an ordinary guy with a scary face. Just then I realize that after getting over the shock of being drawn with two hands, his mind started to contemplate something even stranger: that this young artist could think he looked friendly.
 

It all took place in the matter of a few seconds. If there had been more time, or had I not been so tired, I would’ve caught on earlier. I would have told him yes, I thought you looked friendly. But it was too late. He was already gone.

I get onto a Saturday afternoon train to the big city. Experience has taught me that while the elderly don’t pose a threat to me, here in Germany they often feel threatened by me—so I look for a place to sit near immigrants; near youngsters; near people under forty. Finding a seat on a train is like opening a pack of Pokémon cards: you never know what’ll you’ll get to work with. But you work with it. The new parents with mixed kids I had noticed go to sit in some far corner of the train. Before me instead are a group of elderly women. But they’re happy—even full of energy. I get to drawing the happiest one. Whispers begin, and soon smiles too. They are all abuzz with the drawing. They start a conversation with me. By the time I begin on the second elderly lady, even others on the train join in on the conversation. There is such a glow on that short ride. You can never know, until you try.

I have two bags. Together, they weigh 13.6 kg—too heavy for my airline. “It’s OK, I’ll let it through. Just be careful for next time,” the very polite check-in attendant warns me. On the plane, I see why. The overhead lockers are stuffed. I check one section, then another, before I give up. Instead, I try to squeeze my two bags under the seat above me. 13.6 kg—too many souvenirs to fit comfortably in the space before me. “Actually you can put it under this seat here. I don’t think there’s anyone sitting between us.” The girl with the window seat says. I slide out my black, oversized handbag. I push it under the middle chair. A much better fit—no more squeezing. That’s a strange accent…are you American? I ask. No. She’s not. She’s from Singapore. The destination of our aircraft. She’s heading home after a trip to Taiwan.

We start the conversation slowly, talking about food: love-it-or-hate-it dishes and regional delicacies. Soon I notice something strange: she doesn’t love anything or hate anything. She likes ‘garlic cheese’ but doesn’t care much for it. She listens to music but can’t invest the time to know the bands’ names. She watches movies but doesn’t like to think about them afterwards. “For me, because I like a little bit of everything, I don’t really follow anything.”

Sure, I’ve heard “I listen to everything” before. I’ve heard “I really don’t know what I like to do” before. But it’s never true. With sharp skill, the layers of passive I don’t know’s can be trimmed away. I’ve had lots of practice. Most times, I only have a few stops on the train line to get to know someone; to get a feel for that person. I’ve gotten good at cutting the fat off conversations. I’ve gotten good at finding what makes a person smile. But in this case…I trim and trim only to find more fat.

There’s a question I ask that can often reveal a lot about a person: If you could spend the day with your (half your age) self, at the end of the day, what would your younger self be most impressed with about you? She makes a face. “Honestly, I don’t like kids very much. So I’m not sure what I would even tell my younger self. I don’t think my younger self would like me enough to be impressed by anything. So honestly, like, I don’t know. Nothing, I guess.” I’m starting to realize that maybe this isn’t just a defense. Maybe it’s not that she’s too embarrassed to talk about what drives her. Maybe, this girl from Singapore with well-shaped eyebrows really has no defining interests; really has never let herself develop a passion; really has no shape, conforming to the container she’s in: this girl is like water.

Her brother, I learn, is more like me. He has dreams and ambitions. He enters a conversation knowing what he wants. He talks of deep things. She does not. “All my conversations are really surface, because, I guess I think that nobody really cares about my opinion anyway.”

I like to stare into the depths of people’s souls—I like to know what makes them. When I see a face, I imagine what makes it smile; what makes it frown, cry, grow sad, look puzzled; what makes it laugh. The week before, I visited a crossing in Shibuya with literally a river of people. Thousands of bodies, moving in and out with the flow of traffic lights. Thousands of faces. I looked at as many as I could. I stared into their eyes. I tried to see their souls. I tried to imagine their families. I tried to imagine how they grew up and who they were. I didn’t want to see them as water. I didn’t want to dehumanize them. But this Singaporean girl on the plane, who likes ‘garlic cheese’ but doesn’t care much for it, this girl who watches ’11 ways you know you’re really Singaporean’ but doesn’t particularly enjoy it, this girl with well-shaped eyebrows who sums herself up as a ‘squiggle,’ she may well be water. 

​Do you mind if I draw a few people? I never know what kind of attention I’ll attract through these drawings. So if I’m with a friend, I ask before I begin to draw, as a courtesy. “Actually, I’m really curious to see what people’s reactions will be. Is there a particular place we should sit?”
 
