Talks in Thailand: Ms. A the Ladyboy

We rode on her scooter past the ancient walls of old Chiang Mai city from the hostel where she works.

When we got to the restaurant, I felt like everyone was looking at us. Even now, I’m not sure if this was real or just in my head. She had make up, a short black dress, and high heels, but there was still something masculine about her.

She had gotten dressed up for me. She was still putting on her makeup when I got to her hostel at 7:15, which is when she finishes work.

“You’re so cute,” she had said when I arrived.

“Thanks,” my discomfort levels were maxed out. I had never talked to someone like her before, but I was trying to play it cool. Everything about this felt like a date.

That shouldn’t be too surprising, because I met Ms. A on a dating app. I had been using the app to try to find a date in Thailand, cautiously examining every girl’s shoulders and chin to see if she might be a ladyboy before I sent her a message.

Forgive me a moment while I salute my own flag, but I do extremely well with online dating. I’m an introvert, a writer, and a nerd. It’s written in my DNA to excel at e-dating. The best way to do it, as a guy, is to find one good opening line, and mass send it to every girl.

Depending on the line and your profile, somewhere between 20% and 40% will respond. Talk for a while with those who respond, then focus on one after that. I know this isn’t romantic, but it really is the best way to do it.

It’s like applying to a job. You don’t try to snipe your dream job. You shoot your resume out like buckshot and take the best target you hit. I’m not good at metaphors, but in this one the target is the girl and the buckshot is your dorky opening line.

And if you’re a girl using a dating app, the best way to do it is to open the app and scroll through the hundreds of messages you receive every day, trying to find a guy that doesn’t set off your creep alarm. I don’t know, I’ve never been a girl on a dating app.

Anyhow, that all changed once I decided to continue my interview series in Thailand. Ladyboys have become an unintentional cultural icon of this country, so my goal on the dating app flipped. I started seeking ladyboys. I loaded up with the buckshot of a new opening line for them.

I had no idea what to expect once they started talking to me. I’ve had no direct exposure to transgender people, as far as I know. And every movie I’ve seen set in Thailand has at least one part with a ladyboy preying on an unaware hetero man, like a spider entangling its victim in a web of confusing genitals

What I found was the opposite. Every ladyboy I talked to was very upfront, making sure I understood she was a ladyboy even if I hadn’t asked. In return, I made sure they knew I wanted an interview, not a date. Some weren’t interested, some were busy. Finally, I found Ms. A, who said yes.

But as I waited for her to finish her make up, I realized our roles had swapped. It didn’t matter how many times I told her I only wanted an interview. She had become the one firing the buckshot and I had become the target. I wasn’t sure how I felt about this role.


Now, as we walked into the restaurant, everyone seemed to watch us. The most uncomfortable part was that I couldn’t figure out why it made me uncomfortable. I was there to have dinner and talk to a person. What’s more normal than that?

Once we sat down, I told her, “I want to start by saying that I don’t know anything about… this. I have no experience. So if I say something stupid, I’m really sorry.”

I wasn’t just being polite. Transgenderism is a hot topic in America these days, from Caitlin Jenner to Target’s bathroom policy. But I have never once spoken to a trans person.

My complete lack of transgender understanding is both why I needed to do this interview and why I needed to preemptively apologize for any embarrassing questions I was about to ask. It’s one thing to support their rights and try to use the correct terminology, but it’s another thing to sit across the table and listen.

“It’s fine. Ask me anything.” she said.

I asked her if the phrase “ladyboy” is derogatory. I thought it might be better to say “transgender.”

She told me there’s nothing bad about the phrase “ladyboy.” She explained that she’s not transgender.

“Why?” I asked. “A man gets an operation to become like a woman. Isn’t that transgender?”

”Ladyboy still has… I mean, a ladyboy had the operation to get tits. But below? Not yet.”

”Do you want the full operation eventually?”

”No. I heard they can’t orgasm, so I’m not interested.”

It got personal very quickly. I should have known we’d talk about the nuts and bolts of this subject eventually, but I still felt self-conscious discussing it in the middle of a cozy restaurant in Chiang Mai. We picked at marinated beef and sauteed zucchini while we talked about transgender genitalia.

That’s really what it’s about. These genitals or those ones, and why some people go to such extremes to get the other ones.


“ How old were you when you got the operation?”

”Seventeen,” she said.

Ms. A was twenty-eight at the time of the interview, meaning she’d had eleven years to grow comfortable in her new body. She told me that while many ladyboys take hormone pills to help their bodies continue the transformation, she doesn’t need to.

“See? My body is already soft like a woman’s,” she said as she extended her arm towards me. I touched it and it was soft, I suppose. She smiled. I pulled my hand back.

