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Dating A Ladyboy: What Secrets You Must Know?

by John Santana

Ladyboys are incredibly beautiful, and this is just one of the reasons why more people are becoming a bit more open to the idea of dating a ladyboy. As the world is becoming a bit more open and accepting of LGBTQI relationships, if you have ever been interested in the idea of dating a ladyboy, there is no better time than now.

When you first start dating it can feel like a mixture of emotions, it is exciting and overwhelming at the same time. Well, this is how you might feel when you start dating ladyboys. Luckily, this article highlights what you need to know before dating a Ladyboy. Including, how you can meet a Thai Ladyboy and a few tips for dating a Ladyboy.

This article will help you navigate through your dating life and maybe even help you find your special person. Here is everything you need to know about dating ladyboys.

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About Thai Ladyboys

This might be surprising but Thai culture is quite expecting of the LGBTQI community. After all, Thailand has a deep history of transgender people, which dates back to the 14th century.

However, later on, the negative beliefs of Western society about transgender people started to spread which affected the LGBTQI community in Thailand. It was only until the mid-90s did the society in Thailand become more accepting of the LGBTQI community.

There is some confusion when it comes to Thai ladyboys, this is usually because of the name ‘ladyboy’. To help clear this up we are going to quickly break down what ladyboys are and the reason why they are called ladyboys in Thailand.

In Asia but mainly in Thailand, ladyboys are called Kathoey which loosely translates to ladyboy. This is where the term ladyboy has come from and seemed to stick in Thailand, especially around the tourist areas. While there are ladyboys in Thailand who do not mind being called a ladyboy. However, they do prefer being called Kathoey because this is exactly who they are and usually identify themselves as.

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Meaning of Kathoey

The term Kathoey is an umbrella to several different sexual identifications, which means what one identifies themselves as. The common sexual identification of all ladyboys (Kathoey) includes:

  • Trans women – Trans woman is someone who is biological a male and they have been identified as a male since birth. However, they do not identify as male and have chosen to transition from male to female. Meaning that they would be on hormones and later on have gender reassignment surgery to fully transition to a woman.
  • Effeminate gay men – An effeminate gay man is someone who is biological male however, they are more comfortable with adopting female behavior. This can include female style, mannerisms, and behaviors.
  • Intersex – An intersex person is an individual who is born with sexual anatomy that does not fall into the basic male or female categories. Which gives this individual the option to choose which gender they identify with better. As a ladyboy, this means that they would identify with a female.


If a person is androgynous this means that they were born with both male and female reproductive parts. However, a ladyboy who is androgynous will usually feel more comfortable identifying as a woman.

Note: all the sexual orientations above are considered to be a real ladyboy.

Personality of Ladyboys

While there are a few people who typically say that ladyboys usually have similar personality traits as each other. Some common traits that are usually included in this list consist of being romantic or being extremely feminine. Even though there definitely will be quite a few ladyboys who are feminine and romantic, this does not mean all ladyboys are.

After all, ladyboys are ordinary people who will have their unique personalities. With thins that things that they like and things that they dislike. Which is the same thing that you would expect if you dated a straight person.

This is something that you should be mindful of especially if you are planning to date a ladyboy. The last thing you want to do is start to date a ladyboy with false expectations and stereotypical beliefs. A date like that will not end well, so just all keep in mind that ladyboys will have their personalities just like everyone else.

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Serious or Casual Relationships with a Thai Ladyboy

Whether you are looking for a long-term relationship or you are simply looking for a causal fling with a ladyboy. Thai ladyboys are usually open to both options it will just depend on the person that you are interested in and what they are looking for.

Just like with any relationship before you start getting serious or after a few dates it is always a good idea to talk about what both partners want out of the relationship. It is a good idea to try to have this conversation sooner rather than later to avoid hurting anyone’s feelings and wasting their time.

It is also important to be completely honest about the type of relationship you are looking for. The last thing you want to do is lead someone on or be lead on by someone. This is why it is better to just be transparent, it will be better for both partners in the relationship.

Benefits of Dating a Ladyboy

There are many benefits of dating a ladyboy including the fact that you are opening yourself up to new experiences. No matter what you identify as when you are open to the idea of dating a ladyboy you will be in store for some new experiences. You could even possibly find someone that you want to be in a serious relationship with.

