Thai Ladyboy dating is hugely popular with a big proportion of the western foreigners visiting the land of smiles, but relatively few guys ever get past the transsexual street hookers that they meet in the red-light areas of the big tourist areas.
Bangkok and Pattaya are the main destinations for ladyboy prostitutes, but I won’t be providing much advice on this page about that. If you do want some info on the Thai ladyboy prostitution scene, have a look at my article:
Transsexual ladies in general are far more visible in all parts of the country than in other parts of the world, and that makes it a paradise for guys who are curious about them.
You won’t have any difficulty finding ladyboys in tourist areas, but as with bar girls these people are usually not trustworthy enough to get seriously involved with. On the other hand, if you head out to less well-traveled places, you probably won’t come into contact with many Thai ladyboys.
As per my usual recommendation, the best solution is to conduct your search online. My recommended dating site has a separate section devoted to ladyboy dating and you’ll find people there that you can have short term fun with, or something more serious.
Using a good ladyboy dating site also gives you the benefit of some extra discretion (assuming that you want to keep your private life away from prying eyes… and mobile phone camera/video technology).
Always keep in mind that your endeavors in the naughty bars can end up on Facebook or YouTube without your prior consent or even your knowledge, so the online route to finding adventure is usually a better choice!
I should point out that the advice I’ve given here has come from a wide number of sources, but those sources do not include my own personal experiences.
Thai ladyboy dating does not suit my personal preferences and I must confess that my romantic interests are strictly limited to women only.
I do not believe that this has affected the quality or reliability of any of the advice that I’ve given here, because it has been gathered from:
I hope and believe that it will be of some use to you.
This is a simple question that still, on occasion, causes some debate. The disagreement sometimes gets quite heated over whether or not a person’s gender is determined in purely biological terms.
As far as biology is concerned, a ladyboy has both x and y chromosomes and is therefore male. Others argue that gender is not restricted to biology and that it is a cornerstone of a person’s identity, which is determined by personality.
In simple terms, a ladyboy is a person who is born with a male anatomy but with a female persona. You can decide for yourself whether that makes them male or female, but in Thailand they are simply regarded as belonging to a third sex.
There are even some provisions made for children that identify with belonging to the third sex; some schools provide separate changing rooms and so on.
If you are reading this in the USA, the term ‘ladyboy’ is used in Thailand rather than the term ‘shemale’ that you might be used to.
It means more or less the same thing but with one important difference – the term shemale is considered offensive by many transsexual girls because it is linked somewhat to the porn industry, and it’s not a link that is appreciated.
It is best not to use potentially offensive terms if you want to get up close and personal with a ladyboy… unless you want to get up close and personally beaten up by a dozen of them!
The term ‘Katoey’ is also common, and acceptable, in Thailand so long as you get the pronunciation right (Thailand’s tonal language is not easy for beginners). At one time I had thought that a katoey was a ‘pre-operation’ ladyboy but no, it means the same thing and can be used interchangeably with ‘ladyboy’.
There’s also the term ‘phuying’ that you can use but, to be honest, I’m beginning to bore myself… If you stick with the term ‘ladyboys’ you’ll be fine. If you want to read up on these terms, then the Wikipedia link above is worth a look.
Thai ladyboys are transsexuals, i.e. men that identify with being female, they tend not to be sexually interested in other ladyboys. They don’t see themselves as being gay men and they are not interested in having sexual relations with gay men, they are interested in regular heterosexual men.
Since I’m on the topic, they are also not to be confused with transvestites i.e. people who like dressing up as the opposite sex but who do not identify with belonging to that sex.
As far as your own sexuality is concerned, the standard paradigm in Thailand is that being sexually interested in ladyboys does not mean that you are gay; there are lots of heterosexual men in Thailand that have had relations with ladyboys but who wouldn’t want anything to do with a gay man.
The terms pre-op and post op refer to whether or not a Ladyboy has undergone full gender reassignment surgery i.e. a vaginoplasty. If you hadn’t already guessed, this surgical procedure entails removal of the mail genitals and construction of genitalia resembling that of a female.
Most of the ladyboys in Thailand are pre-op; this is not always because they prefer not to have the surgery (or can’t afford the estimated 400,000 baht price tag), but rather because most of the men who are interested in ladyboy dating prefer them to be pre-op.