“How long had you known you wanted to get the operation?”

”Since I was a kid.”

”And how did you know this was right for you?”

She shrugged her shoulders and said, “I don’t know. It’s hormones, right?”

We hadn’t even finished appetizers and I already threw out my first stupid question. Of course she can’t answer that question. The old argument came to mind of, “When did you decide to be a straight man?” I didn’t. I guess that was all hormones too.

It is all hormones, isn’t it? I can’t say for sure. I’ve never experienced being anything other than a white, hetero male. But if it’s all hormones, why are there so many ladyboys in Thailand and so few in Korea? Are the Korean transgenders repressed or are the Thai boys encouraged? I can’t answer these questions through my own experience, so I have to take it on the faith of others. I’ve never been good at that.

She continued, “All my life, I had wanted to be a beautiful woman. So I found a solution.”

She told me to put down my notepad and eat like a normal person so my food didn’t go cold and my beer didn’t go warm. As we ate and talked, she asked me, “You’ve really never done anything with a ladyboy?”

She sounded surprised when I said I hadn’t. I reminded her that I’m straight, but she responded that all her ex-boyfriends were straight. Now I was the one sounding surprised. I was pretty sure being a straight male meant you weren’t into other people who had male parts.

She said, “I just wish you were open to having a new experience with me. What happens in Thailand, stays in Thailand, you know?”

*                                         *                                        *

“Why do you think there are so many ladyboys in Thailand? I was in Korea before coming here, and I never even heard about ladyboys there.” I asked.

She thought for a moment, then said, “Because in Thailand, we don’t care. We respect people. If you’re a good person, we don’t care.”

I don’t have much experience in Thailand yet, but I agree with that so far. People don’t seem worried about labeling others here.

“Is there a ladyboy community out here?” I asked.

“Yes, I have a group of ladyboy friends.”

This was the question I was most excited about when I was planning for the interview. I imagined there might be an entire ladyboy subculture, complete with it’s own cliques and personality. I asked her how she met her ladyboy friends. She said through other friends or at a bar. I asked what they do when they meet. She said go shopping, watch a movie, or have some drinks.

I realized this was stupid question number two. Her group of ladyboy friends are just a group of friends, and they meet up to do friend stuff.

She added, “But usually I don’t like other ladyboys.”

“You don’t like them? Why?”

“They steal. They work in the bar.”

“What does working in a bar mean?” I asked.


I had a suspicion that’s what she meant. The prostitution business usually runs from bars out here in Thailand. You can order a drink, and if you see a waitress you like I guess you can have her too.

The Thai baht is the currency here. A typical meal is about sixty baht and you can find rent for as low as three thousand baht a month. In USD, sixty baht is just under two dollars and three thousand baht is about eighty five bucks. A buck goes a long way out here. A steady stream of lonely, male tourists with fistfuls of baht might seem like an opportunity for a poor boy with no options.

I knew about the prostitution, but I was surprised that stealing was the first thing she said about other ladyboys. It’s an answer I never would have imagined and I wanted to know why.

“Why do they steal? Is it difficult for ladyboys to find work?”

“Normal jobs don’t take ladyboys. They have to find jobs that accept them. They can’t even work at 7-11.” She added, “I’m lucky. My hostel accepts me.”

”I thought you said Thai people don’t care. They accept ladyboys, right?”

”No no,” she said. “They accept ladyboy for normal life. But for work we have to be professional.”

She explained that Thai culture is still very conservative, despite how many ladyboys there are. They only accept people as men or women, nothing else.

She told me that ladyboys cut their hair short and try to look masculine when they go job hunting. Once they’ve been with a company for years, they might be accepted to continue working as a ladyboy. Or they might not be.

Thailand is already a poor country where it’s difficult to find a job that pays the bills. That job market becomes even smaller for ladyboys.

We finished our meal and got up to pay. As we walked out of the restaurant, I thanked her again for talking with me. I told her I had asked another ladyboy to have this conversation, but she had said no. She had said she doesn’t like to talk about it because she wants to think of herself as a real woman.

After Ms. A heard that, she said, “Yeah, we want to think like we are a woman. But it’s true. I am a ladyboy.”



Ms. A kept hitting on me through text for a week after the interview, saying things I won’t print here because my parents read my blog. Every time she did, I told her very clearly that I wasn’t interested.

I also said that I was sorry every time I explained my lack of interest. I know I didn’t do anything wrong, but I really felt sorry. Is this how women feel when they reject a guy, or does that feeling numb after the hundredth time?

I realized there’s so many more questions I should have asked, but didn’t. I knew I should do a follow up interview, but I felt uncomfortable talking to her because she couldn’t get over seeing me as a target.

