The challenges of dating ladyboys online


Unless you’re living in Thailand / Philippines (and some other South East Asia countries), chances are that the population of transgenders (ladyboys) in your place is pretty low. Therefore, the Internet placed itself as the best way to meet one of these special girls. And even though you’re living in South East Asia, online dating is also a powerful tool, because your dream girl is not likely to be at the corner of your street right there waiting for you!

Online dating has become so popular, and it raises its lot of issues and challenges. In addition to that, online dating for transgenders raises even more difficulties that are really inherent to the transgender world. I will try to write about what I believe are the biggest issues, in the most casual way possible 🙂 and how I plan to address them.

Ladyboys are mistaken for sex objects

Ladyboys are objects of fantasy, that’s a fact, and all men feel at first a sexual attraction for them, probably before considering a relationship. It’s kind of confusing to them, but probably it’s the same curiosity that a teenager feels when he’s first confronted to porn, he feels curious, he feels aroused and that can fills his mind all day and night (or I was the only teenager obsessed by sex? I DON’T THINK SO), but it’s different from the feelings he will then have for the other girls. Porn is porn. Feelings are feelings.

Sadly, the Internet is filled with shemales, dick girls and ladyboy porn (as they call it) and there are only a few sites and services dedicated to them that are not related to porn. Not a single dating website which is of quality (there are a couple of amateur sites not so well designed) or decent (most will associate transgender dating with sex encounters).

That leads to confusion and misinformation for men, who will often associate transgenders to sex objects or sex workers. By the way it’s something I’m trying to change with my blog and my educational book (it’s almost the first anniversary hey).

I personally want to address this issue by providing a quality service for transgenders and men who want to meet and find love. I started to develop a dating website that I plan to make a reference in online dating for ladyboys, as this will be of the same standing as PlentyOfFish or Match (big general dating sites). It will be called, you can subscribe to the early updates as soon as now, on the official website My Ladyboy Date or on the Facebook page.

At no time on my dating website will it be suggested that this is more pornish than any other general dating website. Unlike the competitors, I will not play that game. I don’t want it to look cheap either, being a web designer myself, I will put all of my efforts to do something of quality, like any service is expected to be in 2012 (2013 soon!) and educational content will be offered FOR FREE to any man subscribing to the service.

Ladyboys are mistaken for sex workers

Asian ladyboys suffer from a bad reputation of being either sex workers, or having their motivation driven by money. This is of course a false statement. When there’s smoke there’s fire, yes, but no one shall generalise. Amongst the population of transgenders, sex workers are the most visible, and that’s perfectly normal and inherent to their job, they need to get attention so that they attract customers. Most of the transgenders, transgenders with decent occupations, are not looking for attention, they’re happier living a normal and discrete life.

Online dating is a target for sex workers and other gold diggers of course. What a best place for them to find a generous and naive man, being cute and lovely, getting liked, and finally ask for some money or offer a cam show?

My dating service will have a strict policy towards these members. It’s perfectly okay for a sex worker to join the site (it’s open to everybody and everybody deserves to be happy and find a partner, whatever their occupation), as long as she’s not using it only for the purpose of meeting men in view of a relationship. Advanced algorithms and scripts will be put in place to spot these behaviours and there will be no tolerance. I’m not afraid of seeing my number of members dropping, as I believe decent transgenders are enough to populate the website. This is for dating and forming relationships. Not for cam shows nor escort services.

There are no-life wankers who like to maintain fake profiles

That’s pretty general in online dating, but true, some people have nothing better to do than to maintain fake profiles online. Well, why not, if it’s fun for them… but they will not last long on Scripts and manual verifications will be in use to prevent such profiles (photo verification for example). Moreover, to build trust amongst the members, I will put in place many verification procedures (such as email and phone number verification, or linking the profile to a Facebook, Twitter or LinkedIn account…)

An important part of online scammers come from Asia

Scamming is very rampant in online dating, and it’s especially coming from third-world countries in Asia and Africa. Since Thailand and Philippines are known to have the biggest population of ladyboys in the world (and they’re third-world countries!) scammers are then an issue when you’re looking for a ladyboy girlfriend.

Unfortunately for scammers, patterns can be easily spot out by a series of scripts and manual verifications that I will set up. It’s not an easy task and I understand that current websites (which are mostly not professionally managed) have a hard time dealing with these issues, it requires cognitive science analyses, and pretty complex algorithms (if not reading every message and profile manually? duh!). Members of MyLadyboyDate shall not be worried about scammers and shall be dating serenely, scammers detection is one of the main issues I want to address. Of course it’s never possible to ensure that the person you’re talking to is genuine, it’s human nature, but I want to lower the risk as much as possible.