A benefit of having a ladyboy girlfriend that has to be mentioned is that the vast majority of ladyboys are beautiful. This includes being with or without makeup, generally, ladyboys are beautiful people.

Another benefit of dating a ladyboy is that usually, ladyboys are confident and do not get easily offended. Which does make it a bit easier to be someone confident in who they are and will not get easily offended if you say something that could be offensive by mistake. However, you should try your best to avoid saying anything offensive.

While it is true that not all ladyboys will be confident and won’t get offended too easily because this is influenced by their personalities and everyone is different. However, the vast majority of ladyboys are confident and don’t get offended easily usually because of what they have been exposed to.

Even though Thai culture is accepting of the LGBTQI community, there will still be people who are homophobic. This is why many ladyboys are used to experiencing situations like these and can make them stronger people in the long run.

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15 Things You Need To Do Before Dating a Ladyboy

Ladyboy dating is quite different and there are a few adjustments that you will have to make if you want the relationship to work. If you are serious about wanting to date a lady boy. There are a few things that you will need to be prepared for in this relationship including:

1. Treat Them as a Partner

While this should not need to be said, it is something that a lot of people who date ladyboys seem to need a reminder of. Quite a few people forget that the ladyboy that they are in a relationship with is supposed to be their partner. At times there is an imbalance of power on either side and this can lead to an unhealthy relationship.

2. Always Be Respectful

Respect is a part of the foundation of a relationship. A healthy relationship cannot exist if both partners do not have mutual respect for each other. However, some people date ladyboys. Simply because they are ladyboys which makes them viewed a bit different this leads to them not gaining as much respect in the relationship.

This should happen in any relationship. If you are not willing to always be respectful towards your partner then you should not be in that relationship. Especially if you are disrespecting someone because of how they identify.

3. Do Not Date if it is a Phase

A common problem in the ladyboy dating community is that quite a lot of people are fascinated by them. This could be because of their beauty or they don’t understand exactly what a ladyboy is. However, this curiosity can be harmful because it tends to make these types of people want to date a ladyboy simply for the experience of it.

Usually, you will see a foreign man trying to get the attention of a ladyboy, and most times it is just because they are curious. While it is fine to be curious but if you start dating a ladyboy just you are going through a phase or you just want to brag about it.

In this case, you should avoid dating ladyboys because you do not have the right intentions. It is important to keep in mind that they are people who have feelings.

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4. Avoid Using Offensive Terms

Even though it might seem obvious that you should completely avoid using any terms that will offend your partner. This is something that people need to make sure not to do especially when dating a ladyboy. Even the term ladyboy might seem offensive to certain ladyboys because they identify as Kathoey. This means that they are only comfortable with being called Kathoey.

This means that you should stop using the word ladyboy altogether. Whenever you speak about your partner and if you need to mention what they identify as. Make sure to use a term that they are comfortable with.

5. Establish Ground Rules

You don’t need to establish the ground rules of your relationship with a ladyboy on the first date. After all, you don’t even know yet if you will be seeing them again. On the first date just focus on getting to know them.

However, after you have had a few dates with someone that you are starting to develop a connection with. Then it would be a good idea to discuss setting some ground rules with them. Specifically about whether you want to have a serious relationship or you want to casually date them. You should also discuss what you are comfortable with doing in the relationship. As well as, if it is an exclusive relationship or not.

6. Avoid Stereotyping

When dating anyone you should never stereotype them, stereotyping can be hurtful and disrespectful. So when you are in a relationship with a ladyboy make sure that you do not apply any typical ladyboy stereotype to them.

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7. Do Not Ask Your Partner About What They Looked Like When They Were a Man

Even though you might be curious about what your partner looked like before they transitioned into a ladyboy. It is just respectful to avoid asking to see pictures of your partner. Certain ladyboys prefer not to remember what they used to look like because it may have been a difficult time for them.

Unless it is their idea and they want to show you then it is fine because this means that they are comfortable with it. However, when your partner does show you what they used to look like make sure your reaction is appropriate because it can be a sensitive topic. Your partner is also choosing to be vulnerable with you so make sure to be respectful of that.

8. Understand Your Sexual Identity

After dating a ladyboy for a while you might start developing feelings for them. Although, if this is your first LGBTQI relationship you might begin to wonder about your own sexual identity and what you would identify as because you are dating a ladyboy.

Well, you know your sexual identity and how you feel towards different genders. However, it is important to remember that straight men date ladyboys as well. After all, many ladyboys are trans women which means that these men are in a relationship with a woman.