I thought of girls in my past who had stopped talking to me after I flirted with them. At the time, I thought they should feel flattered because of my infatuation. But now I understood. It was impossible to have a real conversation because Ms. A always rolled the conversation back to attempted seduction, no matter how many times I told her I wasn’t interested.

It made me wonder if I’m just as annoying when I’m going after a girl. I’d like to think I’m not, but I really have no idea. Love may be blind, but hormones throw dirt in your eye. In the moment, I can’t objectively see my own behavior well enough to judge.

It’s that instinctive, animal like drive. That’s the drive that make me into an idiot when I like a girl. I would probably choose to turn it off so I could think straight, but I can’t control it.

That’s also the drive that makes Ms. A go so wild for men that she wants to radically change her body. She can’t control it either. I imagine if she had a choice, she’d turn it off too so she didn’t have to become such a social oddity that people gawk at and businesses won’t hire.

Eventually I decided to just ask her one more question through text. “What are your plans for the future?”

“To find someone I love and stay together forever,” she said.

We go to such lengths to be wanted by those we want.

Pictures: Melissa Beth Rose 
Words: Michael Smit

Authors note 11/5/2016: 

A few friends who read this post messaged me about part of it being incorrect and/or offensive. Specifically this line, “That’s also the drive that makes Ms. A go so wild for men that she wants to radically change her body. “
My purpose with that line was to make a connection with the previous paragraph about how my own sexual drive turns me into an idiot. But the line also implies that Ms. A’s attraction to men played at least a part in making her want to look like a woman.
In reality, she probably wanted to look like a woman to feel comfortable with herself, to feel on the outside the way she feels on the inside.
I don’t know if anyone was offended by any inaccuracies in this post. I hope not. My blog is my expression on how I see the world. That comes with the good and the bad, the revelations and the inaccuracies. Please do not read my blog as a scientific resource. I couldn’t even explain to you the chemistry and processes going on in my own heterosexual, male brain. Much less a transgender female brain.
Going in, I knew I was certain to get some things wrong. But like I said in the post… it’s one thing to use support their rights and use the correct terminology, it’s another thing to sit down and listen. I wanted to do the later. I probably got some things right and some things wrong, but I’m happy with the result. At the end fo the day, I now have a fuller, more human view of Ms. A. Hopefully I gave some of that view to you.
Furthermore, if you ever read something in my blog that you disagree with or think is factually wrong, leave a comment and let me know. I love the discussion and the only way we grow is by challenging the things we think are true.
Anyhow, the point is that I’m going to try to do a follow up interview to this with a transgender person from Los Angeles, and hopefully we’ll all learn more. That’ll be rad.

On Five Months in Thailand

I never know how to summarize long stays overseas, but I feel like I should say something. I planned to stay for a month, maybe two if things were going well. I ended up staying for five.

It seemed like a long time while I was there. I started calling it home. But now I’m back in the States, watching college football and drinking craft beer. It’s only been a few days, but the memories of Thailand feel like a dream you know you had but can’t remember.

I’ll start with the small details and see what kind of memories those spark.

myCat is a phone service provider in Thailand. I was at their store renewing my monthly phone plan one day. I watched out the window while I waited. It looked across a busy intersection. A large, open bed truck drove by transporting an adult elephant.

There’s a fruit called “durian” that’s popular throughout Southeast Asia. It has a uniquely strong odor which smells exactly like a fart. My local grocery store had a durian display at the front all summer. The whole store smelled like a fart.


At night, I heard an eerie sound. It was like a frog’s croak, but not as deep. I eventually learned it was a gecko. I heard it every night, but never saw it.

Scooters are everywhere in Thailand. On my first day, I rented a scooter so I could drive around and look for an apartment. I had never driven one before. The building I rented from opened onto the highway, so I didn’t have space to test the acceleration and turning.

I strapped my helmet on tight, waited for an opening in the heavy traffic, then gunned it. I ran straight into the median and had to slowly waddle the scooter backwards, then turn into my lane. The entire flow of traffic came to a stop behind me while I waddle-turned then stutter-stepped to get going. I came home that night and immediately bought traveler’s insurance.


By the way, I rented that scooter from the nicest lady ever. When I told her that I was new to Thailand and needed to find an apartment, she offered to drive me to a place where an American friend of hers was staying. I didn’t end up staying there, but it was still generous of her.

In general, the Thai people were remarkably warm and welcoming. They smile when they meet a stranger on the street. They don’t mind much where you come from or if you’re a little different, as long as you’re nice.

It felt a lot like the culture in Los Angeles. Maybe it’s something to do with getting so much sun.

Back to my first day, I drove that damn scooter around all day and stopped by every place to ask for their monthly price.