The prospects look decent. It’s a late night, so there are still available seats on this downtown Hibiya line. We have five or six stops, around fifteen minutes. —That is absolutely right! It was Hibiya line where all the wonderful things happened!! (This is a bit of a unique occasion; since my friend was there too, I asked him to look over my draft of this story. I put his comments in green)
His stop is one before mine. “So…who are you thinking about drawing? The girl in front of us? Or…” I think I’ll draw this guy on our left. He has a head of black hair that is combed forward at the top. He is probably in his early thirties. He has strong eyebrows. His collar is raised quite high, covering his chin and obscuring his jaw. I draw what I see. Of course, the gentleman notices. But this is Tokyo. This isn’t something you do here. So the gentleman looks away. He continues reading his book. And then it’s done. I put my pens down, I snap a photo, put my camera back in my pocket. Sumimasen, I say, Anata no kaku desu. Kore wa purezento desu. (Excuse me, it’s your portrait. This is a present).

I don’t have a smart phone, but I have about thirty sheets of really special, not ordinary, thick, light green paper, and two pencils. I know what to do with them. I draw everyone around me during my five hour layover: a young Alaskan couple making their way to Italy. A Russian family with a young girl, hair braided and legs swinging. An Indian man with a great big mustache. An old British couple. A French brother and sister, who try to teach me their language. And with each person I draw, my stack of special lime-green paper gets just a little thinner.

I draw two families travelling with about six kids. They’re on their way to a snowboarding exhibition. They want to pay me. I explain what I really need is more paper. “Sorry, we don’t have any.” The stack gets lower. I’ve got four, three, two, finally one sheet left. I look left, then right. I shake out my hands (it’s important to take good care not to overwork them). I start on my final portrait. “-Don’t worry!” a young girl says, in the most adorable British accent. “Paper is on its way!” Her parents and a few of the kids were dispatched to find me more paper. They head down the terminal, asking workers along the way. Soon I’m all done with this portrait. I hand it over. One of the little ones assures me: “they’re going to bring the paper soon.” Such a cute accent.

​And the paper does come. About twenty sheets of everyday, ordinary, A4 printer paper. With it, I am able to draw until my plane takes off. It’s not the paper that’s special. It’s what I can do with it. When I land in Munich, and have to take my train back to my apartment, I run out again. I’m always running out of paper. But there are always more people. There are always more smiles to create. So on the S-bahn heading home, I use the back of my boarding pass to draw just one more person. Shuffling through my folder, I find my itinerary: even just *one more* person. It turns out, it was his birthday.
Forty-six people in one journey. I am always running out of paper.

Portrait number one.

Who was number one? I don’t know. I simply can’t remember. If I were to guess, I would say it was in a Communications class in the top floor of a building in the Mojave Desert. But that’s only a guess. In reality, I have no memory of who portrait number one, ten, one hundred, or one thousand were. I don’t remember people by the number I write on their portrait. I remember them because they were interesting—because their personality is one in one thousand (sometimes literally!). And so today I write about a different portrait number one.

I was travelling from Berlin to Munich. I needed to stop somewhere along the way. My first time in Germany, I had only partly planned my trip. Where to next? I trace my finger on one of the giant maps in the Berlin train station. Kassel…Rodenburg…Ulm…I’ve never heard of any of these cities. Dusseldorf! I’ve heard of that! I decide to stop there. I note down the next departure time. Before long I find a seat on the high-speed train: ICE, Inter-City Express. I get my luggage in order. I settle in, find a seat, pull out a white sheet of paper, two pencils, and get started doing what I always do.

He’s a mellow looking guy, still studying in university. He’s got a black jacket with the zipper only partly fastened. “Are you American?” Yes. I didn’t even need to open my mouth. I don’t know how he can tell so easily. Maybe it’s the drawing strangers part. “Where are you heading to?” Dusseldorf. “Why?” Because it’s the only city I’ve heard of between Berlin and Munich. “Really?” chimed in another passenger. She’s a bit ‘goth.’ She’s been paying attention ever since I started drawing the student. “If you’re only visiting Dusseldorf for that, you really need to visit Köln instead.” “She’s right, you know…” the student adds, “the people in Köln are really nice and down to earth. The people in Dusseldorf on the other hand…” his face wrinkles, “…are too schickimicki.” It means snooty, I learn. “Trust me, if you can only visit one city in Germany, Köln is the best one to visit.” A third rider chimes in.