The preference of the Ladyboys themselves will usually be to resemble a female as far as possible, but they have to balance that desire against the possible negative effects of a bad surgical procedure (resulting in loss of sensation), as well as the expense and the loss of some interest from potential boyfriends.
Surgical operations that are much more common than the vaginoplasty are breast and hip implants. These are operations that are universally desirable and almost all Thai ladyboys will have had these operations done.
Aside from surgery, virtually all ladyboys will be taking hormone replacement therapy and they will, in many cases, have been doing so from an early age.
There is one unique factor to consider, regarding ladyboys, that makes Western men particularly attractive to them; it relates to a problem that is a serious concern for any Thai man who is dating a ladyboy i.e. the wishes of his parents…
Even if his parents are accepting of his preferences they will probably still pile on the pressure for him to eventually marry a biological woman in order that grandchildren can result.
The issue of children takes on an extra importance in Thailand compared to the west and it shouldn’t be underestimated. Children are the main care providers once they reach adulthood and many parents rely on that care.
Ladyboys cannot give birth to children and so there will be nobody to take care of them in their old age, that’s a big concern in a poor country with virtually no welfare state to fall back on, and where most people don’t earn enough money to save for retirement.
The inability to have children makes it rare for a Thai man to stay with a ladyboy on a permanent basis and, for the ladyboy, the lack of a permanent man in her life means no long-term support from a husband either.
Whilst in many Western countries child-adoption might be a possible solution to the problem of starting a family, it is a very uncommon in Thailand.
When it comes to financial problems, Thai ladyboys have got a lot of extra baggage and I’ve no doubt that this accounts for a large part of the over-representation of ladyboys working in red-light areas.
To give an idea of the extra strains they face (as well as the whole children/parental problem) here are a few of the issues they have to deal with:
Given the first two points, it’s almost certain that a significant proportion of ladyboys have given up any hope whatsoever of settling down with a permanent Thai boyfriend, and many of them have turned their attention to the possibility of a serious relationship with a Western expat instead.
The money that a rich westerner might bring is an added incentive of course.
You need to way things up fairly against the possibility that a ladyboy you are dating might purely be interested in you for money alone. When making that judgement you should also understand that genuine, successful, long-term romantic relationships in Thailand are often formed for practical (as well as emotional) reasons, and that this is perfectly acceptable in Thai culture.
Obviously, as westerners, our culture would have us feel quite disgusted to consider a romantic relationship for these sorts of practical reasons.
These cultural challenges are usually to blame when relationships turn sour, so my advice is to get accustomed to Thai dating customs before you get seriously involved in a romantic relationship.
On the specific issue of ladyboys working in red-light areas, I could argue that since their extra financial hardship is real, there is a greater likelihood that they are more or less forced to work there and would relish the chance to quit the bar scene if the opportunity came along.
Unfortunately, this misses the point.
The problem is that regardless of why a person is working in the naughty nightlife industry, once the lifestyle takes hold it becomes very difficult to break away from. This is as true for ladyboys as it is for Thai girls and you really should not get into anything serious with someone that has worked in this industry.
Don’t go thinking that you can ‘save’ someone from this because, as unfortunate as it is, the track record in this area speaks for itself... only a tiny minority of such relationships survive!
For some entertaining true stories about ladyboy dating, written by a selection of my readers, have a look at the stories below:
There are lots of Thai Ladyboy dating sites to choose from these days but my advice is to be very selective in decided which one to sign up with.
For the most part the specific sites that target Ladyboy dating alone look to me to resemble adult sites more than anything else. Another issue that might be of concern is that they are often quite small in comparison to the major dating sites in Thailand; the implication being that there are fewer people available to meet up with.
Trust is an important factor to consider with the online sites. The major sites are all highly professional and I have no concerns whatsoever in recommending them for ladyboy dating, but I’m less convinced by the trustworthiness of the smaller, explicit sites.
I’m not saying that they are scams, and I’ve no evidence that they are anything other than completely safe, but my instinct tells me to avoid recommending them as they do not have the rock-solid professional reputation that the bigger sites have.
I have been hearing about new Ladyboy dating sites that are in the planning stages. These are intended to be sites that are going after mainstream regular dating rather than the short-term liaisons that the explicit ladyboy sites are catering for, but at present I’m unaware of any that have an established reputation or a sizable client base.