9. Learn About Your Partner Sexual Identification

Even though your partner is a ladyboy you still need to be open with them and ask them about what they identify as. If you are confused about how they identify or why you should politely ask them just to gain some understanding of who they are.

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10. Support Your Partner’s Sexual Identity

It is also important that you support your partner’s sexual identity. If you are dating a ladyboy and you find whatever they identify as strange or it makes you feel uncomfortable. Unless you can learn to be supportive of their sexual identity and try to understand it. However, if you find that you are having trouble accepting their sexual identity then you should not be in a relationship with them.

11. Use the Correct Pronouns

Now that your partner has been open with you know exactly what they identify as. Out of respect, you should always use the proper pronouns that they prefer. It can be extremely hurtful and disrespectful to use incorrect pronouns after someone has confided to you what they identify as.

Although, you might find yourself making a few mistakes and first saying the wrong pronoun. As long as you correct yourself and your parents see that you are trying then they should be okay with the effort you are putting in. It will take a bit of time to get used to if you have not been using the same pronouns since the start of the relationship.

12. Talk About Sex Together Before Starting a Sexual Relationship

Once you and your partner are ready to have a sexual relationship it is very important to talk about sex together. Even though this should be something that is done in all relationships because it helps inform your partner about what you are comfortable with. Also, you will know what your partner’s boundaries are.

However, talking about sex when you are in a relationship with a ladyboy is very important. This will make the experience a bit more comfortable. If you feel you are not ready to talk about sex with your partner then you are also not ready to be in a sexual relationship with them.

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13. Be Mindful About Body Their Body Changes

Once you are closer with your partner and you know a bit more about their bodies then you should be understanding that their bodies will be a bit different. If you are dating a transgender women, then you need to do a bit of research.

So you can understand the effects the female hormones will have on your partner. As well as, how this can impact your partner. Female hormones cause mood swings and it has quite a few side effects. Just try to keep in mind what your partner’s body is going through.

14. Avoid Comparing Your Partner to Cis Women

If your partner chooses to define themselves as a woman then you should be respectful and accept that decision. You might be thinking that you have accepted it and that is exactly how you view your partner.

While that is a great thing, make sure that you never compare your partner to cis women. Not only will this be disrespectful to your partner but it also shows that you don’t view them as a woman. Which is something that can hurt your partner deeply.

15. Prepare Yourself for a Different Dating Experience

If this is your first relationship with a ladyboy then you should mentally prepare yourself for a different type of relationship. Even though all relationships are different, dating a ladyboy will be a completely new experience.

You will have to be a bit more open and talk to each other about any questions because you will have to learn new ways of doing things in your relationship. However, it is always important that the both of you communicate with each other because this is what will make this a healthy relationship.

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How To Meet A Thai Ladyboy

There are two different ways that you could meet a Thai ladyboy. It all depends on what you want to do and how serious you are about dating a ladyboy. This includes visiting places where ladyboys usually are and meeting them in person. On the other hand, you could meet ladyboys online.

Meeting in Person

If you are interested in meeting a ladyboy in person then your best bet is to visit a few spots in Thailand. A few cities that are filled with beautiful ladyboys include Phuket, Chiang Mai, Pattaya, and Bangkok.

What’s great about Thailand is that there are a few places you can go to like clubs or bars and you will be able to casually meet a ladyboy. After all, it is better to casually meet a few people and see who you connect with the best. Especially if you are interested in a long-term relationship.

Online Dating

If you are nervous about going out and approaching someone that you are interested in then you could always try online dating. There are many dating sites to choose from that are for specifically meet ladyboys online. This includes dating sites like TrulyLadyboy, My Ladyboy Date, and more. However, always be cautious when using a dating site.

There are many benefits of choosing online dating such as you will be able to get to know the person before your first date. Dating sites also allow you to view dating profiles and create your own. Which can help break the ice when you start speaking to someone new.

Final Thoughts

Now that you know what it is like dating a ladyboy you can decide if you are ready for this kind of relationship. If you are interested in ladyboys, then you should definitely go ahead and date a ladyboy. Even though dating a ladyboy comes with a few challenges and you will have to get used to a new type of relationship there are also great benefits.

It’s always good to be open to new experiences and dating different people because that person might just be someone you want to be in a long-term relationship with.

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John Santana

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