It’s this third rider who was curious enough, brave enough, crazy enough, to take a look at what I was doing with my hands. I had drawn one, two, all three riders already. Of course, with both hands. We talked about that too. And so, after a few stops, and a lot of questions, she asks if she can have a piece of paper. She asks if she can borrow my two pencils. She gets up and finds a seat facing me. She places the sheet of drawing paper on the small table between us. She holds the pencils tight. She looks up at me, steady. “OK, I’m gonna try this too.” Pencils hit paper. One hand mirrors the other: left right, right left. Her eyebrows knit: this is hard. Just let your left follow your right. Don’t mirror. I advise. She nods. She tries again: left left, right right. It’s faster this time. The wrinkles dissolve from her forehead. “You’re right, this is easier!”

Everybody is watching. She apologizes every so often: “I’m sorry this won’t be as fast as yours!” This one isn’t done in three minutes. But we all look on as slowly, my face comes to be recognizable on the paper, here on the table we share. She holds it up and stares: first at me, then the paper, then me, then the paper. “It’s done!” she exclaims, before snapping a photo. “Here you go! It’s my gift to you, now.” She is so proud. I hold the paper in my hands. It was a good job. She matched my format: I see her signature, the date, and at the top left, something special: a number one. I am portrait number one.

​I hope she drew a portrait number two. And I hope by now, she’s had the joy of marking down a one-hundred, five-hundred, or even a one-thousand, on the corner of her portraits too.

A dozen tiny pieces of paper flutter to the ground. They fall at my feet. They fall at his feet; his girlfriend’s. “What did you think you were doing, huh?” He shifts around in his blue plastic seat. I was only drawing. “Yeah, but why’d you draw me? Why’d you draw me, huh?” Because I just started drawing people. I want to draw one-hundred people, and I’m really close. You were number ninety-two. I only need eight more to draw one-hundred. “Yeah, well, you should’ve asked. It’s rude. You’re rude, man. This guy, this guy, he tried to draw me. He didn’t ask, he just started drawing me. That’s rude, right?” The gentleman is nervous, but angry—two emotions that don’t normally go together. He looks to others in the bus for confirmation. “…hey, I thought it was kinda cool…” his girlfriend said. She doesn’t like that he had torn his unfinished portrait into all those pieces. “Yeah, well, you’re lucky we’re in a bus, man. I might just get up and beat your ass. Drawing me? This guy was trying to draw me. That’s rude. It’s really rude. You need to ask people before you just go around drawing them. That’s rude, man.”

The back of the bus is quiet now. I don’t want the situation to escalate, and I really don’t want to get hurt. So I tell him I’ll ask next time. Looking at the tiny shreds of his portrait on the floor of the rocking bus, I start thinking maybe he was right. Maybe I need to ask everyone before I draw them. Maybe somehow what I’m doing is rude. But when I ask…people say no. They don’t know why you’re asking; if you’ll want something in return; why you chose to ask them. It’s just too weird and random—so people just say…no. It’ll take me a lot longer to reach one-hundred this way.

I get off the bus. I have to wait for another. A friend of mine has taken the same bus from school. He had heard the noise. “What was that all about on the bus?” I explain what happened. He can tell it affected me. “Don’t worry about it. Look, that’s one guy in what, ninety people you’ve drawn? I think it’s pretty cool that you draw people anyway. Look, if you want to draw somebody, draw them. Don’t worry about this one person. He probably just got out of prison and was already in trouble again. Just don’t draw people that look like ex-cons, and you’ll be alright.” Others, waiting at the bus stop, had seen the whole thing play out too. They were warm and encouraging. “Yeah, he just crazy! Just keep doing yo’ thing, baby.” I was still a bit shaken, a bit depressed. But I drew a few of them too: ninety-three, ninety-four, ninety-five…

That week I reached my goal of one-hundred portraits.

That was a few years ago. Today I reached portrait number five-thousand-and-twenty-five. Five thousand…I cannot imagine how different life would be had I stopped at ninety-two. Sometimes, the coolest things in life grow slowly, randomly, without a real reason. A love of music, fashion, cooking, writing, comics, drawing: these things need time to mature. They need time to become rewarding. With enough time, they flourish and grow into some really cool things.

At the I House, my dorm in college, I grew this hobby. I drew every one of the six-hundred residents there, two years in a row. Six-hundred students from Lebanon, China, Israel, Argentina, Guinea, Finland, Kenya—eighty different countries. And through drawing all of them, I got to meet and talk with each of them. I got to learn about the lives of people from every corner of the Earth. I had an excuse: I was just drawing their portraits. “I want to draw six-hundred people at this dorm, and I’m really close—you’re number five-hundred-and-ninety-two.” I met many friends I never would have had this way. I wrote a few of them just today.

I still draw people on buses. I still draw people on trains. I still remember the face of a homeless man on a subway with a great big beard, who grinned from ear to ear when he saw his portrait. He folded it neatly and kept it in his coat pocket. I still remember the smiles and fascination of three school boys who I drew one by one on a train while commuting. They compared their portraits and talked with cheerful voices as they got off the train. I still remember the stories and the struggles I’ve learned from others I’ve drawn.