Since I’m unable to recommend a targeted Thai ladyboy dating site, I’m only left with one option i.e. recommending one of the big players in the market. This is not a difficult task because there is only one major dating site in Thailand that has a facility for men seeking ladyboys.
I can give you my assurance that my recommended ladyboy dating site is top-notch and that it has an established client base of ladyboys.
Thai Ladyboy dating is known to be extra risky in terms of finding someone who you can put your trust in, and there are lots of people online that are looking for wealthy benefactors.
All of the advice and guidance that I have written in my Thai Dating Mega-Book is applicable to you and it might be worth considering purchasing a copy before starting your search for a suitable love-interest.
I’ve selected the profiles below as typical examples of the sort of ladyboys that you’ll find online, and then added some of my thoughts about them. Hopefully it will help you to organize your own thoughts about how to approach someone online.
The first profile looks like it belongs to a respectable sort of person. The first thing that is stated is that she is a nice girl and is looking for a long-term relationship. She goes on to state that she is not a bar-girl, but more importantly from my point of view is that the pictures provided present a respectable image.
Checking the details in any picture is extremely important and knowing what to look for is vital.
Sometimes you will see a photo and focus solely on the person whilst completely overlooking the setting. I’ve seen countless profiles that have photographs taken at a bar, and sometimes a bar with a foreign customer playing pool in the background.
That sort of thing is a very bad sign about the nature of the work being done by the ladyboy in question and I think that I needn’t say any more about that.
Another thing to look out for in photos is the style of clothing that the ladyboy is wearing. You should never forget that Thailand is a conservative country at heart and that modest clothing is preferred by any respectable person.
You won’t see much modest clothing in the tourist bars, and you shouldn’t confuse what goes on there as being in any way representative of what goes on in the real Thailand.
All in all I’d say that this profile is just the sort of profile that a man looking for a serious relationship with a Thai ladyboy should be looking for. There are no guarantees in life, but avoiding any obvious red-flags such as revealing clothing, heavy make-up, photos taken in a bar/nightlife setting and so on, will go some way to avoiding heartache should you end up getting emotionally attached.
At 22, this young ladyboy must have been using hormone replacement therapy for a number of years now. If you didn’t already know that this is not a female, then I think you might struggle to see that she is a ladyboy.
For those readers that are a little more familiar with Thailand, I think you’ll agree that the second picture does have a certain ladyboy look to it, but I think that that might be more due to the clothing than the aesthetics.
The typical young Thai ladyboy often wants to look sexy and will very often wear clothes to accentuate curves.
This ladyboy chose her surgeon well.
Her profile states that she lives in Pattaya and that she works as a model and earns a high income. I don’t know, but I would hazard a guess that she could be working at Tiffanys in Pattaya. The ladyboys there make good money from tourists by posing for pictures after a cabaret show.
She is interested in meeting men aged at least 18; she has not provided any upper age limit. She is a mere 162cm tall and weighs in at just 45kg which makes her a lot smaller than usual.
Unusually, her profile states that she is a Roman Catholic - the vast majority of Thais are Buddhists. She does have a certain Western look to her, with unusually fair skin, and I wonder if she has one parent of Western origin.
If this ladyboy looks like the kind of person you would like to meet, her profile states that she is interested in ‘serious offers only’; I’m not entirely sure what she means by that though.
I’ve come across a few profiles where the ladyboy in question is clearly frustrated at the guys who are contacting her.
I must admit that I’ve had a little chuckle here and there at those frustrations, but they aren’t really a laughing matter. It turns out that there is a large proportion of men contacting ladyboys online thinking that it is okay to use adult language, describing explicit fantasies… and some even expose themselves on Skype.
I can’t stress enough that this sort of behavior is highly unlikely to endear you to a ladyboy. You really should treat them in the same way that you would treat a respectable woman. If you do that, you will give your success chances a huge boost!
The photo here is of a 22 year old ladyboy from Bangkok. She is looking for a man of any age group, she is quite tall at 173cm and weighs in at a slender 54kg. She is university educated and she specifically states that she likes a man that is polite (so none of the sex talk!).
She also has a keen interest in foreign languages, European languages specifically; she can speak both English and French and is interested in learning Spanish.