I eventually decided I was doing it wrong. I needed a strong internet connection, so I went to Sinet–an internet service provider. I wrote down the name of every apartment they service, called every one of them, then rented a room with the cheapest one.

My monthly rent was around $135 USD, maybe around $200 after utility bills. It was significantly larger and more comfortable than the room I was renting for $600 in Los Angeles three years ago, which is going for $1,000 today.

I didn’t go in with much of a plan. While teaching in Korea, I was also writing freelance during my free time. As I came to the end of my one year contract, I was planning to move in with a buddy in Arkansas because the cost of living was so low. I found a website that compares cost of living around the world and worked out that I could support myself for a little while until I found a real job.

I got curious about what the cost of living in other parts of the world was like. I spent some time scrolling around their world map, and it turns out a dollar goes a hell of a lot further in Chiang Mai, Thailand.

As I researched it more, I found there was a whole sub-culture in Chiang Mai of people doing this. They’re called “Digital Nomads.” There are writers, programmers, online teachers, and anyone else who can make a buck online. They don’t technically need a working visa as long as they don’t take jobs from Thai companies.

I quickly found a writers group that meets every week. They ranged from rookies like me to travel writers to authors with several published books. A few of them believe that this digital nomad thing is the first step in a movement that will use the internet to revolutionize our relationship to work. A few of them were dreamers.

I spent far too much time alone, even for an extreme introvert like me. This is what my average day looked like:

11am: Wake up. Make a sandwich or get an omelette from the restaurant downstairs ($1). Eat while watching a TV show. Shows watched: Archer, South Park, Peaky Blinders, Narcos.

12-3pm: This was evening in California, so I’d often play computer games with friends from back home. Or if they weren’t on, I would still usually just dick around during this time.

3pm-6pm: Try to get some writing done.

6pm: Dinner. Usually street food. Noodles and chicken. Noodles and beef. Noodles and eggs. Rice and beef and eggs. ($1.25)


6:30pm-10pm: Teach online. Halfway through my time in Chiang Mai, I started using a Chinese app called “Palfish” to teach online. You click “go online,” then wait for a student to find and call you. You set your own rate and the student pays per minute. Sometimes you get a student immediately, sometimes you wait for hours. Usually I would play a game or practice bass guitar while waiting.

10pm-12pm: Panic and try to catch up on the writing and gig hunting I should have been doing earlier in the day.

12pm-2am: Open a beer ($1.40). Watch a show or play a game or read a book. Call it a night.

I tried to go to meetup groups about once a week so I wouldn’t get completely lost in the digital world and become awkward. Or more awkward than usual, at least.

I had been in a strange, long distance almost relationship with a girl from Macau. We met in California, then visited each other a couple times while I was in Korea.

She said she’d be able to visit often when I got to Thailand because tickets were cheap. I told her that’s great. I told her that I was tired of being on the dating market and I wanted something serious. I told her I wanted that with her.

By the time I left Korea, she still hadn’t told me when she would be able to visit. I told her not to worry about the price, I could pay for her ticket, just come visit anytime even if it’s only for a weekend. But after a month and a half without her starting to make a plan and hardly talking to me, I realized it wasn’t going to happen.

I eventually started dating a Thai girl. She was from a different Thai city, so we were both new to Chiang Mai. We knew I wouldn’t be staying in Chiang Mai for long, so we tried to keep it casual. But you can’t help it when you spend a few months with someone.  It sucked saying goodbye to her.

The dating culture in Korea felt alien to me. No feeling was ever directly stated, even something as simple as feeling tired or not. Every little action felt like a power struggle. But dating in Thailand, again, felt just like California. It was natural. To me, at least.

My writing productivity tanked about half way through. I had been doing copywriting, which is usually writing stuff like advertisements and sales pages. I thought I would enjoy this because I thought I would enjoy any type of writing. I realized something was wrong when I found myself looking forward to my teaching time more than my writing time.

After talking to other copywriters, I got the feeling that copywriting is a different language of writing from the writing I enjoy. It helped me realize what I love isn’t just writing, but storytelling.

I cringe to say this because it feels like a cheesy stereotype, but I think I discovered myself in Thailand. Except it wasn’t because of a minimal education in Buddhist philosophy or due to some drug fueled weekend on the beach. It was because I forced myself every day to do what I thought I wanted to do until I realized it wasn’t actually something I wanted to do.

As soon as I changed my focus to journalism, everything started making sense again. The people in the field were people I wanted to associate with. The writing was the kind of writing I wanted to do. I started to enjoy my work again.

That more or less takes us up to where I am today. I’m back in the US, applying to jobs at newspapers across the country. And until I get that job, I’m staying with my friend in Arkansas, watching college football and drinking craft beer and trying to hang on to the fleeting details of five months in Thailand.