No, I don’t always ask first. I often don’t ask first. Even so, every now and then, I get a message in my inbox from one of these strangers. Here’s one I especially like:

This person wrote me two months after her portrait was drawn. Some write me the same day. Others six-months after. But I’ve been lucky enough to see a lot of smiles. A few thousand more than if I had stopped with number ninety-two.

…

A bit of advice for you out there getting started with candid portraits:

1. Draw old people first. They know they have no reason to be worried. If there are no elderly around, draw women, draw children, or draw ‘geeks’ next. Once everyone understands what you’re doing, they relax. Then you can draw anyone, sometimes even those who look like ‘ex-cons.’
2. If someone asks if you’re drawing them, be honest. Say yes. Let them know you don’t want money. Let them know you’ll give them their portrait when you’re finished. The more they know, the less they worry.
3. Be kind and respectful. If you mean well, most people will mean you well.
4. Draw only when you’re in a public place with many people. It’s safer.

Those are just a few rules I learned. I don’t need to follow some of them anymore. I draw with both hands now—it’s so out-of-the-ordinary, most are too distracted to think of anything else (one high schooler spent three minutes alternating between “wow” and “voll wow,” German for “totally wow”). I’ve seen a lot of mouths hanging open, a lot of speechless people. With time, you get better talking with people. You can put them at ease more quickly and even get some good conversations going. Remember that some things take time. Never let one bad experience—or two—stop you from starting something new.

I’m always running out of paper. Today I’m on the brink. I’m on a train in Munich. I just landed, my first day back in Germany. So I can continue drawing people, a kind passenger gives me a dozen more sheets. A small miracle. I can’t ask for more than that.

I draw a crying little girl who soon becomes a smiling little girl. I draw her sister, her dad, her uncle, her mom, and basically the whole family. I draw a Frenchman. I draw a German woman who lives in England. We get a good conversation going, half the train car taking part. A real conversation. I like curious people: they ask good questions. We talk about learning languages. I mention how wonderful it is to practice with native speakers so easily, when I can start a conversation through a portrait. German, Spanish, and Japanese especially, I mention, since it’s so hard for me to find. Not thirty seconds later does a young Asian woman board the train, and grab a seat directly opposite me. I had already drawn everyone else on the train, so of course, my two hands start to drawing her picture now. She watches her form start to take shape on the page: first her dark hair, parting at the front, falling at the temples. Then eyebrows, wide eyes looking, and slowly, a smile forms from a thousand pencil strokes. I ask her name in German: “Wie heißt du?” “Yumiko,” she replies. Yumiko? A Japanese name! What a coincidence! Immediately I break into what little Japanese I know. Yumiko, the stranger on the train, is instantly surprised. Here is an American on a German train drawing her portrait with both hands, while speaking (broken) Japanese!

I have a very small Japanese vocabulary. I know a few stock phrases. I can build new sentences with a few sentence types in my tool box, and the words demo (although), dakara (therefore), and to (and) go a really long way to me getting the most out of what I have. That’s a long way to say: you have to be very patient to speak with me in Japanese. You have to really want to communicate.

She does. We exhaust my store of stock phrases. We expand to new subjects. We speak of travelling. We speak of music (I’m a big fan of Japanese music, so that’s always a go-to topic for me). We speak of friends and school. When I don’t know a word, we search and find an English word we know in common. When we can’t find one of those, we find a German one. Even when all words fail us, we push forward to understand each other, without them. When words and phrases can’t be recalled, even the silence holds meaning. We just smile, and enjoy being two people on a train, honestly enjoying each other’s presence. It isn’t so much that we enjoy what we’re communicating. It’s that we enjoy communicating. It’s a moment of real, strong, deep connection—and plenty of grins.

My stop passes. I do not care. The next stop, too, comes and goes. I have a day-ticket, so twenty minutes out of my way is just twenty minutes more time to share. Twenty minutes more connection. Twenty more minutes to learn from this person in front of me. It doesn’t feel like she’s Japanese or I’m American or like we’re meeting in Germany. She could be from Lebanon or Italy or Brazil or Iceland and it would change nothing. We’re just there. No assumptions, no judgements. It’s…a ‘click.’ I’ve seen it a few times before. Once every two-hundred, three-hundred, portraits or so. These moments are always fleeting, I’ve found, so I want to savor this one while it lasts. We always part ways. I hardly ever hear from these people again. But we are both left with a memory, the knowledge that two human beings, perhaps from different countries, religions, languages, can sit down together and honestly want to learn from each other. That they can honestly enjoy each other’s presence. A small miracle, us meeting on a train. I can’t ask for more than that.