Looking at this profile, I can’t find any red-flag warning signs to be concerned about. The photo look fairly respectable, her clothes are not too revealing and she wears only light make-up.
One good thing about this profile is the location; as mentioned already, she is based in Bangkok. I’ve mentioned elsewhere on my site that Bangkok is the best place to arrange meetings for your dating adventures if you want to meet someone serious (Pattaya is only good for short-term liaisons).
In Bangkok you are in the thick of it. Imagine if you traveled up-country to meet someone and things didn’t work out; you would be in the middle of nowhere with very few English speakers around to help you.
By sticking to dating in the main urban center you can easily arrange to meet lots of other people without having to trek all around the country in search of your ideal partner. If you were to restrict your search to Bangkok, you will still find lots of ladyboys that will be happy to meet up with you.
I think that of all the Thai ladyboy photos that I’ve featured here, this one is the most lady-like. I personally cannot detect anything from these pictures to suggest that she is not female.
If this profile was placed in the girls’ category of my recommended ladyboy dating site, I doubt that anyone would suspect a thing. Even her height gives no signal; at 165cm tall she stands at a very typical height for a female.
I think the point that I’m trying to make is that whilst you will be able to spot a ladyboy on 99% of occasions, there is always that 1% of remaining occasions where you will be completely in the dark!
My advice for men that are fearful of this is to relax; you can easily guard against any mishaps by casually mentioning in a conversation that you are not interested in ladyboys and would be upset to find that someone you thought was a girl is actually a ladyboy.
Don’t do this in a direct manner though.
The way to do things in Thailand is to skirt around an issue – maybe tell it as a story about a friend who was once duped by a ladyboy. As a final guard against any identity mistakes, you can always check your lady’s I.D. card when you meet her.
It will state her gender and her date of birth but both will be in Thai (the Thai calendar is not the Gregorian calendar that we use in the West, so you’ll need to do a little research).
This ladyboy is 29 years old, she’s interested in dating a man aged 18 to 50, and she lives in Pattaya. She states that she is a shy lady and that you should contact her when you come to Pattaya. There’s no information about her education level, her job or her income, and there is nothing in the photo to suggest anything about what she does for a living.
The final profile is of a lady from Chiang Rai in North Thailand. She is 27 years old and is interested in dating men from any age group.
She is 168cm tall and weighs 53kg. She is high school educated and she has stated that her income is 7,000 to 15,000 (baht per month), but she does not state what her job is.
With such a big income range I’m guessing that there is a large commission element, a little like the commission a bar girl gets from lady drinks (I’m not implying that she is a bar girl though, there are many commission based jobs in Thailand).
On her profile is an interesting message regarding true love; it states that true love is a little like a ghost in that everyone talks about it but only a few have seen it!
I think that I should mention something about superstition in Thailand. Basically, most Thai people are very superstitious and believe quite firmly in the presence of ghosts. This is nothing to do with Buddhism, and I’m not sure where it stems from but it is taken quite seriously.
I know a number of Thai girls who are scared of bad spirits (called ‘phi’ and pronounced ‘pee’). If you have ever been to Thailand and noticed the miniature houses that sit in the gardens/grounds of buildings, you may have wondered what they are. They are spirit houses.
When dating a Thai, you are well advised to take the whole ghosts/superstitions thing seriously because they can get quite concerned about such things.
Getting back to this dating profile, I think that it is worth mentioning one more thing i.e. the city in which the lady lives. Chiang Rai is, by all accounts, a very beautiful place and well worth a visit if you want to see the hill tribes in the north of Thailand, and/or you want to go on a proper elephant trek.
There are many reasons to visit Chiang Rai, but I don’t recommend it as a ladyboy dating venue.
It is only a small city on the northernmost tip of Thailand and it is a 90 minute flight from Bangkok. If you were to travel there to meet someone and things didn’t work out, you’d have wasted a lot of time and money.
I seriously doubt that you will find a more tolerant society than that of Thailand, and the laid back attitude that the local people have towards transgender issues is ultra-relaxed compared to some countries in the world.
Compared to some countries where the unnamed ‘religion of peace’ is dominant, the prevailing attitude is that homosexual people should be thrown in prison (or off the nearest tall building), so I think you’ll agree that there is a sizable contrast in the way that non-heterosexual types are treated around the world.
In particular for you, as a tourist in Thailand, you can relax in the knowledge that any ladyboy dating adventures that you have will raise absolutely zero interest from other people.
