Almost certainly, many of the foreign men who are looking to date Transgender women from Thailand or The Philippines have dated before. They may have dated genetic women rather than Trans women and, therefore, think they know all there is to know about dating a Ladyboy. After all, a Trans woman is essentially female…, just with some subtle or not-so-subtle differences!

Another thing that many men who have dated before overlook is that times have changed. Especially for older men. Nowadays the most successful dating of Trans women is via online dating. Online dating using a specialized ladyboy dating site is so much easier than before, with instant connections, and so much more choices for women.

The slightly older generation may not have had this experience of dating online before. So, here are some great tips to help you make the most of your time and effort in finding the Trans lady of your dreams:

Your profile on a ladyboy dating site

It cannot be stressed enough how important a great profile is. Don’t just write down the first words which come to mind. Read, check, and re-read what you have written. If you have someone who is close to you and you can trust, ask them to read it for and maybe even suggest some improvements.

Don’t forget, your profile is the first thing a Ladyboy from Thailand or a Trans-pinay from The Philippines will read about you. You want to impress them and encourage them to read more. And, of course, reach out and contact you.

So, when you are reading through your profile ask yourself: Does that really sound like you? Are you presenting yourself in the best possible way? If you were reading it, do you think it’s appealing enough to make a Trans lady think you might be their perfect match?

But, perhaps, most of all be honest. If you are slightly overweight, don’t say you are well toned! If you are over 50 or 60 admit it. Don’t overexaggerate your good points; although, conversely, don’t accentuate your bad ones!

As far as possible make sure the budding relationship is real

It’s very easy to start “dating” the first Transgender women who shows interest in you. After all she must have liked what she read. Or saw your profile photos and felt they were good ones.

But take your time and select a few Ladyboys or Trans-pinay who appeal. Start conversations and ask your selected Trans women any reasonable questions. Certain things of a more personal nature should be “off-limits”, at least in the early days of a relationship. However, if you know enough about Trans women you should have a good idea what to ask and what to not without us telling you.

Also be prepared to answer any reasonable questions the Trans lady may ask, about your job, where you come from, why you like Ladyboys and so on. That’s only fair as a successful long-term relationship is going to be a two-way thing, right?

It’s best to gradually narrow down the number of Trans women you are talking to until you have maybe 2 or 3 who are you are getting on really well with.

Then it’s time to take the dialogue to a different stage.

Time to see if the budding relationship(s) is real. Only you will really know but there are certain things to look out for. For example, if the Trans lady is more interested in your financial status than you, try and work out if this is innocent questioning or she has an ulterior motive. Or if she is asking to come and live with you in your country when you have only known each other for a short time, think twice, maybe even slow down the speed of dating.

It’s fair to ask questions as to why she likes foreign men. What she does for a job/career. What are her ambitions and objective in life? How would she manage in an overseas country if you are/were working?

Different stages: no two ladyboys are alike

The final tip in this article is an important one.

Don’t forget that no two Transgender women are alike. So, don’t treat them all the same. You wouldn’t do that if you were dating other, genetic women!

Firstly, they may be from different countries such as Thailand (Ladyboys) to The Philippines (Trans-pinay) or even Vietnam. Therefore, they are culturally different from each other. Different languages and different outlook and views on life. Maybe even different educational standards.

But an in the extra dimension which relates to all Trans women no matter where they come from. They may well be at different stages of their journey to “complete” womanhood if, indeed, that is their goal. By this we mean that some Trans women may be on hormones but have had no surgeries. Some may have had breast implants (or grown their own breasts thanks to the hormones); some may not. And then there is the “big” op. Some Asian Transgender women keep their penises, some do not.

Just respect your new Trans woman for who she is individually and try not to stereotype her. That way your chances of a long-term relationship with a beautiful Transgender woman have just increased many fold!


Just an average guy and admin of MyLadyboyCupid.