Liars and perverts put the serious guys in obscurity

Let’s talk about men this time. It’s not just for ladyboys, but ever since there are males and females on earth, some men always lie to women just because they want to get laid. These are the guys who feel insecure or are not experienced in picking up girls, and they believe the only way to get laid for them is to pretend they’re looking for something serious. And that is very present too in the transgender scene (oh my god, I ban several idiots like this from my Facebook group every day!)

These insecure guys usually don’t show a real picture of themselves, and they’re cheap. Ladyboys are not naive, they’ve seen it all, believe me lol (or maybe you can fool a very young and inexperienced ladyboy, but she will not be fooled twice). Even though it’s impossible to know the real motivation behind every human, my dating website will be designed with this focus. Members who don’t post a photo will have restricted access (yes these guys are usually the ones who don’t post a photo). Coupled with my automated scripts preventing fake profiles, that will lower the number of guys like this, or at least raise a warning on their profiles.

Eventually, memberships for men will cost a monthly fee (only for men, don’t worry, it will always be free for ladyboys). Why not making a free dating website? Simple, because there is too much rubbish on free dating websites! This kind of guys are cheap, even if living in first world countries, they like better to waste their time lying to girls for getting the girl naked on webcam for free, rather than spending a few dollars in a dedicated sex cam site. A man who is willing to pay 30 dollars for accessing a dating website already proves himself more worthy and serious. With the profit margin, I will be able to hire staff (exclusively ladyboy staff of course) who will ensure the quality of the members by regularly checking profiles and behaviours.

A new dating website, tailored for you

These are basically the main challenges I see about online dating for transgenders. All of them are related to trust, which is a human trait and might look difficult to address with computing and algorithms… But I’ll accept the challenge for you 🙂 Because it’s only a niche (a small part of the market), dating websites haven’t put the biggest effort in working this out. I believe transgenders are not a niche anymore. I believe transgenders have reached the point in which they deserve decent services and decent websites, just like the general public does. And I believe I shall be working on this for them. For you.

The development of my dating website is going pretty well so far 🙂 A private beta version shall be ready before the end of 2012 (invitations will be sent to my friends and the members of my Facebook group) and I expect the public beta to be open in January or February hopefully. The site will be free for all until the official launching (probably in a couple of months after the public beta period starts, when the site will be mature enough and address all the issues above well enough). You can follow the development on the Facebook page, on Twitter and also subscribe to the early updates on the temporary homepage.

What do you think about this? What are the challenges you see in online dating for transgenders / ladyboys? What would you like to see in a dedicated dating website like that?

French young man living in the Philippines with my ladyboy girlfriend. I wrote a book about my experience on dating trans women here and I created the first decent dating site for trans women there

You liked it? You can share this article to your friends!

Receice my posts by email, right to your inbox

Get great content about love relationships between men and ladyboys, techniques, tips and even personal ads from quality ladyboys looking for love.

15 thoughts on “The challenges of dating ladyboys online

  1. Interesting article. Finding a ladyboy who is not working in the sex industry makes it easier to enjoy a long term relationship.

    Could you tell me how much money is needed to live in The Philippines with your ladyboy girlfriend? I guess, it depends on where you live, Manila being more expensive than smaller cities. If you could give me some numbers for Manila, Cebu and smaller cities I would appreciate because I am planning on moving to The Philippines. I like living in a clean place with A/C and fast Internet connection.

    How are the people treating you when you go out with your ladyboy girlfriend? Can you enjoy being with you ladyboy alone or are there many people being nasty about it? It is certainly easier to live with a ladyboy in a big city such as Manila but what about smaller cities? Would it be possible to live with a ladyboy girlfriend in smaller cities such as Bacolod, Dumaguete or Cagayan de Oro?



    • Hi Greg and thank you for your comment.

      To give you a number, we live here in Manila with more or less 1 000 euros a month. We live in Makati which is the central business district of Manila. It’s very decent for a westerner, although there is more posh and more expensive. It’s clean, safe, all facilities are around.

      As for the Internet, I recommend you don’t put big expectations, it’s shit everywhere in the Philippines (if you’re used to broadband in Europe or US, you will feel a BIG DIFFERENCE). It’s usable, but you won’t be able to download movies like you do in Europe…

      I have absolutely no problem getting around with my girlfriend (well, she is very passable and nobody can find out she is not a real girl, so it makes things easier of course). But even when we hang out with other ladyboy friends, we never have issues. Filipinos are very accepting towards ladyboys here, in society. You might encounter assholes, like everywhere, but a lot less than in France for example (I am French, I can tell).

  2. Thanks for the quick reply. Only 1000 Euros in Makati! And you are living with a ladyboy! I thought it was much more expensive especially in that area. You must be very good with money. And your girlfriend is also reasonable.Some think that we are all millionaires… I will probably be in The Philippines in 18 months. I can’t wait to be there and find a lovely ladyboy girlfriend to live with me.

    Merry Christmas,


    • I am not a millionaire, but 1 000 euros a month is big money in the Philippines. Besides, my girl got her first job recently and she’s bringing in 500 more euros, some of her revenues go to her family but she is also sharing expenses with me.

      Basically I’m living the same way I used to live in France (i.e I clean the house myself, cook and have dinner at home, I don’t spend too much on consumables…) Many people here have a maid and a cook, it has an extra cost. But I was brought up that way, I almost feel uncomfortable if somebody is cleaning the house for me lol.

      If we go out much or fly to the beach, our monthly budget goes up, but for “just living comfortably” in Makati, 1 000 euros are enough.

      I must point out that I’m lucky with my girl, she is working and sharing expenses, even though I’m clearly earning way enough to sustain our couple alone 🙂 Am glad we are living the European way.

  3. You are lucky to have a girlfriend who is working and can pay some expenses. But if she was not working and you had to pay for everything, how much would it cost you to live in The Philippines? Unemployment is high in The Philippines, so is the probability to find an unemployed girlfriend. It is hard enough to find a good ladyboy girlfriend, I would not want to reject one simply because she is not working.


    • 1 000 euros per month in all, more or less, whether Anne is sharing expenses or not (before she was still a student and didn’t bring anything)

      Well, I know plenty of girls here who have a job and are single, if you may want to join my Facebook group, you will meet many 🙂

    • Hi greg It’s me Lea 22 yrs old from Manila Philippines. Worked as a Customer Service Representative here in Manila. I heard that you are looking for a lovely ladyboy and I’m a bit interested of it, like getting to know each other..Don’t you? by the way you can write me on my email address and i will send you some of my pics.. Happy New Year..

  4. Hi To the Author,

    I really love all your articles, but one thing you missed you forgot to mentioned that men are more sensitive than women.

    I’m a ladyboy from philippines, you’re right that we innocent and decent and discrete people were affected because of what other ladyboys doing. They messed up in the soceity.

    Most men are just for play and flirt. I’ve been in a different dating sites for 5 years, but no one’s sincere..How sad, and still waiting for my Mr. Right.

    I hope I could find him, a true, sincere, serious and loving man for me. I want a long term relationship,..

    Wishing you all the best..


  5. oh God! Simon dear…I’ve been searching online for 8 years in finding the perfect guy 4 me and unfortunately i found perverts… is it really hard to find a good guy especially when am not the flirty,gold digger,materialistic kind of ladyboy?? not to mention my age.. am already 34, and surprisingly am single!

  6. Hi Simon,

    First of all let me say thank you and good job for working on your wonderful website. it has a lot of decency and honesty. and the way you understand the feeling and lifestyle of lady boys is really amazing. Well honestly, I envy your girlfriend for having such a nice boyfriend like you..


    Best regards,

  7. Hi Simon I am a young at heart 56 yr old guy living in Australia im looking for a relationship with a lady boy and I want to know are they looking for much younger guys than me am I too old

    • Age doesn’t matter. Actually I very often hear my friends (Filipino ladyboys) telling me they’re looking for older men, more mature, more likely to commit to a serious relationship with them.

      So no, I don’t think you’re too old 😉 Check out my dating site, there are tons of single transgenders looking for a relationship:

  8. Great article Simon – my Thai nephew who is a 36 year old post-op very beautiful and cultured Thai ladyboy met his Singaporean husband online and they have been an item for over 5 years now. They are both very happy the only problem is that his Singaporean Chinese partner is in fact we think gay and has yet to tell his conservative Chinese parents. Hmm we shall see. Many thanks for creating such a wonderful resource.


Leave a Reply

Your email address will not be published.