Nobody will care in the slightest.
That’s not to say that there is no discrimination in Thailand against transsexual people, they are regarded has having a mental disorder, and that does restrict a lot of employment opportunities.
Lack of understanding or acceptance is probably always going to be a problem for ladyboys and, although I am not interested in them sexually, I do have a great deal of respect and commiseration for them when they are being called abnormal and deranged.
Just consider for a moment what they have had to deal with throughout their lives. From an early age they have faced ridicule, many have been beaten up, they are sometimes disowned by their friends and family, as adults they are barred from working in many jobs.
Throughout it all, they have pressed on and stood up for themselves. Whatever your sexual preference, you have to admire that kind of strength!
Some people take issue with ladyboys seeing themselves as being female and will go to great lengths to demonstrate that they are not technically female. I think the issue is irrelevant; ladyboys believe that they think and feel as ladies do and they just want to be treated as such. I think the issue is an emotional one, not a technical one.
Some of these guys can get quite heated about it and you have to wonder why that is. My money is on prejudice based on lack of understanding, fear of the unknown, or religious conviction. Alternatively, it could be due to some frustration over repressed sexual attraction…
The answer to this question is not immediately obvious and you could ask a million other questions about how a certain country has developed a certain attitude towards a given thing without getting any conclusive answers.
There are certainly some things that help generate the tolerance level, Buddhism in general is a remarkably tolerant religion and since it’s the overwhelmingly dominant religion in Thailand it does help matters. It can’t just be down to this though, otherwise every Buddhist country would share similar attitudes.
I think that the unique aspect about Thailand is the general concept of avoiding conflict where possible. Of course it also helps that sex in general is not seen as being quite the taboo subject that it is in other regions of the world. Freedom to express oneself in whichever way is preferred is seen as being perfectly natural.
You should note that even Thailand does not have complete equality, Time magazine has featured an article that describes a far from perfect picture (click here to read it), but there’s no question in my mind that the tolerance level here is extremely high compared to any other country I’m aware of.
There are lots of ladyboys in all parts of Thailand but, in terms of meeting them, there is a difference compared to meeting ladies. If you are looking for romance with a lady then there is every chance that you might intend to take that lady back to your home country at some point where you can continue the relationship.
When it comes to transgender options, most men come to Thailand precisely because they are too shy, or too afraid, to have these sorts of relationships back home. That makes holiday romances much more likely than long-term relationships, and so there is a much higher concentration of ladyboys in tourist areas like Pattaya than in other areas of the kingdom.
Meeting girls as they are walking down the street, or working in a shop etc., is the best way to find someone special. But, since you won’t so easily spot a ladyboy walking down the street or working in a shop, you really need to consider online dating as your best option.
This is a very popular question that gets bandied about the Thai online forums very frequently. I don’t think anyone is qualified to give a definitive answer to it but plenty have tried.
There are those people, Thai people in particular, who feel that attraction towards a ladyboy does not mean that you are gay. They argue that ladyboys are feminine in appearance and character and that to be attracted to that is not homosexual.
Others argue more on biological grounds that a ladyboys is genetically a man and that any man who is attracted to a ladyboy must be homosexual. Personally I think that the whole question is mute and meaningless. The people who get embroiled in these debates usually have an axe to grind and just want to vent some anger for one reason or another.
My opinion, for what is worth, is that attraction to a ladyboy is something different. I don’t think it either heterosexual or homosexual, it belongs to a different sort of sexuality altogether.
What I will say is that it appears to be much more common for men who are currently involved with a ladyboy to only have had previous relationships with women. I think it is much rarer for a man whose previous relationships have been gay relationships to develop an interest in ladyboys.
No, you should be aware that ladyboys see themselves as being female and that they regard other ladyboys as being female – at least in terms of their persona. That means that they are not usually attracted to each other. The want to be with heterosexual masculine men the same that a heterosexual woman would.
Believe it or not, there would be a greater danger of this sort of thing happening if you were involved with a bar-girl rather than ladyboy dating. It is well documented that many bar-girls are either homosexual or bisexual.
This lovely petite young lady, 28 years old and only 47kg, is looking for a western man to be her boyfriend. If you would like to meet up with girls just as lovely, you can with
My Recommended Dating Site: